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List of benzodiazepines

January 01, 1970

The tables below contain a sample list of benzodiazepines and benzodiazepine analogs that are commonly prescribed, with their basic pharmacological characteristics, such as half-life and equivalent doses to other benzodiazepines, also listed, along with their trade names and primary uses. The elimination half-life is how long it takes for half of the drug to be eliminated by the body. "Time to peak" refers to when maximum levels of the drug in the blood occur after a given dose. Benzodiazepines generally share the same pharmacological properties, such as anxiolytic, sedative, hypnotic, skeletal muscle relaxant, amnesic, and anticonvulsant effects. Variation in potency of certain effects may exist amongst individual benzodiazepines. Some benzodiazepines produce active metabolites. Active metabolites are produced when a person's body metabolizes the drug into compounds that share a similar pharmacological profile to the parent compound and thus are relevant when calculating how long the pharmacological effects of a drug will last. Long-acting benzodiazepines with long-acting active metabolites, such as diazepam and chlordiazepoxide, are often prescribed for benzodiazepine or alcohol withdrawal as well as for anxiety if constant dose levels are required throughout the day. Shorter-acting benzodiazepines are often preferred for insomnia due to their lesser hangover effect.[1][2][3][4][5]

It is fairly important to note that elimination half-life of diazepam and chlordiazepoxide, as well as other long half-life benzodiazepines, is twice as long in the elderly compared to younger individuals. Due to increased sensitivity and potentially dangerous adverse events among elderly patients, it is recommended to avoid prescribing them as specified by the 2015 American Geriatrics Society Beers Criteria.[6] Individuals with an impaired liver also metabolize benzodiazepines more slowly. Thus, the approximate equivalent of doses below may need to be adjusted accordingly in individuals on short acting benzodiazepines who metabolize long-acting benzodiazepines more slowly and vice versa. The changes are most notable with long acting benzodiazepines as these are prone to significant accumulation in such individuals and can lead to withdrawal symptoms.[citation needed] For example, the equivalent dose of diazepam in an elderly individual on lorazepam may be half of what would be expected in a younger individual.[7][8] Equivalent doses of benzodiazepines differ as much as 20 fold.[9][10][11]

Pharmacokinetic properties of various benzodiazepines edit

Equivalency data in the table below is taken from the Ashton "Benzodiazepine Equivalence Table".[4][12][13][14]

Drug Name Common Trade Names[a] Year Approved

(US FDA)

Typical Oral Dosage Formulations

(mg)

Approx. Equivalent Oral Dose to 10 mg Diazepam[b] (mg) Peak Onset of Action

(hours)

Elimination Half-life of Active Metabolite (hours) Primary Therapeutic Use
Adinazolam Deracyn Research chemical 1–2 3 anxiolytic, antidepressant
Alprazolam Xanax, Helex, Xanor, Trankimazin, Onax, Alprox, Misar, Restyl, Solanax, Tafil, Neurol, Frontin, Kalma, Ksalol, Farmapram 1981 0.25, 0.5, 1, 2 0.5 1–3[16] 11-13 [10–20][16] anxiolytic, antidepressant[17]
Bentazepam[c] Thiadipona 25 1–3 2–4 anxiolytic
Bretazenil[18] 2.5 anxiolytic, anticonvulsant
Bromazepam Lexotanil, Lexotan, Lexilium, Lectopam, Lexaurin, Lexatin, Bromam 1981 1.5, 3, 6 6 1–5 20–40 anxiolytic,

hypnotic, muscle relaxant

Bromazolam Research chemical 2 , 4 2 anxiolytic
Brotizolam[d] Lendormin, Dormex, Sintonal, Noctilan 0.25 0.5 0.5–2 4–5 hypnotic
Camazepam Albego, Limpidon 40[19] 1–3 6–11 anxiolytic
Chlordiazepoxide Librium, Risolid, Elenium 1960 5, 10, 25 25 1.5–6 36–200 anxiolytic
Cinazepam Levana 0.5, 1, 2 2–4 60 hypnotic, anxiolytic
Cinolazepam Gerodorm 40 0.5–2 9 hypnotic
Clobazam Onfi, Frisium, Urbanol 2011 5, 10, 20 20 1–5 8–60 anxiolytic, anticonvulsant
Clonazepam Rivatril, Rivotril, Klonopin, Iktorivil, Paxam 1975 0.5, 1, 2 0.5-1 1–5 19.5–50 anticonvulsant, anxiolytic
Clonazolam Research chemical 0.25, 0.5 0.2 0.5-1 3-4[20] hypnotic, anticonvulsant
Clorazepate Tranxene, Tranxilium 1972 3.75, 5, 7.5 15 Variable 32–152 anxiolytic, anticonvulsant
Clotiazepam[c] Veratran, Clozan, Rize 5, 10 10 1–3 4 anxiolytic
Cloxazolam Cloxam, Sepazon, Olcadil 1, 2, 4 1.5[19] 2–5 55–77[19] anxiolytic, anticonvulsant
Delorazepam Dadumir 0.5, 1, 2 1-1.5 1–2 79<[21] anxiolytic, amnesic
Deschloroetizolam[d] Research chemical 1, 2 4 anxiolytic
Diazepam Antenex, Apaurin, Apzepam, Apozepam, Diazepan, Hexalid, Normabel, Pax, Stesolid, Stedon, Tranquirit, Valium, Vival, Valaxona 1963 2, 5, 10 10 1–1.5 32–205 anxiolytic, anticonvulsant, muscle relaxant, amnesic
Diclazepam[22] Research chemical 1, 2 2 1.5–3 42 anxiolytic, muscle relaxant
Estazolam ProSom, Nuctalon 1990 1, 2 2[19] 3–5 10–24 hypnotic, anxiolytic
Ethyl carfluzepate Not approved 2 1–5 11–24 hypnotic
Etizolam[d] Etilaam, Etizest, Pasaden, Depas Often sold as a research chemical, but is approved for human use in many countries. Controlled substance in some US states, Canada, Germany, Austria, and others.[23][24] 1 2 1–3 5-7 anxiolytic, muscle relaxant, anticonvulsant
Ethyl loflazepate Victan, Meilax, Ronlax 2[19] 2.5–3 73–119 anxiolytic
Flualprazolam Research chemical 0.5, 1 0.25 1-2 12-22 anxiolytic, hypnotic
Flubromazepam[25] Templex Research chemical 4, 8, 12 4 1.5–8 100–220 anxiolytic, hypnotic, amnesic, muscle relaxant, anticonvulsant
Flubromazolam Remnon Research chemical 0.25, 0.5 0.075 0.5-5 10-20[26] hypnotic
Fluclotizolam[d] Research chemical 0.25-0.5 anxiolytic
Flunitrazepam Rohypnol, Hipnosedon, Vulbegal, Fluscand, Flunipam, Ronal, Rohydorm, Hypnodorm 1972 1, 2 1.5 0.5–3 18–200 hypnotic
Flunitrazolam Research chemical 0.25, 0.5 0.1 0.5-1 5-13 hypnotic
Flurazepam Dalmadorm, Dalmane, Fluzepam 1970 30 20-25 1–1.5 40–250 hypnotic
Flutazolam Coreminal 4 10 1-3 47-100 hypnotic
Flutemazepam Research chemical 1 0.5-5 8-20 hypnotic, anxiolytic, anticonvulsant, muscle relaxant[27]
Flutoprazepam Restas 1984 1, 2 2.5 0.5–9 87[28] hypnotic, anticonvulsant, muscle relaxant
Halazepam Alapryl, Paxipam 1981 20, 40 40 3–6 15-35 [30-100] anxiolytic
Ketazolam Anxon, Sedotime 1980 15, 30, 45 20 2.5–6 30-100 [36-200] anxiolytic
Loprazolam Dormonoct, Havlane 1983 1, 2 1.5 2–5 6–20[29] hypnotic
Lorazepam Ativan, Orfidal, Lorenin, Lorsilan, Temesta, Tavor, Lorabenz 1977 0.5, 1, 2, 2.5 1 2–4 10–20 anxiolytic, anticonvulsant, hypnotic, muscle relaxant[30][14][31]
Lormetazepam Loramet, Noctamid, Pronoctan 1984 1, 2 1.5 0.5–2 10-12 hypnotic, anxiolytic
Meclonazepam Research chemical 6 anxiolytic
Medazepam Nobrium, Ansilan, Mezapam, Rudotel, Raporan 10 10 4-8 36–200 anxiolytic
Metizolam[d] Research chemical 1, 2, 4 2–4 12 anxiolytic
Mexazolam Melex, Sedoxil 0.5, 1 1–2 anxiolytic
Midazolam Dormicum, Flormidal, Versed, Hypnovel, Dormonid 1985 7.5, 15 10 (oral)

4 (IV)

0.5–1 1.8-6 hypnotic, anticonvulsant
Nifoxipam Research chemical 0.5, 1, 2 hypnotic
Nimetazepam Erimin, Lavol 1984 5 2.5-5 0.5–3 14–30 hypnotic
Nitemazepam Research chemical 2 0.5-5 10-27 hypnotic, anticonvulsant
Nitrazepam Mogadon, Alodorm, Pacisyn, Dumolid, Nitrazadon 1965 5, 10 5 0.5–7 17–48 hypnotic, anticonvulsant
Nitrazolam Research chemical 0.5, 1 hypnotic
Nordazepam Madar, Stilny 5, 7.5, 15 10-15 30–150 anxiolytic
Norflurazepam Research chemical 5 47-100 hypnotic
Oxazepam Seresta, Serax, Serenid, Serepax, Sobril, Oxabenz, Oxapax, Oxascand, Ox-Pam, Opamox, Alepam, Medopam, Murelax, Noripam, Purata 1965 10, 15, 30, 50 30 3–4 4–11 anxiolytic
Phenazepam Phenazepam, Phenzitat Research chemical 1.5–4 60 anxiolytic, anticonvulsant
Pinazepam Domar, Duna 5, 10 40–100 anxiolytic
Prazepam Demetrin, Lysanxia, Prazene, Centrax 1976 10, 20, 30 15-20 2–6 36–200 anxiolytic
Premazepam Not approved 15 2–6 10–13 anxiolytic
Pyrazolam Research chemical 0.25, 0.5, 1 1–1.5 16–18[32] anxiolytic, amnesic
Quazepam Doral, Quiedorm 1985 15 20 1–5 39–120 hypnotic
Rilmazafone Rhythmy 11 hypnotic
Temazepam Restoril, Normison, Euhypnos, Temaze, Tenox 1981 10, 20 15-20 0.5–3 4–11 hypnotic, anxiolytic, muscle relaxant
Tetrazepam Myolastan, Clinoxam, Epsipam, Musaril 50 1–3 3–26 muscle relaxant, anxiolytic
Triazolam Halcion, Rilamir, Notison, Somese 1980 0.125, 0.25 0.5 0.5–2 2 hypnotic
Drug Name Common Trade Names Year Approved Typical Dosages of Oral Tablets

