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Clopenthixol

May 04, 2023

Clopenthixol (Sordinol), also known as clopentixol, is a typical antipsychotic drug of the thioxanthene class. It was introduced by Lundbeck in 1961.[1]

Clopenthixol
Clinical data
Routes of
administration		Oral
ATC code
Identifiers
  • (E,Z)-2-[4-[3-(2-chlorothioxanthen-9-ylidene) propyl]piperazin-1-yl]ethanol
CAS Number
  • 982-24-1 Y
  • E: 53772-84-2 Y
PubChem CID
  • 12454
ChemSpider
  • 11945 N
UNII
  • 0A432D932A
  • E: FLE878A8ZI Y
KEGG
  • D02613 N
ChEMBL
  • ChEMBL53904 N
CompTox Dashboard (EPA)
  • DTXSID9048223
ECHA InfoCard100.012.333
Chemical and physical data
FormulaC22H25ClN2OS
Molar mass400.97 g·mol−1
3D model (JSmol)
  • Interactive image
  • Clc2cc1C(c3c(Sc1cc2)cccc3)=CCCN4CCN(CCO)CC4
 NY (what is this?)  (verify)

Clopenthixol is a mixture of cis and trans isomers. Zuclopenthixol, the pure cis isomer, was later introduced by Lundbeck in 1962,[2] and has been much more widely used. Both drugs are equally effective as antipsychotics and have similar adverse effect profiles, but clopenthixol is half as active on a milligram-to-milligram basis and appears to produce more sedation in comparison.[3]

Clopenthixol is not approved for use in the United States.

Pharmacokinetics of long-acting injectable antipsychotics
Medication Brand name Class Vehicle Dosage Tmax t1/2 single t1/2 multiple logPc Ref
Aripiprazole lauroxil Aristada Atypical Watera 441–1064 mg/4–8 weeks 24–35 days ? 54–57 days 7.9–10.0
Aripiprazole monohydrate Abilify Maintena Atypical Watera 300–400 mg/4 weeks 7 days ? 30–47 days 4.9–5.2
Bromperidol decanoate Impromen Decanoas Typical Sesame oil 40–300 mg/4 weeks 3–9 days ? 21–25 days 7.9 [4]
Clopentixol decanoate Sordinol Depot Typical Viscoleob 50–600 mg/1–4 weeks 4–7 days ? 19 days 9.0 [5]
Flupentixol decanoate Depixol Typical Viscoleob 10–200 mg/2–4 weeks 4–10 days 8 days 17 days 7.2–9.2 [5][6]
Fluphenazine decanoate Prolixin Decanoate Typical Sesame oil 12.5–100 mg/2–5 weeks 1–2 days 1–10 days 14–100 days 7.2–9.0 [7][8][9]
Fluphenazine enanthate Prolixin Enanthate Typical Sesame oil 12.5–100 mg/1–4 weeks 2–3 days 4 days ? 6.4–7.4 [8]
Fluspirilene Imap, Redeptin Typical Watera 2–12 mg/1 week 1–8 days 7 days ? 5.2–5.8 [10]
Haloperidol decanoate Haldol Decanoate Typical Sesame oil 20–400 mg/2–4 weeks 3–9 days 18–21 days 7.2–7.9 [11][12]
Olanzapine pamoate Zyprexa Relprevv Atypical Watera 150–405 mg/2–4 weeks 7 days ? 30 days –
Oxyprothepin decanoate Meclopin Typical ? ? ? ? ? 8.5–8.7
Paliperidone palmitate Invega Sustenna Atypical Watera 39–819 mg/4–12 weeks 13–33 days 25–139 days ? 8.1–10.1
Perphenazine decanoate Trilafon Dekanoat Typical Sesame oil 50–200 mg/2–4 weeks ? ? 27 days 8.9
Perphenazine enanthate Trilafon Enanthate Typical Sesame oil 25–200 mg/2 weeks 2–3 days ? 4–7 days 6.4–7.2 [13]
Pipotiazine palmitate Piportil Longum Typical Viscoleob 25–400 mg/4 weeks 9–10 days ? 14–21 days 8.5–11.6 [6]
Pipotiazine undecylenate Piportil Medium Typical Sesame oil 100–200 mg/2 weeks ? ? ? 8.4
Risperidone Risperdal Consta Atypical Microspheres 12.5–75 mg/2 weeks 21 days ? 3–6 days –
Zuclopentixol acetate Clopixol Acuphase Typical Viscoleob 50–200 mg/1–3 days 1–2 days 1–2 days 4.7–4.9
Zuclopentixol decanoate Clopixol Depot Typical Viscoleob 50–800 mg/2–4 weeks 4–9 days ? 11–21 days 7.5–9.0
Note: All by intramuscular injection. Footnotes: a = Microcrystalline or nanocrystalline aqueous suspension. b = Low-viscosity vegetable oil (specifically fractionated coconut oil with medium-chain triglycerides). c = Predicted, from PubChem and DrugBank. Sources: Main: See template.