(mg)

Approx. Equivalent Oral Dose to 10mg Diazepam (mg) Peak onset of action (hours) Elimination Half-life of Active Metabolite (hours) Primary Therapeutic Use

Atypical benzodiazepine receptor ligands edit

Drug Name Common Trade Names Year approved(US FDA) Elimination Half-life

of Active Metabolite (hours)

Primary Therapeutic Use
DMCM anxiogenic, convulsant
Flumazenil[e] Anexate, Lanexat, Mazicon, Romazicon 1 antidote
Eszopiclone§ Lunesta 2004 6 hypnotic
Zaleplon§ Sonata, Starnoc 1999 1 hypnotic
Zolpidem§ Ambien, Nytamel, Sanval, Stilnoct, Stilnox, Sublinox (Canada), Xolnox, Zoldem, Zolnod 1992 2.6 hypnotic
Zopiclone§ Imovane, Rhovane, Ximovan; Zileze; Zimoclone; Zimovane; Zopitan; Zorclone, Zopiklone 4–6 hypnotic
  1. ^ Not all trade names are listed.
  2. ^ An alternative table published by the state of South Australia uses equivalent approximate oral dosages to 5 mg diazepam.[15]
  3. ^ a b Technically this is a thienodiazepine, but produces very similar effects as benzodiazepines.
  4. ^ a b c d e Technically this is a thienotriazolodiazepine, but produces very similar effects as benzodiazepines.
  5. ^ Flumazenil is an imidazobenzodiazepine derivative,[33] and in layman's terms, it is a benzodiazepine overdose antidote that is given intravenously in Intensive Care Units (ICUs) to reverse the effects of benzodiazepine overdoses, as well for overdoses of the non-benzodiazepine "Z-drugs" such as zolpidem.[34] Flumazenil is contraindicated for benzodiazepine-tolerant patients in overdose cases.[34] In such cases, the benefits are far outweighed by the risks, which include potential and severe seizures.[33][35] The method by which flumazenil acts to prevent non-benzodiazepine tolerant overdose from causing potential harm is via preventing the benzodiazepines and Z-drugs from binding to the GABAA receptors via competitive inhibition which the flumazenil creates. Clinical observation notating the patient's oxygen levels, respiratory, heart and blood pressure rates are used, as they are much safer than the potential seizure effects from flumazenil. Supportive care to mediate any problems resulting from abnormal rates of the pulmonary, respiratory, and cardiovascular systems is typically the only treatment that is required in benzodiazepine-only overdoses.[36] In most cases, activated charcoal/carbon is often used to prevent benzodiazepines from being absorbed by the gastrointestinal tract, and the use of stomach-pumping/gastric lavage is no longer commonly used nor suggested by some toxicologists.[37] Even in cases where other central nervous system (CNS) depressants (such as in combined benzodiazepine and tricyclic antidepressant/TCA overdoses) are detected and/or suspected, endotrachial intubation for the airway path and supportive oxygen are typically implemented and are much safer than flumazenil.[36]

Controversy edit

In 2015 the UK's House of Commons attempted to get a two to four week limit mandate for prescribing benzodiazepines to replace the two to four week benzodiazepine prescribing guidelines, which are merely recommended.[38]

Binding data and structure-activity relationship edit

 
A variety of Benzodiazepines along with their molecular structure.

A large number of benzodiazepine derivatives have been synthesised and their structure-activity relationships explored in detail.[39][40][41][42] This chart contains binding data for benzodiazepines and related drugs investigated by Roche up to the late 1990s (though in some cases the compounds were originally synthesised by other companies such as Takeda or Upjohn).[43][44][45][46][47][48] Other benzodiazepines are also listed for comparison purposes,[49][50][51] but it does not however include binding data for;

While binding or activity data are available for most of these compounds also, the assay conditions vary between sources, meaning that in many cases the values are not suitable for a direct comparison. Many older sources used animal measures of activity (i.e. sedation or anticonvulsant activity) but did not measure in vitro binding to benzodiazepine receptors.[57][58] See for instance Table 2 vs Table 11 in the Chem Rev paper, Table 2 lists in vitro pIC50 values matching those below, while Table 11 has pEC50 values derived from in vivo assays in mice, which show the same activity trends but cannot be compared directly, and includes data for compounds such as diclazepam and flubromazepam which are not available in the main data set.


Also note;

  • IC50 / pIC50 values represent binding affinity only and do not reflect efficacy or pharmacokinetics, and some compounds listed are GABAA antagonists rather than agonists (e.g. flumazenil).
  • Low IC50 or high pIC50 values indicate tighter binding (pIC50 of 8.0 = IC50 of 10nM, pIC50 of 9.0 = IC50 of 1nM, etc.)
  • These are non subtype selective IC50 values averaged across all GABAA receptor subtypes, so subtype selective compounds with strong binding at one subtype but weak at others will appear unusually weak due to averaging of binding values (see e.g. CL-218,872)
  • † indicates a predicted value from in silico modelling.[59]
  • Finally, note that the benzodiazepine core is a privileged scaffold, which has been used to derive drugs with diverse activity that is not limited to the GABAA modulatory action of the classical benzodiazepines,[60] such as devazepide and tifluadom, however these have not been included in the list below. 2,3-benzodiazepines such as tofisopam are also not listed, as these act primarily as AMPA receptor modulators, and are inactive at GABAA receptors.


See also edit

References edit

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Further reading edit

  • Gitlow S (1 October 2006). Substance Use Disorders: A Practical Guide (2nd ed.). USA: Lippincott Williams and Wilkins. p. 110. ISBN 978-0-7817-6998-3.
  • Galanter M, Kleber HD (1 July 2008). The American Psychiatric Publishing Textbook of Substance Abuse Treatment (4th ed.). United States of America: American Psychiatric Publishing Inc. p. 216. ISBN 978-1-58562-276-4.

January 01, 1970
list, benzodiazepines, tables, below, contain, sample, list, benzodiazepines, benzodiazepine, analogs, that, commonly, prescribed, with, their, basic, pharmacological, characteristics, such, half, life, equivalent, doses, other, benzodiazepines, also, listed, . The tables below contain a sample list of benzodiazepines and benzodiazepine analogs that are commonly prescribed with their basic pharmacological characteristics such as half life and equivalent doses to other benzodiazepines also listed along with their trade names and primary uses The elimination half life is how long it takes for half of the drug to be eliminated by the body Time to peak refers to when maximum levels of the drug in the blood occur after a given dose Benzodiazepines generally share the same pharmacological properties such as anxiolytic sedative hypnotic skeletal muscle relaxant amnesic and anticonvulsant effects Variation in potency of certain effects may exist amongst individual benzodiazepines Some benzodiazepines produce active metabolites Active metabolites are produced when a person s body metabolizes the drug into compounds that share a similar pharmacological profile to the parent compound and thus are relevant when calculating how long the pharmacological effects of a drug will last Long acting benzodiazepines with long acting active metabolites such as diazepam and chlordiazepoxide are often prescribed for benzodiazepine or alcohol withdrawal as well as for anxiety if constant dose levels are required throughout the day Shorter acting benzodiazepines are often preferred for insomnia due to their lesser hangover effect 1 2 3 4 5 It is fairly important to note that elimination half life of diazepam and chlordiazepoxide as well as other long half life benzodiazepines is twice as long in the elderly compared to younger individuals Due to increased sensitivity and potentially dangerous adverse events among elderly patients it is recommended to avoid prescribing them as specified by the 2015 American Geriatrics Society Beers Criteria 6 Individuals with an impaired liver also metabolize benzodiazepines more slowly Thus the approximate equivalent of doses below may need to be adjusted accordingly in individuals on short acting benzodiazepines who metabolize long acting benzodiazepines more slowly and vice versa The changes are most notable with long acting benzodiazepines as these are prone to significant accumulation in such individuals and can lead to withdrawal symptoms citation needed For example the equivalent dose of diazepam in an elderly individual on lorazepam may be half of what would be expected in a younger individual 7 8 Equivalent doses of benzodiazepines differ as much as 20 fold 9 10 11 Contents 1 Pharmacokinetic properties of various benzodiazepines 1 1 Atypical benzodiazepine receptor ligands 1 2 Controversy 2 Binding data and structure activity relationship 3 See also 4 References 5 Further readingPharmacokinetic properties of various benzodiazepines editEquivalency data in the table below is taken from the Ashton Benzodiazepine Equivalence Table 4 12 13 14 Drug Name Common Trade Names a Year Approved US FDA Typical Oral Dosage Formulations mg Approx Equivalent Oral Dose to 10 mg Diazepam b mg Peak Onset of Action hours Elimination Half life of Active Metabolite hours Primary Therapeutic Use Adinazolam Deracyn Research chemical 1 2 3 anxiolytic antidepressant Alprazolam Xanax Helex Xanor Trankimazin Onax Alprox Misar Restyl Solanax Tafil Neurol Frontin Kalma Ksalol Farmapram 1981 0 25 0 5 1 2 0 5 1 3 16 11 13 10 20 16 anxiolytic antidepressant 17 Bentazepam c Thiadipona 25 1 3 2 4 anxiolytic Bretazenil 18 2 5 anxiolytic anticonvulsant Bromazepam Lexotanil Lexotan Lexilium Lectopam Lexaurin Lexatin Bromam 1981 1 5 3 6 6 1 5 20 40 anxiolytic hypnotic muscle relaxant Bromazolam Research chemical 2 4 2 anxiolytic Brotizolam d Lendormin Dormex Sintonal Noctilan 0 25 0 5 0 5 2 4 5 hypnotic Camazepam Albego Limpidon 40 19 1 3 6 11 anxiolytic Chlordiazepoxide Librium Risolid Elenium 1960 5 10 25 25 1 5 6 36 200 anxiolytic Cinazepam Levana 0 5 1 2 2 4 60 hypnotic anxiolytic Cinolazepam Gerodorm 40 0 5 2 9 hypnotic Clobazam Onfi Frisium Urbanol 2011 5 10 20 20 1 5 8 60 anxiolytic anticonvulsant Clonazepam Rivatril Rivotril Klonopin Iktorivil Paxam 1975 0 5 1 2 0 5 1 1 5 19 5 50 anticonvulsant anxiolytic Clonazolam Research chemical 0 25 0 5 0 2 0 5 1 3 4 20 hypnotic anticonvulsant Clorazepate Tranxene Tranxilium 1972 3 75 5 7 5 15 Variable 32 152 anxiolytic anticonvulsant Clotiazepam c Veratran Clozan Rize 5 10 10 1 3 4 anxiolytic Cloxazolam Cloxam Sepazon Olcadil 1 2 4 1 5 19 2 5 55 77 19 anxiolytic anticonvulsant Delorazepam Dadumir 0 5 1 2 1 1 5 1 2 79 lt 21 anxiolytic amnesic Deschloroetizolam d Research chemical 1 2 4 anxiolytic Diazepam Antenex Apaurin Apzepam Apozepam Diazepan Hexalid Normabel Pax Stesolid Stedon Tranquirit Valium Vival Valaxona 1963 2 5 10 10 1 1 5 32 205 anxiolytic anticonvulsant muscle relaxant amnesic Diclazepam 22 Research chemical 1 2 2 1 5 3 42 anxiolytic muscle relaxant Estazolam ProSom Nuctalon 1990 1 2 2 19 3 5 10 24 hypnotic anxiolytic Ethyl carfluzepate Not approved 2 1 5 11 24 hypnotic Etizolam d Etilaam Etizest Pasaden Depas Often sold as a research chemical but is approved for human use in many countries Controlled substance in some US states Canada Germany Austria and others 23 24 1 2 1 3 5 7 anxiolytic muscle relaxant anticonvulsant Ethyl loflazepate Victan Meilax Ronlax 2 19 2 5 3 73 119 anxiolytic Flualprazolam Research chemical 0 5 1 0 25 1 2 12 22 anxiolytic hypnotic Flubromazepam 25 Templex Research chemical 4 8 12 4 1 5 8 100 220 anxiolytic hypnotic amnesic muscle relaxant anticonvulsant Flubromazolam Remnon Research chemical 0 25 0 5 0 075 0 5 5 10 20 26 hypnotic Fluclotizolam d Research chemical 0 25 0 5 anxiolytic Flunitrazepam Rohypnol Hipnosedon Vulbegal Fluscand Flunipam Ronal Rohydorm Hypnodorm 1972 1 2 1 5 0 5 3 18 200 hypnotic Flunitrazolam Research chemical 0 25 0 5 0 1 0 5 1 5 13 hypnotic Flurazepam Dalmadorm Dalmane Fluzepam 1970 30 20 25 1 1 5 40 250 hypnotic Flutazolam Coreminal 4 10 1 3 47 100 hypnotic Flutemazepam Research chemical 1 0 5 5 8 20 hypnotic anxiolytic anticonvulsant muscle relaxant 27 Flutoprazepam Restas 1984 1 2 2 5 0 5 9 87 28 hypnotic anticonvulsant muscle relaxant Halazepam Alapryl Paxipam 1981 20 40 40 3 6 15 35 30 100 anxiolytic Ketazolam Anxon Sedotime 1980 15 30 45 20 2 5 6 30 100 36 200 anxiolytic Loprazolam Dormonoct Havlane 1983 1 2 1 5 2 5 6 20 29 hypnotic Lorazepam Ativan Orfidal Lorenin Lorsilan Temesta Tavor Lorabenz 1977 0 5 1 2 2 5 1 2 4 10 20 anxiolytic anticonvulsant hypnotic muscle relaxant 30 14 31 Lormetazepam Loramet Noctamid Pronoctan 1984 1 2 1 5 0 5 2 10 12 hypnotic anxiolytic Meclonazepam Research chemical 6 anxiolytic Medazepam Nobrium Ansilan Mezapam Rudotel Raporan 10 10 4 8 36 200 anxiolytic Metizolam d Research chemical 1 2 4 2 4 12 anxiolytic Mexazolam Melex Sedoxil 0 5 1 1 2 anxiolytic Midazolam Dormicum Flormidal Versed Hypnovel Dormonid 1985 7 5 15 10 oral 4 IV 0 5 1 1 8 6 hypnotic anticonvulsant Nifoxipam Research chemical 0 5 1 2 hypnotic Nimetazepam Erimin Lavol 1984 5 2 5 5 0 5 3 14 30 hypnotic Nitemazepam Research chemical 2 0 5 5 10 27 hypnotic anticonvulsant Nitrazepam Mogadon Alodorm Pacisyn Dumolid Nitrazadon 1965 5 10 5 0 5 7 17 48 hypnotic anticonvulsant Nitrazolam Research chemical 0 5 1 hypnotic Nordazepam Madar Stilny 5 7 5 15 10 15 30 150 anxiolytic Norflurazepam Research chemical 5 47 100 hypnotic Oxazepam Seresta Serax Serenid Serepax Sobril Oxabenz Oxapax Oxascand Ox Pam Opamox Alepam Medopam Murelax Noripam Purata 1965 10 15 30 50 30 3 4 4 11 anxiolytic Phenazepam Phenazepam Phenzitat Research chemical 1 5 4 60 anxiolytic anticonvulsant Pinazepam Domar Duna 5 10 40 100 anxiolytic Prazepam Demetrin Lysanxia Prazene Centrax 1976 10 20 30 15 20 2 6 36 200 anxiolytic Premazepam Not approved 15 2 6 10 13 anxiolytic Pyrazolam Research chemical 0 25 0 5 1 1 1 5 16 18 32 anxiolytic amnesic Quazepam Doral Quiedorm 1985 15 20 1 5 39 120 hypnotic Rilmazafone Rhythmy 11 hypnotic Temazepam Restoril Normison Euhypnos Temaze Tenox 1981 10 20 15 20 0 5 3 4 11 hypnotic anxiolytic muscle relaxant Tetrazepam Myolastan Clinoxam Epsipam Musaril 50 1 3 3 26 muscle relaxant anxiolytic Triazolam Halcion Rilamir Notison Somese 1980 0 125 0 25 0 5 0 5 2 2 hypnotic Drug Name Common Trade Names Year Approved Typical Dosages of Oral Tablets mg Approx Equivalent Oral Dose to 10mg Diazepam mg Peak onset of action hours Elimination Half life of Active Metabolite hours Primary Therapeutic Use Atypical benzodiazepine receptor ligands edit Drug Name Common Trade Names Year approved US FDA Elimination Half life of Active Metabolite hours Primary Therapeutic Use DMCM anxiogenic convulsant Flumazenil e Anexate Lanexat Mazicon Romazicon 1 antidote Eszopiclone Lunesta 2004 6 hypnotic Zaleplon Sonata Starnoc 1999 1 hypnotic Zolpidem Ambien Nytamel Sanval Stilnoct Stilnox Sublinox Canada Xolnox Zoldem Zolnod 1992 2 6 hypnotic Zopiclone Imovane Rhovane Ximovan Zileze Zimoclone Zimovane Zopitan Zorclone Zopiklone 4 6 hypnotic Not all trade names are listed An alternative table published by the state of South Australia uses equivalent approximate oral dosages to 5 mg diazepam 15 a b Technically this is a thienodiazepine but produces very similar effects as benzodiazepines a b c d e Technically this is a thienotriazolodiazepine but produces very similar effects as benzodiazepines Flumazenil is an imidazobenzodiazepine derivative 33 and in layman s terms it is a benzodiazepine overdose