See also

References

  1. ^ Sneader, Walter (2005). Drug discovery: a history. New York: Wiley. p. 410. ISBN 0-471-89980-1.
  2. ^ José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. p. 516. ISBN 978-3-527-31058-6.
  3. ^ Gravem A, Engstrand E, Guleng RJ (November 1978). "Cis(Z)-clopenthixol and clopenthixol (Sordinol) in chronic psychotic patients. A double-blind clinical investigation". Acta Psychiatr Scand. 58 (5): 384–8. doi:10.1111/j.1600-0447.1978.tb03570.x. PMID 362830. S2CID 44833311.
  4. ^ Parent M, Toussaint C, Gilson H (1983). "Long-term treatment of chronic psychotics with bromperidol decanoate: clinical and pharmacokinetic evaluation". Current Therapeutic Research. 34 (1): 1–6.
  5. ^ a b Jørgensen A, Overø KF (1980). "Clopenthixol and flupenthixol depot preparations in outpatient schizophrenics. III. Serum levels". Acta Psychiatrica Scandinavica. Supplementum. 279: 41–54. doi:10.1111/j.1600-0447.1980.tb07082.x. PMID 6931472.
  6. ^ a b Reynolds JE (1993). "Anxiolytic sedatives, hypnotics and neuroleptics.". Martindale: The Extra Pharmacopoeia (30th ed.). London: Pharmaceutical Press. pp. 364–623.
  7. ^ Ereshefsky L, Saklad SR, Jann MW, Davis CM, Richards A, Seidel DR (May 1984). "Future of depot neuroleptic therapy: pharmacokinetic and pharmacodynamic approaches". The Journal of Clinical Psychiatry. 45 (5 Pt 2): 50–9. PMID 6143748.
  8. ^ a b Curry SH, Whelpton R, de Schepper PJ, Vranckx S, Schiff AA (April 1979). "Kinetics of fluphenazine after fluphenazine dihydrochloride, enanthate and decanoate administration to man". British Journal of Clinical Pharmacology. 7 (4): 325–31. doi:10.1111/j.1365-2125.1979.tb00941.x. PMC 1429660. PMID 444352.
  9. ^ Young D, Ereshefsky L, Saklad SR, Jann MW, Garcia N (1984). Explaining the pharmacokinetics of fluphenazine through computer simulations. (Abstract.). 19th Annual Midyear Clinical Meeting of the American Society of Hospital Pharmacists. Dallas, Texas.
  10. ^ Janssen PA, Niemegeers CJ, Schellekens KH, Lenaerts FM, Verbruggen FJ, van Nueten JM, et al. (November 1970). "The pharmacology of fluspirilene (R 6218), a potent, long-acting and injectable neuroleptic drug". Arzneimittel-Forschung. 20 (11): 1689–98. PMID 4992598.
  11. ^ Beresford R, Ward A (January 1987). "Haloperidol decanoate. A preliminary review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in psychosis". Drugs. 33 (1): 31–49. doi:10.2165/00003495-198733010-00002. PMID 3545764.
  12. ^ Reyntigens AJ, Heykants JJ, Woestenborghs RJ, Gelders YG, Aerts TJ (1982). "Pharmacokinetics of haloperidol decanoate. A 2-year follow-up". International Pharmacopsychiatry. 17 (4): 238–46. doi:10.1159/000468580. PMID 7185768.
  13. ^ Larsson M, Axelsson R, Forsman A (1984). "On the pharmacokinetics of perphenazine: a clinical study of perphenazine enanthate and decanoate". Current Therapeutic Research. 36 (6): 1071–88.