antidote that is given intravenously in Intensive Care Units ICUs to reverse the effects of benzodiazepine overdoses as well for overdoses of the non benzodiazepine Z drugs such as zolpidem 34 Flumazenil is contraindicated for benzodiazepine tolerant patients in overdose cases 34 In such cases the benefits are far outweighed by the risks which include potential and severe seizures 33 35 The method by which flumazenil acts to prevent non benzodiazepine tolerant overdose from causing potential harm is via preventing the benzodiazepines and Z drugs from binding to the GABAA receptors via competitive inhibition which the flumazenil creates Clinical observation notating the patient s oxygen levels respiratory heart and blood pressure rates are used as they are much safer than the potential seizure effects from flumazenil Supportive care to mediate any problems resulting from abnormal rates of the pulmonary respiratory and cardiovascular systems is typically the only treatment that is required in benzodiazepine only overdoses 36 In most cases activated charcoal carbon is often used to prevent benzodiazepines from being absorbed by the gastrointestinal tract and the use of stomach pumping gastric lavage is no longer commonly used nor suggested by some toxicologists 37 Even in cases where other central nervous system CNS depressants such as in combined benzodiazepine and tricyclic antidepressant TCA overdoses are detected and or suspected endotrachial intubation for the airway path and supportive oxygen are typically implemented and are much safer than flumazenil 36 Controversy edit In 2015 the UK s House of Commons attempted to get a two to four week limit mandate for prescribing benzodiazepines to replace the two to four week benzodiazepine prescribing guidelines which are merely recommended 38 Binding data and structure activity relationship edit nbsp A variety of Benzodiazepines along with their molecular structure A large number of benzodiazepine derivatives have been synthesised and their structure activity relationships explored in detail 39 40 41 42 This chart contains binding data for benzodiazepines and related drugs investigated by Roche up to the late 1990s though in some cases the compounds were originally synthesised by other companies such as Takeda or Upjohn 43 44 45 46 47 48 Other benzodiazepines are also listed for comparison purposes 49 50 51 but it does not however include binding data for Benzodiazepines developed in the former Soviet Union e g phenazepam gidazepam etc Benzodiazepines predominantly used only in Japan e g nimetazepam flutoprazepam etc 4 5 cyclised benzodiazepines e g ketazolam cloxazolam etc and other compounds not researched by Roche Benzodiazepines developed more recently e g remimazolam QH ii 066 Ro48 6791 etc Designer benzodiazepines for which in vitro binding data are unavailable e g flubromazolam pyrazolam etc 52 53 54 55 56 While binding or activity data are available for most of these compounds also the assay conditions vary between sources meaning that in many cases the values are not suitable for a direct comparison Many older sources used animal measures of activity i e sedation or anticonvulsant activity but did not measure in vitro binding to benzodiazepine receptors 57 58 See for instance Table 2 vs Table 11 in the Chem Rev paper Table 2 lists in vitro pIC50 values matching those below while Table 11 has pEC50 values derived from in vivo assays in mice which show the same activity trends but cannot be compared directly and includes data for compounds such as diclazepam and flubromazepam which are not available in the main data set Also note IC50 pIC50 values represent binding affinity only and do not reflect efficacy or pharmacokinetics and some compounds listed are GABAA antagonists rather than agonists e g flumazenil Low IC50 or high pIC50 values indicate tighter binding pIC50 of 8 0 IC50 of 10nM pIC50 of 9 0 IC50 of 1nM etc These are non subtype selective IC50 values averaged across all GABAA receptor subtypes so subtype selective compounds with strong binding at one subtype but weak at others will appear unusually weak due to averaging of binding values see e g CL 218 872 indicates a predicted value from in silico modelling 59 Finally note that the benzodiazepine core is a privileged scaffold which has been used to derive drugs with diverse activity that is not limited to the GABAA modulatory action of the classical benzodiazepines 60 such as devazepide and tifluadom however these have not been included in the list below 2 3 benzodiazepines such as tofisopam are also not listed as these act primarily as AMPA receptor modulators and are inactive at GABAA receptors Table of benzodiazepines click to Chemical structure Code pIC50 IC50 Chemical name PubChem CAS number nbsp Ro05 3061 7 3979 40nM 7 fluoro 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 75849 2648 00 2 nbsp Ro05 4865 7 7696 17nM 7 fluoro 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 44366179 nbsp Ro05 6820 8 1308 7 4nM 7 fluoro 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 44366116 nbsp Ro05 6822 8 2924 5 1nM 7 fluoro 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 23275675 2024 34 2 nbsp Iso flubromazepam 7 fluoro 5 2 bromophenyl 1H benzo e 1 4 diazepin 2 3H one 15292433 153873 96 2 nbsp Nordazepam 8 0269 9 4nM 7 chloro 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 2997 1088 11 5 nbsp Diazepam 8 0915 8 1nM 7 chloro 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 3016 439 14 5 nbsp Norflurazepam Ro05 3367 8 699 7 chloro 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 4540 2886 65 9 nbsp Fludiazepam 7 chloro 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 3369 3900 31 0 nbsp Ro07 3953 8 7959 1 6nM 7 chloro 5 2 6 difluorophenyl 1H benzo e 1 4 diazepin 2 3H one 23275763 nbsp Difludiazepam Ro07 4065 8 3872 4 1nM 7 chloro 5 2 6 difluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 44366236 39080 67 6 nbsp Delorazepam 8 7447 1 8nM 7 chloro 5 2 chlorophenyl 1H benzo e 1 4 diazepin 2 3H one 17925 2894 67 9 nbsp Diclazepam Ro05 3448 7 8 7 chloro 5 2 chlorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 76168 2894 68 0 nbsp Ro05 4864 TSPO ligand 7 chloro 5 4 chlorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 1688 14439 61 3 nbsp Ro07 5193 8 5229 7 chloro 5 2 chloro 6 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 44366219 nbsp Ro22 3294 8 1549 7 chloro 5 2 6 dichlorophenyl 1H benzo e 1 4 diazepin 2 3H one 12790028 nbsp Ro07 5220 8 2596 7 chloro 5 2 6 dichlorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 9975396 30144 88 8 nbsp 7 BPDBD 7 8 7 bromo 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 76167 2894 61 3 nbsp QH II 063 7 bromo 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 627432 28611 28 1 nbsp Phenazepam 8 4 7 bromo 5 2 chlorophenyl 1H benzo e 1 4 diazepin 2 3H one 40113 51753 57 2 nbsp Flubromazepam JYI 42 7 6 7 bromo 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 12947024 2647 50 9 nbsp Flubrometazepam 7 bromo 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 135809 86890 79 1 nbsp SH I 048A 3S 7 bromo 5 2 fluorophenyl 3 methyl 1H benzo e 1 4 diazepin 2 3H one 49850464 872874 11 8 nbsp Gidazepam 6 4 2 7 bromo 2 oxo 5 phenyl 2 3 dihydro 1H benzo e 1 4 diazepin 1 yl acetohydrazide 121919 129186 29 4 nbsp Ro13 3780 8 6198 7 bromo 5 2 6 difluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 9975396 103380 73 0 nbsp Ro07 9749 7 iodo 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 3082318 30843 56 2 nbsp Ro07 9957 8 5376 7 iodo 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 118749 nbsp Ro05 2904 7 8861 13nM 7 trifluoromethyl 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 16795 2285 16 7 nbsp Ro14 3074 8 2757 5 3nM 7 azido 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one nbsp Nitrazepam 8 0 10nM 7 nitro 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 4506 146 22 5 nbsp Nimetazepam 7 nitro 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 4496 2011 67 8 nbsp Ro05 4435 8 829 1 5nM 7 nitro 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 520217 2558 30 7 nbsp Flunitrazepam 8 4202 3 8nM 7 nitro 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 3380 1622 62 4 nbsp Clonazepam 8 7447 1 8nM 7 nitro 5 2 chlorophenyl 1H benzo e 1 4 diazepin 2 3H one 2802 1622 61 3 nbsp Ro05 4082 8 6576 7 nitro 5 2 chlorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 528222 5527 71 9 nbsp Ro05 3590 8 4559 3 5nM 7 nitro 5 2 trifluoromethyl phenyl 1H benzo e 1 4 diazepin 2 3H one 15024 1427 45 8 nbsp QH 146 7 nitro 5 2 nitrophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 44383992 nbsp Ro20 7736 7 0177 96nM 7 hydroxyamino 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro05 3072 6 4134 386nM 7 amino 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 78641 4928 02 3 nbsp Ro05 4318 6 3372 460nM 7 amino 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 23275339 4959 16 4 nbsp Ro20 1815 7 1871 65nM 7 amino 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 92294 34084 50 9 nbsp Ro05 4619 7 1249 75nM 7 amino 5 2 chlorophenyl 1H benzo e 1 4 diazepin 2 3H one 188298 4959 17 5 Ro05 3308 IC50 gt 1000nM N 2 oxo 5 phenyl 2 3 dihydro 1H benzo e 1 4 diazepin 7 yl acetamide Ro12 6377 7 1249 455nM 1 5 2 fluorophenyl 1 methyl 2 oxo 2 5 dihydro 1H benzo e 1 4 diazepin 7 yl 3 methylurea nbsp Ro05 9090 IC50 gt 1000nM 7 aminomethyl 1 methyl 5 phenyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro05 3343 IC50 gt 1000nM N N dimethyl 2 oxo 5 phenyl 2 3 dihydro 1H benzo e 1 4 diazepine 7 sulfonamide 214460 12037 79 5 nbsp Ro05 4528 6 4202 380nM 7 cyano 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro20 2541 7 5229 30nM 7 cyano 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro20 2533 7 4437 36nM 7 ethyl 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 10264786 nbsp Ro20 5747 7 6198 24nM 7 vinyl 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 44366036 nbsp QH ii 066 7 4 7 ethynyl 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 9838431 183239 39 6 nbsp OMB 18 7 ethynyl 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 89276170 nbsp XLI 352 7 ethynyl 5 2 chlorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 21065236 nbsp Ro20 5397 7 3665 43nM 7 formyl 5 phenyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro20 3053 7 7447 18nM 7 acetyl 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 21828109 nbsp Ro05 2921 6 4559 350nM 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 76175 2898 08 0 nbsp Ro05 3663 IC50 gt 1000nM 5 methyl 1H benzo e 1 4 diazepin 2 3H one 5080 70656 87 0 nbsp Ro05 4336 7 6778 21nM 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 13292074 nbsp Ro07 4419 7 7212 19nM 5 2 6 difluorophenyl 1H benzo e 1 4 diazepin 2 3H one 44366255 nbsp Ro05 4520 7 8539 14nM 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 193319 844 11 1 nbsp Ro05 4608 8 4202 5 2 chlorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 10469149 nbsp Ro05 3546 6 4949 320nM 6 chloro 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 14590445 nbsp Ro13 0699 6 8239 150nM 6 chloro 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 44377764 nbsp Ro07 6198 7 5528 28nM 8 chloro 5 2 6 difluorophenyl 1H benzo e 1 4 diazepin 2 3H one 23275762 nbsp Ro20 8895 7 7212 19nM 8 methyl 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 44366169 nbsp Ro13 0593 7 1427 72nM 9 chloro 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro13 0882 IC50 300nM 6 8 dichloro 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro22 6762 7 3979 40nM 7 8 dichloro 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 44366089 nbsp Ro20 8065 8 4437 3 6nM 7 8 dichloro 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 10358803 88695 06 1 nbsp Ro20 8552 7 8539 14nM 7 methyl 8 chloro 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 44366138 nbsp Ro05 2750 7 4318 37nM 6 8 dichloro 5 phenyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro14 2312 IC50 gt 1000nM 6 amino 8 chloro 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one Ro07 3609 7 284 nbsp Ro11 8125 7 4318 37nM 5 2 chlorophenyl 1H thieno 2 3 e 1 4 diazepin 2 3H one nbsp Ro08 6739 IC50 70nM 7 chloro 5 phenyl 1H thieno 2 3 e 1 4 diazepin 2 3H one nbsp Ro09 9212 8 4089 3 9nM 7 chloro 5 2 chlorophenyl 1H thieno 2 3 e 1 4 diazepin 2 3H one 135721042 nbsp Ro10 2643 IC50 9 4nM 7 chloro 5 2 chlorophenyl 1H thieno 3 2 e 1 4 diazepin 2 3H one nbsp Clotiazepam 7 ethyl 5 2 chlorophenyl 1 methyl 1H thieno 2 3 e 1 4 diazepin 2 3H one 2811 33671 46 4 nbsp Bentazepam 8 5 5 phenyl 3 5a 6 7 8 9 hexahydro 2H 1 benzothieno 2 3 e 1 4 diazepin 2 3H one 34592 29462 18 8 nbsp Lopirazepam 7 chloro 5 2 chlorophenyl 3 hydroxy 1 3 dihydro 2H pyrido 3 2 e 1 4 diazepin 2 one 68672 42863 81 0 nbsp Premazepam 6 7696 170nM 6 7 dimethyl 5 phenyl 3 7 dihydropyrrolo 3 4 e 1 4 diazepin 2 1H one 72104 57435 86 6 nbsp Ripazepam 1 ethyl 3 methyl 8 phenyl 4 6 dihydropyrazolo 4 3 e 1 4 diazepin 5 1H one 33474 26308 28 1 nbsp Zolazepam 1 3 8 trimethyl 4 2 fluorophenyl 6 8 dihydropyrazolo 3 4 e 1 4 diazepin 7 1H one 35775 31352 82 6 nbsp Zomebazam 8 1 1 3 8 trimethyl 4 phenyl 6 8 dihydropyrazolo 4 3 b 1 4 diazepine 5 7 1H 4H dione 132677 78466 70 3 nbsp Ro17 2221 6 585 260nM 1 2 aminoethyl 5 phenyl 1H benzo e 1 4 diazepin 2 3H one Ro07 5096 IC50 gt 1000nM 2 7 chloro 5 2 fluorophenyl 2 oxo 2 3 dihydro 1H benzo e 1 4 diazepin 1 yl acetic acid Ro08 3026 7 2007 nbsp Halazepam 7 0362 92nM 7 chloro 5 phenyl 1 2 2 2 trifluoroethyl 1H benzo e 1 4 diazepin 2 3H one 31640 23092 17 3 nbsp Quazepam 7 chloro 5 2 fluorophenyl 1 2 2 2 trifluoroethyl 1H benzo e 1 4 diazepin 2 3H thione 4999 36735 22 5 nbsp Fletazepam 7 chloro 5 2 fluorophenyl 1 2 2 2 trifluoroethyl 1H benzo e 1 4 diazepine 36834 34482 99 0 nbsp Pinazepam 7 0339 92 5nM 7 chloro 5 phenyl 1 prop 2 yn 1 yl 1H benzo e 1 4 diazepin 2 3H one 40391 52463 83 9 nbsp Prazepam IC50 110nM 7 chloro 5 phenyl 1 cyclopropylmethyl 1H benzo e 1 4 diazepin 2 3H one 4890 2955 38 6 nbsp Flutoprazepam 6 6 7 chloro 5 2 fluorophenyl 1 cyclopropylmethyl 1H benzo e 1 4 diazepin 2 3H one 3400 25967 29 7 nbsp Cloniprazepam 7 8 7 nitro 5 2 chlorophenyl 1 cyclopropylmethyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro20 1310 6 2076 620nM 7 chloro 5 phenyl 1 t butyl 1H benzo e 1 4 diazepin 2 3H one nbsp Fosazepam 7 chloro 5 phenyl 1 dimethylphosphorylmethyl 1H benzo e 1 4 diazepin 2 3H one 37114 35322 07 7 nbsp Iclazepam 7 chloro 5 phenyl 1 2 cyclopropylmethoxy ethyl 1H benzo e 1 4 diazepin 2 3H one 68777 57916 70 8 nbsp Tolufazepam 7 chloro 5 2 chlorophenyl 1 2 4 methylphenyl sulfonylethyl 1H benzo e 1 4 diazepin 2 3H one 65647 86273 92 9 nbsp Elfazepam 6 9 7 chloro 5 2 fluorophenyl 1 2 ethylsulfonylethyl 1H benzo e 1 4 diazepin 2 3H one 65445 52042 01 0 nbsp Reclazepam 2 7 chloro 5 2 chlorophenyl 2 3 dihydro 1H 1 4 benzodiazepin 1 yl 1 3 oxazol 4 5H one 3052777 76053 16 2 nbsp Ro07 1986 8 0809 8 3nM 1 2 aminoethyl 7 chloro 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one nbsp Flurazepam 7 8297 7 chloro 1 2 diethylamino ethyl 5 2 fluorophenyl 1 3 dihydro 2H 1 4 benzodiazepin 2 one 3393 17617 23 1 nbsp Ro07 2750 7 6108 24 5nM 7 chloro 5 2 fluorophenyl 1 2 hydroxyethyl 1H benzo e 1 4 diazepin 2 3H one nbsp Motrazepam IC50 430nM 1 methoxymethyl 7 nitro 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 65764 29442 58 8 Ro08 9013 7 3716 nbsp Proflazepam 6 8539 140nM 7 chloro 1 2 3 dihydroxypropyl 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 3050433 52829 30 8 nbsp Ro22 4683 6 5229 300nM 7 nitro 5 2 fluorophenyl 1 t butyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro15 8852 6 1391 726nM 5 2 chlorophenyl 4 methyl 7 nitro 4 5 dihydro 1H benzo e 1 4 diazepin 2 3H one nbsp Chlorodiazepoxide 6 4535 352nM 7 chloro 2 methylamino 5 phenyl 3H benzo e 1 4 diazepine 4 oxide 2712 58 25 3 nbsp Cyprazepam 7 chloro N cyclopropylmethyl 4 hydroxy 5 phenyl 3H benzo e 1 4 diazepin 2 imine 27452 15687 07 7 nbsp Uldazepam 7 6 7 chloro 5 2 chlorophenyl N prop 2 enoxy 3H benzo e 1 4 diazepin 2 amine 34274 28546 58 9 nbsp Demoxepam 6 5086 310nM 7 chloro 1 3 dihydro 5 phenyl 2H benzo e 1 4 diazepin 2 one 4 oxide 13756 963 39 3 nbsp Medazepam IC50 870nM 7 chloro 5 phenyl 1 methyl 1H benzo e 1 4 diazepine 4041 2898 12 6 nbsp Tuclazepam 7 7 7 chloro 5 2 chlorophenyl 2 hydroxymethyl 1 methyl 2 3 dihydro 1H benzo e 1 4 diazepine 3050405 51037 88 8 nbsp Metaclazepam 7 bromo 5 2 chlorophenyl 2 methoxymethyl 1 methyl 2 3 dihydro 1H benzo e 1 4 diazepine 71272 84031 17 4 nbsp Sulazepam 7 7 7 chloro 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H thione 17931 2898 13 7 nbsp Tetrazepam 7 4685 34nM 7 chloro 5 cyclohexen 1 yl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 25215 10379 14 3 nbsp Nortetrazepam IC50 34nM 7 chloro 5 cyclohexen 1 yl 1H benzo e 1 4 diazepin 2 3H one 166581 10379 11 0 nbsp Menitrazepam 7 nitro 5 cyclohexen 1 yl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 189875 28781 64 8 nbsp Ro05 3328 7 0605 87nM 7 chloro 5 cyclohexyl 1H benzo e 1 4 diazepin 2 3H one nbsp Clazolam 8 1 2 chloro 5 methyl 5 9 10 14b tetrahydroisoquino 2 1 d 1 4 benzodiazepin 6 7H one 24107 7492 29 7 nbsp Bromazepam 7 7447 18nM 7 bromo 5 pyridin 2 yl 1H benzo e 1 4 diazepin 2 3H one 2441 1812 30 2 nbsp Methylbromazepam 7 bromo 5 pyridin 2 yl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 630183 1812 33 5 nbsp Pyridazino diazepam 7 chloro 5 pyridazin 3 yl 1 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp SCHEMBL9684958 7 chloro 5 1H pyrazol 5 yl 1H benzo e 1 4 diazepin 2 3H one 21738192 nbsp Compound 6a 9 5 7 chloro 5 3 5 dimethyl 4H 1 2 4 triazol 4 yl 1 3 dihydro 2H 1 4 benzodiazepin 2 one nbsp JC 184 7 bromo 5 2 thienyl 1H benzo e 1 4 diazepin 2 3H one 21065240 nbsp BDBM50083903 7 chloro 5 2 furanyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 10423506 Ro05 5605 6 5376 Ro11 3129 8 1871 2 amino N 2 2 chlorobenzoyl 4 nitrophenyl propanamide 21413751 65607 70 7 Ro03 7355 6 3768 nbsp Ro11 4878 8 4559 3 5nM 7 chloro 5 2 fluorophenyl 3 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp Meclonazepam 8 9208 1 2nM 3S 7 nitro 5 2 chlorophenyl 3 methyl 1H benzo e 1 4 diazepin 2 3H one 3033985 58662 84 3 nbsp Ro11 6896 8 1549 7nM 7 nitro 5 2 fluorophenyl 1 3 dimethyl 1H benzo e 1 4 diazepin 2 3H one nbsp Ro06 7263 7 3098 49nM 1 7 dichloro 5 phenyl 3 methyl 1H benzo e 1 4 diazepin 2 3H one nbsp Oxazepam 7 7447 18nM 7 chloro 3 hydroxy 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 4616 604 75 1 nbsp Temazepam 7 7959 16nM 7 chloro 3 hydroxy 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 5391 846 50 4 nbsp Lorazepam 8 4559 3 5nM 7 chloro 3 hydroxy 5 2 chlorophenyl 1H benzo e 1 4 diazepin 2 3H one 3958 846 49 1 nbsp Lormetazepam 7 chloro 3 hydroxy 5 2 chlorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 13314 848 75 9 nbsp Flutemazepam 8 1 7 chloro 3 hydroxy 5 2 fluorophenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 40344 52391 89 6 nbsp Cinolazepam 7 chloro 3 hydroxy 5 2 fluorophenyl 1 2 cyanoethyl 1H benzo e 1 4 diazepin 2 3H one 3033621 75696 02 5 nbsp Doxefazepam 7 chloro 3 hydroxy 5 2 fluorophenyl 1 2 hydroxyethyl 1H benzo e 1 4 diazepin 2 3H one 38668 40762 15 0 nbsp Nifoxipam 8 5 7 nitro 3 hydroxy 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one 3058221 74723 10 7 nbsp Nitemazepam 7 nitro 3 hydroxy 5 phenyl 1 methyl 1H benzo e 1 4 diazepin 2 3H one 12362353 40762 03 6 nbsp 3 Hydroxyphenazepam 8 7 7 bromo 3 hydroxy 5 2 chlorophenyl 1H benzo e 1 4 diazepin 2 3H one 125820 70030 11 4 nbsp Cinazepam 7 bromo 3 succinyloxy 5 2 chlorophenyl 1H benzo e 1 4 diazepin 2 3H one 629281 172986 25 3 nbsp Pivoxazepam 7 chloro 3 pivalyloxy 5 phenyl 1H benzo e 1 4 diazepin 2 3H one 68722 55299 10 0 nbsp Camazepam 6 0458 7 chloro 1 methyl 2 oxo 5 phenyl 2 3 dihydro 1H benzo e 1 4 diazepin 3 yl N N dimethylcarbamate 37367 36104 80 0 nbsp Clorazepate IC50 59nM 7 chloro 2 oxo 5 phenyl 1H benzo e 1 4 diazepine 3 carboxylic acid 2809 23887 31 2 nbsp Nitrazepate 7 nitro 2 oxo 5 phenyl 1H benzo e 1 4 diazepine 3 carboxylic acid 21740 5571 84 6 nbsp Ethyl carfluzepate 8 0 ethyl 7 chloro 5 2 fluorophenyl 1 methylcarbamoyl 2 oxo 3H benzo e 1 4 diazepine 3 carboxylate 68856 65400 85 3 nbsp Ethyl dirazepate 7 5 ethyl 7 chloro 5 2 chlorophenyl 2 oxo 3H benzo e 1 4 diazepine 3 carboxylate 208941 23980 14 5 nbsp Ethyl loflazepate ethyl 7 chloro 5 2 fluorophenyl 2 oxo 3H benzo e 1 4 diazepine 3 carboxylate 3299 29177 84 2 nbsp Carburazepam 7 9 7 chloro 1 methyl 2 oxo 5 phenyl 1 2 3 5 tetrahydro 4H benzo e 1 4 diazepine 4 carboxamide 68787 59009 93 7 nbsp Ro20 7078 8 2757 5 3nM 3 7 dichloro 5 2 fluorophenyl 1H benzo e 1 4 diazepin 2 3H one nbsp Clobazam 6 8861 130nM 7 chloro 1 methyl 5 phenyl 1H 1 5 benzodiazepine 2 4 3H 5H dione 2789 22316 47 8 nbsp Desmethylclobazam 6 6778 210nM 7 chloro 5 phenyl 1H 1 5 benzodiazepine 2 4 3H 5H dione nbsp Triflubazam 8 4 7 trifluoromethyl 1 methyl 5 phenyl 1H 1 5 benzodiazepine 2 4 3H 5H dione 2789 22316 47 8 nbsp Lofendazam 7 chloro 5 phenyl 1 3 4 5 tetrahydro 4H 1 5 benzodiazepin 4 one 71709 29176 29 2 nbsp Arfendazam 8 3 ethyl 7 chloro 4 oxo 5 phenyl 2 3 dihydro 1 5 benzodiazepine 1 carboxylate 65803 37669 57 1 nbsp CP 1414S 7 9 8 nitro 1 phenyl 4 amino 3H 1 5 benzodiazepin 2 one 37594 36975 99 2 nbsp Compound 6i 8 6 9 chloro 11 phenyl 6 11 dihydro 5H pyrimido 4 5 b 1 5 benzodiazepin 5 one nbsp Oxazolam 10 chloro 2 methyl 11b phenyl 2 3 7 11b tetrahydrobenzo f oxazolo 3 2 d 1 4 diazepin 6 5H one 62779 24143 17 7 nbsp Cloxazolam 10 chloro 11b 2 chlorophenyl 2 3 5 7 tetrahydro 1 3 oxazolo 3 2 d 1 4 benzodiazepin 6 5H one 2816 24166 13 0 nbsp Mexazolam 10 chloro 11b 2 chlorophenyl 3 methyl 2 3 7 11b tetrahydro 1 3 oxazolo 3 2 d 1 4 benzodiazepin 6 5H one 4177 31868 18 5 nbsp Flutazolam 10 chloro 11b 2 fluorophenyl 7 2 hydroxyethyl 3 5 dihydro 2H 1 3 oxazolo 3 2 d 1 4 benzodiazepin 6 5H one 3398 27060 91 9 nbsp Haloxazolam 10 bromo 11b 2 fluorophenyl 2 3 5 7 tetrahydro 1 3 oxazolo 3 2 d 1 4 benzodiazepin 6 5H one 3563 59128 97 1 nbsp Ketazolam 11 chloro 8 12b dihydro 2 8 dimethyl 12b phenyl 4H 1 3 oxazino 3 2 d 1 4 benzodiazepine 4 7 6H dione 33746 27223 35 4 nbsp U 35005 8 3665 4 3nM 6 2 chlorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 21680194 nbsp Estazolam 8 0706 8 5nM 8 chloro 6 phenyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 3261 29975 16 4 nbsp Alprazolam 7 699 20nM 8 chloro 6 phenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 2118 28981 97 7 nbsp Triazolam 8 3979 4nM 8 chloro 6 2 chlorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 5556 28911 01 5 nbsp alpha Hydroxytriazolam 8 3768 4 2nM 8 chloro 6 2 chlorophenyl 1 hydroxymethyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 1963 37115 45 0 nbsp Flualprazolam 8 3 8 chloro 6 2 fluorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 10359044 28910 91 0 nbsp Iso flualprazolam 8 fluoro 6 2 chlorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine nbsp Desmethyltriazolam 8 3 8 chloro 6 2 chlorophenyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 826660 42292 42 2 nbsp Nitrazolam 8 5 8 nitro 6 phenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 20317278 28910 99 8 nbsp Desmethylnitrazolam 8 8 8 nitro 6 phenyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 20317280 30858 58 3 nbsp Clonazolam 9 5 8 nitro 6 2 chlorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 12317881 33887 02 4 nbsp Flunitrazolam 8 8 8 nitro 6 2 fluorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 137700379 2243815 18 9 nbsp Flubromazolam JYI 73 8 8 8 bromo 6 2 fluorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 21930924 612526 40 6 nbsp Fluiodomazolam BDBM50011621 8 iodo 6 2 fluorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 14851835 nbsp Triflumazolam SCHEMBL7327294 8 trifluoromethyl 6 phenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 19010444 nbsp JYI 70 8 ethynyl 6 2 fluorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 14851900 nbsp XLI 296 8 ethynyl 6 2 chlorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 14851901 nbsp Clobromazolam DM II 90 8 2 8 bromo 6 2 chlorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 1032830 87213 50 1 nbsp Bromazolam XLI 268 8 5 8 bromo 6 phenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 12562546 71368 80 4 nbsp Pyrazolam SH I 04 8 1 8 bromo 6 pyridin 2 yl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 12562545 39243 02 2 nbsp Pyclazolam 8 2 8 chloro 6 pyridin 2 yl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 20368150 nbsp Pynazolam 9 4 8 nitro 6 pyridin 2 yl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 20368157 2034366 97 5 nbsp Pyeazolam SH TRI 108 7 9 8 ethynyl 6 pyridin 2 yl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 71811108 1349115 59 8 nbsp Adinazolam 6 8697 135nM 8 chloro 6 phenyl 1 N N dimethylaminomethyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 37632 37115 32 5 nbsp U 42352 8 chloro 6 phenyl 1 N methylaminomethyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 119094 37115 33 6 nbsp Fluadinazolam 7 1 8 chloro 6 2 fluorophenyl 1 N N dimethylaminomethyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 21537253 37391 59 6 nbsp U 43465 F 7 9431 8 chloro 1 2 dimethylamino ethyl 6 phenyl 4H s triazolo 4 3 a 1 4 benzodiazepine 134388 83983 74 8 nbsp Ro11 5073 8 4815 3 3nM 4S 8 chloro 6 2 fluorophenyl 1 4 dimethyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine 101637147 nbsp Ro11 6679 8 3979 4nM 8 nitro 6 2 fluorophenyl 1 4 dimethyl 4H benzo f 1 2 4 triazolo 4 3 a 1 4 diazepine nbsp Ro17 4582 8 4559 3 5nM 4 2 chlorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine nbsp Etizolam 8 5086 3 1nM 2 ethyl 4 2 chlorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 3307 40054 69 1 nbsp Deschloroetizolam 8 5 2 ethyl 4 phenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 827322 40054 73 7 nbsp Desmethyletizolam 2 ethyl 4 2 chlorophenyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 12434325 40054 68 0 nbsp Fluetizolam 8 8 2 ethyl 4 2 fluorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 12434320 40054 88 4 nbsp Nitizolam 2 nitro 4 2 chlorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 70600959 nbsp Iprotizolam 2 isopropyl 4 2 chlorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 67727941 nbsp Clotizolam Ro11 1465 8 8539 1 4nM 2 chloro 4 2 chlorophenyl 9 methyl 4H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 3041455 54123 06 7 nbsp Deschloroclotizolam 2 chloro 4 phenyl 9 methyl 4H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 157010678 1629324 97 5 nbsp Fluclotizolam 9 1 2 chloro 4 2 fluorophenyl 9 methyl 4H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 21317700 54123 15 8 nbsp Difluclotizolam 2 chloro 4 2 6 difluorophenyl 9 methyl 4H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 21317683 nbsp Brotizolam 8 9208 2 bromo 4 2 chlorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 2451 57801 81 7 nbsp Flubrotizolam LS 152 574 9 6 2 bromo 4 2 fluorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 3044878 57801 95 3 nbsp Ro14 1636 8 8239 2 iodo 4 2 chlorophenyl 9 methyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 14851924 nbsp Ciclotizolam 8 0 2 bromo 4 2 chlorophenyl 9 cyclohexyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepine 71949 58765 21 2 Ro11 7800 8 5376 2 9nM 2 chloro 4 2 chlorophenyl 6H thieno 3 2 f 1 2 4 triazolo 4 3 a 1 4 diazepin 9 yl methanamine nbsp Zapizolam 8 8 8 chloro 6 2 chlorophenyl 4H pyrido 2 3 f 1 2 4 triazolo 4 3 a 1 4 diazepine 68832 64098 32 4 nbsp Rilmazolam LS 188 599 7 3 8 chloro 6 2 chlorophenyl N N dimethyl 4H 1 2 4 triazolo 1 5 a 1 4 benzodiazepine 2 carboxamide 148494 50330 59 1 nbsp Midazolam 8 3188 4 8nM 8 chloro 6 2 fluorophenyl 1 methyl 4H imidazo 1 5 a 1 4 benzodiazepine 4192 59467 70 8 nbsp alpha Hydroxymidazolam 8 3468 4 5nM 8 chloro 6 2 fluorophenyl 1 hydroxymethyl 4H imidazo 1 5 a 1 4 benzodiazepine 107917 59468 90 5 nbsp Ro22 0284 8 chloro 6 2 fluorophenyl 1 hydroxymethyl 4 hydroxy 4H imidazo 1 5 a 1 4 benzodiazepine 10316307 64740 68 7 nbsp Climazolam 8 1 8 chloro 6 2 chlorophenyl 1 methyl 4H imidazo 1 5 a 1 4 benzodiazepine 68790 59467 77 5 nbsp Remimazolam 8 3 methyl 3 4S 8 bromo 1 methyl 6 pyridin 2 yl 4H imidazo 1 2 a 1 4 benzodiazepin 4 yl propanoate 9824461 308242 62 8 nbsp Ro15 8670 7 8239 15nM ethyl 8 chloro 6 phenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 14907889 nbsp JYI 32 ethyl 8 bromo 6 2 fluorophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 21930922 nbsp JY XHE 057 ethyl 8 ethynyl 6 2 fluorophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 21065283 nbsp Ro16 0529 7 8539 14nM tert butyl 7 chloro 6 phenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate nbsp Ro21 5205 8 1308 7 4nM methyl 8 chloro 6 2 fluorophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 12801973 nbsp SH 053 R CH3 2 F 7 9 ethyl 4R 8 ethynyl 6 2 fluorophenyl 4 methyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 11574585 872874 14 1 nbsp HZ 166 ethyl 8 ethynyl 6 pyridin 2 yl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10309028 612527 56 7 nbsp MP III 022 9 1 4R 8 ethynyl 6 2 fluorophenyl N 4 dimethyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide 130439777 nbsp GL II 73 4R 8 ethynyl 6 2 fluorophenyl N N 4 trimethyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide 130439778 nbsp YT III 31 8 ethynyl 6 phenyl N methyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide 49848318 Ro22 1892 7 9208 12nM 8 chloro 6 2 fluorophenyl 3 isopropoxycarbonyl 4H benzo f imidazo 1 5 a 1 4 diazepine 5 oxide nbsp Ro22 0992 7 8861 13nM 8 chloro 6 2 chlorophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylic acid nbsp Ro21 8137 8 4559 3 5nM 8 chloro 6 2 fluorophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide nbsp Ro21 8384 8 4202 8 chloro 6 2 chlorophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide 162997 63176 94 3 nbsp Imidazenil 8 8 8 fluoro 6 2 bromophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide 119194 151271 08 8 nbsp Ro23 0364 6 2 chlorophenyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide 194998 113066 25 4 nbsp Ro21 8482 7 585 26nM 8 chloro 6 2 chlorophenyl 1 dimethylamino methyl 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide nbsp Loprazolam 8 2007 2Z 6 2 chlorophenyl 2 4 methyl 1 piperazinyl methylene 8 nitro 2 4 dihydro 1H imidazo 1 2 a 1 4 benzodiazepin 1 one 3033860 61197 73 7 nbsp Fluloprazolam 8 0 2Z 6 2 fluorophenyl 2 4 methyl 1 piperazinyl methylene 8 nitro 2 4 dihydro 1H imidazo 1 2 a 1 4 benzodiazepin 1 one 12371485 nbsp PS I 35 2Z 6 phenyl 2 4 methyl 1 piperazinyl methylene 8 bromo 2 4 dihydro 1H imidazo 1 2 a 1 4 benzodiazepin 1 one 72660859 Ro14 1359 7 1549 70nM 7 chloro 5 2 fluorophenyl 1H benzo b azepin 2 3H one Ro15 8867 7 6021 25nM 7 nitro 5 2 chlorophenyl 1H benzo b azepin 2 3H one nbsp Ro14 7187 6 3872 410nM 1 methyl 6 phenyl 4H benzo f 1 2 4 triazolo 4 3 a azepine 85687871 Ro13 9868 7 3768 42nM 8 chloro 1 methyl 6 phenyl 4H benzo f 1 2 4 triazolo 4 3 a azepine nbsp Ro14 5921 7 7212 19nM 8 chloro 6 2 fluorophenyl 4H benzo f 1 2 4 triazolo 4 3 a azepine 20449965 nbsp Ro14 0304 8 1871 6 5nM 8 chloro 6 2 fluorophenyl 1 methyl 4H benzo f 1 2 4 triazolo 4 3 a azepine 20449964 Ro14 2652 8 2518 5 6nM 8 chloro 6 2 fluorophenyl 4H benzo f 1 2 4 triazolo 4 3 a azepin 1 yl methanamine nbsp Ro15 9270 8 301 5nM 6 2 chlorophenyl 1 methyl 8 nitro 4H benzo f 1 2 4 triazolo 4 3 a azepine 20450010 Ro14 0609 7 6126 24 4nM 8 chloro 6 2 fluorophenyl 5 6 dihydro 4H benzo f 1 2 4 triazolo 4 3 a azepine Ro15 2201 8 8239 1 5nM methyl 6 phenyl 4H benzo f imidazo 1 5 a azepine 3 carboxylate Ro15 0791 8 6021 2 5nM ethyl 6 phenyl 4H benzo f imidazo 1 5 a azepine 3 carboxylate Ro15 2200 8 3768 4 2nM ethyl 6 2 fluorophenyl 4H benzo f imidazo 1 5 a azepine 3 carboxylate Ro14 3929 7 7959 16nM ethyl 8 chloro 6 2 fluorophenyl 4H benzo f imidazo 1 5 a azepine 3 carboxylate Ro14 3930 7 8239 15nM 8 chloro 6 2 fluorophenyl 4H benzo f imidazo 1 5 a azepine 3 carboxamide Ro14 5568 6 6383 230nM 8 chloro 6 2 fluorophenyl 4H benzo f imidazo 1 5 a azepine nbsp Ro22 1274 7 1249 75nM 8 chloro 1 2 fluorophenyl 3H benzo c azepine 13271760 89376 31 8 Ro22 1251 7 9586 11nM 9 chloro 2 methyl 7 phenyl 5H benzo c pyrimido 4 5 e azepine Ro22 1366 8 3979 4nM 9 chloro 7 2 fluorophenyl 2 methyl 5H benzo c pyrimido 4 5 e azepine Ro22 2038 8 5528 2 8nM 9 chloro 7 2 fluorophenyl 5H benzo c pyrimido 4 5 e azepin 2 amine Ro22 3245 8 5528 2 8nM 9 chloro 7 2 chlorophenyl 5H benzo c pyrimido 4 5 e azepine Ro22 3148 6 3768 420nM 6 phenyl 2 4 dihydrobenzo c 1 2 3 triazolo 4 5 e azepine Ro22 3147 8 284 5 2nM 6 2 chlorophenyl 2 4 dihydrobenzo c 1 2 3 triazolo 4 5 e azepine Ro22 0780 7 9586 11nM 8 chloro 6 phenyl 2 4 dihydrobenzo c 1 2 3 triazolo 4 5 e azepine Ro22 2466 8 7212 1 9nM 8 chloro 6 2 fluorophenyl 2 4 dihydrobenzo c 1 2 3 triazolo 4 5 e azepine Ro22 2468 8 6021 nbsp Ro22 8515 8 chloro 6 2 chlorophenyl 1 4 dihydropyrrolo 3 4 d 2 benzazepin 3 2H one 145981 nbsp Ro14 5974 8 1938 6 4nM S ethyl 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate 10041121 88552 32 3 nbsp Ro15 4941 8 7696 1 7nM S ethyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate nbsp Ro14 5975 7 2076 62nM S ethyl 7 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate nbsp Ro16 3607 7 3372 46nM S tert butyl 8 methoxy 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate nbsp Ro16 6624 8 10nM S tert butyl 8 ethyl 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate nbsp Ro16 3774 8 4949 3 2nM S tert butyl 8 methyl 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 0071 8 4949 3 2nM S tert butyl 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 5824 8 4685 3 4nM S tert butyl 8 methylthio 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 8912 8 2076 6 2nM S tert butyl 8 fluoro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 4261 8 1135 7 7nM S tert butyl 7 fluoro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 0075 8 6021 Ro16 6127 8 5086 3 1nM S tert butyl 8 chloro 7 fluoro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 3058 7 0458 nbsp Bretazenil 8 6576 S tert butyl 8 bromo 9 oxo 11 12 13 13a tetrahydro 9H imidazo 1 5 a pyrrolo 2 1 c 1 4 benzodiazepine 1 carboxylate 107926 84379 13 5 nbsp EVT 201 7 chloro 3 5 dimethylamino methyl 1 2 4 oxadiazol 3 yl 5 methyl 4 5 dihydro 6H imidazo 1 5 a 1 4 benzodiazepin 6 one 9885841 308239 86 3 nbsp FG 8205 7 chloro 5 methyl 3 5 propan 2 yl 1 2 4 oxadiazol 3 yl 4H imidazo 1 5 a 1 4 benzodiazepin 6 one 129710 122384 14 9 nbsp L 655 708 ethyl 13aS 7 methoxy 9 oxo 11 12 13 13a tetrahydro 9H imidazo 1 5 a pyrrolo 2 1 c 1 4 benzodiazepine 1 carboxylate 5311203 130477 52 0 nbsp PWZ 029 8 chloro 3 methoxymethyl 5 methyl 4H imidazo 1 5 a 1 4 benzodiazepin 6 one 9971547 nbsp Ro48 6791 8 fluoro 5 methyl 3 5 dipropylamino methyl 1 2 4 oxadiazol 3 yl 4H imidazo 1 5 a 1 4 benzodiazepin 6 one 9953485 172407 17 9 nbsp Ro48 8684 8 fluoro 5 methyl 3 5 dipropylamino methyl 1 3 oxazol 2 yl 4H imidazo 1 5 a 1 4 benzodiazepin 6 one 9866317 nbsp Ro4882224 3 10 dichloro 9H benzo f imidazo 1 5 a 1 2 4 triazolo 1 5 d 1 4 diazepine 11673720 nbsp Ro4938581 3 bromo 10 difluoromethyl 9H benzo f imidazo 1 5 a 1 2 4 triazolo 1 5 d 1 4 diazepine 11624499 883093 10 5 Ro16 6605 8 6778 Ro16 6048 8 4815 3 3nM S tert butyl 9 oxo 8 trifluoromethyl 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 6950 8 5528 2 8nM S tert butyl 8 nitro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 4019 8 8539 1 4nM S propyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 3031 8 6021 2 5nM S isopropyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 9906 8 7696 1 7nM S allyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 7081 8 585 Ro16 7082 8 2007 6 3nM S isobutyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 7083 8 5376 2 9nM 13aS sec butyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 9918 8 6383 2 3nM S cyclopropylmethyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro16 4020 8 585 Ro16 6654 8 3979 4nM S cyclohexyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro17 3206 8 4685 Ro17 3207 8 284 Ro16 4021 8 8239 Ro17 1302 8 2757 5 3nM S phenyl 8 chloro 9 oxo 11 12 13 13a tetrahydro 9H benzo e imidazo 5 1 c pyrrolo 1 2 a 1 4 diazepine 1 carboxylate Ro15 2427 IC50 gt 1000nM 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxamide nbsp Ro14 7437 8 5229 3nM ethyl 5 methyl 6 oxo 4H imidazo 1 5 a 1 4 benzodiazepine 3 carboxylate 127597 83210 63 3 nbsp Sarmazenil Ro15 3505 8 5686 2 7nM ethyl 7 chloro 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 71231 78771 13 8 nbsp Ro15 1310 8 1675 6 8nM ethyl 8 chloro 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 114888 78756 33 9 nbsp Ro15 1746 IC50 gt 1000nM ethyl 9 chloro 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate nbsp Ro15 3237 IC50 gt 1000nM ethyl 10 chloro 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate Ro15 5623 8 699 nbsp Flumazenil 8 6021 ethyl 8 fluoro 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 3373 78755 81 4 nbsp Ro15 4513 ethyl 8 azido 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 5081 91917 65 6 nbsp RY 031 ethyl 8 ethyl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10245056 nbsp TG 4 29 ethyl 8 vinyl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10591116 nbsp RY 080 ethyl 8 ethynyl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 5311418 nbsp YT II 76 ethyl 8 cyclopropyl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 46214569 nbsp SVO 8 14 ethyl 8 allyl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 15316982 nbsp SVO 8 30 ethyl 8 furan 2 yl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 15316986 nbsp SVO 8 67 ethyl 8 phenyl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 15316984 nbsp TG 4 39 ethyl 8 thiophen 2 yl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 15316985 nbsp CD 214 cyclopropyl 8 chloro 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 101652266 nbsp DM 139 t butyl 8 pyrrolidin 1 yl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10547937 nbsp DM 146 t butyl 8 piperidin 1 yl 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10834569 nbsp DM 173 t butyl 8 dimethylamino 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10808192 nbsp DM 215 t butyl 8 methoxy 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10807310 nbsp Ro19 4603 t butyl 5 6 dihydro 5 methyl 6 oxo 4H imidazo 1 5 a thieno 2 3 f 1 4 diazepine 3 carboxylate 127382 99632 94 7 nbsp Iomazenil ethyl 7 iodo 5 methyl 6 oxo 5 6 dihydro 4H benzo f imidazo 1 5 a 1 4 diazepine 3 carboxylate 10251042 127985 21 1 Ro17 9741 8 6198 2 4nM S methyl 8 chloro 9 oxo 9 11 12 12a tetrahydroazeto 1 2 a benzo e imidazo 5 1 c 1 4 diazepine 1 carboxylate Ro16 0858 8 8861 ethyl 8 chloro 9 oxo 12 12a dihydro 9H 11H azeto 1 2 a benzo e imidazo 5 1 c 1 4 diazepine 1 carboxylate Ro16 0153 8 2757 tert butyl 8 chloro 9 oxo 12 12a dihydro 9H 11H azeto 2 1 c benzo e imidazo 1 5 a 1 4 diazepine 1 carboxylate nbsp Ro17 1812 8 8861 S cyclopropylmethyl 8 chloro 9 oxo 9 11 12 12a tetrahydroazeto 1 2 a benzo e imidazo 5 1 c 1 4 diazepine 1 carboxylate 146197 90450 01 4 Ro17 3211 8 62 Ro17 3401 9 0458 Ro17 3620 8 2924 Ro16 9351 8 4318 Ro16 9905 8 9208 Ro17 1338 9 nbsp Zopiclone 7 5086 6 5 chloropyridin 2 yl 7 oxo 6 7 dihydro 5H pyrrolo 3 4 b pyrazin 5 yl 4 methylpiperazine 1 carboxylate 5735 43200 80 2 nbsp Suriclone 8 6778 6 7 chloro 1 8 naphthyridin 2 yl 5 oxo 3 7 dihydro 2H 1 4 dithiino 2 3 c pyrrol 7 yl 4 methylpiperazine 1 carboxylate 40903 53813 83 5 nbsp CL 218 872 6 9208 3 methyl 6 3 trifluoromethyl phenyl 1 2 4 triazolo 3 4 f pyridazine 107950 66548 69 4 nbsp GBLD 345 9 2 4 aminophenyl 3 methoxy N 3 methoxyphenyl methyl imidazo 2 1 f pyridazin 6 amine 4602899 122479 08 7See also editBenzodiazepine Benzodiazepine dependence Benzodiazepine withdrawal syndromeReferences edit Golombok S Lader M August 1984 The psychopharmacological effects of premazepam diazepam and placebo in healthy human subjects British Journal of Clinical Pharmacology 18 2 127 133 doi 10 1111 j 1365 2125 1984 tb02444 x PMC 1463527 PMID 6148956 de Visser SJ van der Post JP de Waal PP Cornet F Cohen AF van Gerven JM January 2003 Biomarkers for the effects of benzodiazepines in healthy volunteers British Journal of Clinical Pharmacology 55 1 39 50 doi 10 1046 j 1365 2125 2002 t01 10 01714 x PMC 1884188 PMID 12534639 Benzodiazepine Names non benzodiazepines org uk Archived from the original on 2008 12 08 Retrieved 2009 04 05 a b Ashton CH March 2007 Benzodiazepine Equivalence Table benzo org uk Retrieved 2009 04 05 Hsiung R July 1995 Benzodiazepine Equivalence Charts dr bob org Archived from the original on 2009 02 09 Retrieved 2009 04 05 By the American Geriatrics Society 2015 Beers Criteria Update Expert Panel et al American Geriatrics Society 2015 Beers Criteria Update Expert Panel November 2015 American Geriatrics Society 2015 Updated Beers Criteria for Potentially Inappropriate Medication Use in Older Adults Journal of the American Geriatrics Society 63 11 2227 2246 doi 10 1111 jgs 13702 PMID 26446832 S2CID 38797655 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint numeric names authors list link Salzman C 15 May 2004 Clinical geriatric psychopharmacology 4th ed USA Lippincott Williams amp Wilkins pp 450 453 ISBN 978 0 7817 4380 8 Delco F Tchambaz L Schlienger R Drewe J Krahenbuhl S 2005 Dose adjustment in patients with liver disease Drug Safety 28 6 529 545 doi 10 2165 00002018 200528060 00005 PMID 15924505 S2CID 9849818 Riss J Cloyd J Gates J Collins S August 2008 Benzodiazepines in epilepsy pharmacology and pharmacokinetics Acta Neurologica Scandinavica 118 2 69 86 doi 10 1111 j 1600 0404 2008 01004 x PMID 18384456 S2CID 24453988 Ashton H July 1994 Guidelines for the rational use of benzodiazepines When and what to use Drugs 48 1 25 40 doi 10 2165 00003495 199448010 00004 PMID 7525193 S2CID 46966796 benzo org uk Benzodiazepines How They Work amp How to 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benzodiazepine drug in normal subjects European Journal of Drug Metabolism and Pharmacokinetics 14 4 293 298 doi 10 1007 BF03190114 PMID 2633923 S2CID 20710732 Swift CG Swift MR Ankier SI Pidgen A Robinson J August 1985 Single dose pharmacokinetics and pharmacodynamics of oral loprazolam in the elderly British Journal of Clinical Pharmacology 20 2 119 128 doi 10 1111 j 1365 2125 1985 tb05041 x PMC 1400680 PMID 2864049 Shah D Borrensen D 2011 Benzodiazepines A Guide to Safe Prescribing PDF The Carlat Report Psychiatry Archived from the original PDF on 2015 07 01 Retrieved 2015 06 28 Vancouver Hospital Pharmaceutical Sciences Comparison of Benzodiazepines Moosmann B Hutter M Huppertz LM Auwarter V Characterization of the designer benzodiazepines pyrazolam and flubromazepam and study on their detectability in human serum and urine samples PDF Archived from the original PDF on 2014 11 05 Retrieved 2014 11 05 a b Romazicon 2 flumazenil 3 Injection PDF Genentech Inc a b Flumazenil Injection 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Evolving Clinical and Adverse Effects Neurol Int 2022 Aug 22 14 3 648 663 doi 10 3390 neurolint14030053 PMID 35997362 Yu X Greenblatt HK Greenblatt DJ Designer benzodiazepines an update Expert Rev Clin Pharmacol 2023 Feb 16 2 109 117 doi 10 1080 17512433 2023 2170349 PMID 36649662 Haefely W Kyburz E Gerecke M Mohler H 1985 Recent advances in the molecular pharmacology of benzodiazepine receptors and in the structure activity relationships of their agonists and antagonists Adv Drug Res 1985 14 165 322 Winkler DA Burden FR Watkins AJ January 1998 Atomistic Topological Indices Applied to Benzodiazepines using Various Regression Methods Quantitative Structure Activity Relationships 17 1 14 19 doi 10 1002 SICI 1521 3838 199801 17 01 lt 14 AID QSAR14 gt 3 0 CO 2 U Thakur A Thakur M Khadikar P November 2003 Topological modeling of benzodiazepine receptor binding Bioorganic amp Medicinal Chemistry 11 23 5203 5207 doi 10 1016 j bmc 2003 08 014 PMID 14604684 So SS Karplus M December 1996 Genetic neural networks for quantitative structure activity relationships improvements and application of benzodiazepine affinity for benzodiazepine GABAA receptors Journal of Medicinal Chemistry 39 26 5246 5256 doi 10 1021 jm960536o PMID 8978853 Braestrup C Nielsen M 1983 Benzodiazepine receptors Biochemical Studies of CNS Receptors In Iversen LL Iversen SD Snyder SH eds Handbook of Psychopharmacology Springer ISBN 9781468443615 Zhang W Diaz Arauzo H Allen MS Koehler KF Cook JM 1996 Chapter 7 Chemical and computer assisted development of the inclusive pharmacophore of benzodiazepine receptors In Choudhary MI ed Studies in Medicinal Chemistry CRC Press p 303 ISBN 9783718658794 Obradovic AL Joksimovic S Poe MM Ramerstorfer J Varagic Z Namjoshi O et al March 2014 Sh I 048A an in vitro non selective super agonist at the benzodiazepine site of GABAA receptors the approximated activation of receptor subtypes may explain behavioral effects Brain Research 1554 36 48 doi 10 1016 j brainres 2014 01 036 PMC 3996760 PMID 24472579 Cornett EM Novitch MB Brunk AJ Davidson KS Menard BL Urman RD Kaye AD June 2018 New benzodiazepines for sedation Best Practice amp Research Clinical Anaesthesiology 32 2 149 164 doi 10 1016 j bpa 2018 06 007 PMID 30322456 S2CID 53501694 Clayton T Poe MM Rallapalli S Biawat P Savic MM Rowlett JK et al 2015 A Review of the Updated Pharmacophore for the Alpha 5 GABA A Benzodiazepine Receptor Model International Journal of Medicinal Chemistry 2015 430248 doi 10 1155 2015 430248 PMC 4657098 PMID 26682068 Moosmann B King LA Auwarter V June 2015 Designer benzodiazepines A new challenge World Psychiatry 14 2 248 doi 10 1002 wps 20236 PMC 4471986 PMID 26043347 Moosmann B Auwarter V 2018 Designer Benzodiazepines Another Class of New Psychoactive Substances In Maurer H Brandt S eds New Psychoactive Substances Handbook of Experimental Pharmacology Vol 252 pp 383 410 doi 10 1007 164 2018 154 ISBN 978 3 030 10560 0 PMID 30367253 Manchester KR Lomas EC Waters L Dempsey FC Maskell PD January 2018 The emergence of new psychoactive substance NPS benzodiazepines A review Drug Testing and Analysis 10 1 37 53 doi 10 1002 dta 2211 PMID 28471096 Waters L Manchester KR Maskell PD Haegeman C Haider S May 2018 The use of a quantitative structure activity relationship QSAR model to predict GABA A receptor binding of newly emerging benzodiazepines Science amp Justice 58 3 219 225 doi 10 1016 j scijus 2017 12 004 PMID 29685303 Zawilska JB Wojcieszak J July 2019 An expanding world of new psychoactive substances designer benzodiazepines Neurotoxicology 73 8 16 doi 10 1016 j neuro 2019 02 015 PMID 30802466 S2CID 73461430 Blair T Webb GA September 1977 Electronic factors in the structure activity relationship of some 1 4 benzodiazepin 2 ones Journal of Medicinal Chemistry 20 9 1206 1210 doi 10 1021 jm00219a019 PMID 926122 Biagi GL Barbaro AM Guerra MC Babbini M Gaiardi M Bartoletti M Borea PA February 1980 Rm values and structure activity relationship of benzodiazepines Journal of Medicinal Chemistry 23 2 193 201 doi 10 1021 jm00176a016 PMID 7359533 Catalani V Floresta G Botha M Corkery JM Guirguis A Vento A Abbate V Schifano F In silico studies on recreational drugs 3D quantitative structure activity relationship prediction of classified and de novo designer benzodiazepines Chem Biol Drug Des 2023 Jan 101 1 40 51 doi 10 1111 cbdd 14119 PMID 35838189 Spencer J Rathnam RP Chowdhry BZ September 2010 1 4 Benzodiazepin 2 ones in medicinal chemistry Future Medicinal Chemistry 2 9 1441 1449 doi 10 4155 fmc 10 226 PMID 21426139 Further reading editGitlow S 1 October 2006 Substance Use Disorders A Practical Guide 2nd ed USA Lippincott Williams and Wilkins p 110 ISBN 978 0 7817 6998 3 Galanter M Kleber HD 1 July 2008 The American Psychiatric Publishing Textbook of Substance Abuse Treatment 4th ed United States of America American Psychiatric Publishing Inc p 216 ISBN 978 1 58562 276 4 Retrieved from https en wikipedia org w index php title List of 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