External links


 

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May 04, 2023
clopenthixol, sordinol, also, known, clopentixol, typical, antipsychotic, drug, thioxanthene, class, introduced, lundbeck, 1961, clinical, dataroutes, ofadministrationoralatc, coden05af02, identifiersiupac, name, chlorothioxanthen, ylidene, propyl, piperazin, . Clopenthixol Sordinol also known as clopentixol is a typical antipsychotic drug of the thioxanthene class It was introduced by Lundbeck in 1961 1 ClopenthixolClinical dataRoutes ofadministrationOralATC codeN05AF02 WHO IdentifiersIUPAC name E Z 2 4 3 2 chlorothioxanthen 9 ylidene propyl piperazin 1 yl ethanolCAS Number982 24 1 YE 53772 84 2 YPubChem CID12454ChemSpider11945 NUNII0A432D932AE FLE878A8ZI YKEGGD02613 NChEMBLChEMBL53904 NCompTox Dashboard EPA DTXSID9048223ECHA InfoCard100 012 333Chemical and physical dataFormulaC 22H 25Cl N 2O SMolar mass400 97 g mol 13D model JSmol Interactive imageSMILES Clc2cc1C c3c Sc1cc2 cccc3 CCCN4CCN CCO CC4 N Y what is this verify Clopenthixol is a mixture of cis and trans isomers Zuclopenthixol the pure cis isomer was later introduced by Lundbeck in 1962 2 and has been much more widely used Both drugs are equally effective as antipsychotics and have similar adverse effect profiles but clopenthixol is half as active on a milligram to milligram basis and appears to produce more sedation in comparison 3 Clopenthixol is not approved for use in the United States vte Pharmacokinetics of long acting injectable antipsychotics Medication Brand name Class Vehicle Dosage Tmax t1 2 single t1 2 multiple logPc RefAripiprazole lauroxil Aristada Atypical Watera 441 1064 mg 4 8 weeks 24 35 days 54 57 days 7 9 10 0Aripiprazole monohydrate Abilify Maintena Atypical Watera 300 400 mg 4 weeks 7 days 30 47 days 4 9 5 2Bromperidol decanoate Impromen Decanoas Typical Sesame oil 40 300 mg 4 weeks 3 9 days 21 25 days 7 9 4 Clopentixol decanoate Sordinol Depot Typical Viscoleob 50 600 mg 1 4 weeks 4 7 days 19 days 9 0 5 Flupentixol decanoate Depixol Typical Viscoleob 10 200 mg 2 4 weeks 4 10 days 8 days 17 days 7 2 9 2 5 6 Fluphenazine decanoate Prolixin Decanoate Typical Sesame oil 12 5 100 mg 2 5 weeks 1 2 days 1 10 days 14 100 days 7 2 9 0 7 8 9 Fluphenazine enanthate Prolixin Enanthate Typical Sesame oil 12 5 100 mg 1 4 weeks 2 3 days 4 days 6 4 7 4 8 Fluspirilene Imap Redeptin Typical Watera 2 12 mg 1 week 1 8 days 7 days 5 2 5 8 10 Haloperidol decanoate Haldol Decanoate Typical Sesame oil 20 400 mg 2 4 weeks 3 9 days 18 21 days 7 2 7 9 11 12 Olanzapine pamoate Zyprexa Relprevv Atypical Watera 150 405 mg 2 4 weeks 7 days 30 days Oxyprothepin decanoate Meclopin Typical 8 5 8 7Paliperidone palmitate Invega Sustenna Atypical Watera 39 819 mg 4 12 weeks 13 33 days 25 139 days 8 1 10 1Perphenazine decanoate Trilafon Dekanoat Typical Sesame oil 50 200 mg 2 4 weeks 27 days 8 9Perphenazine enanthate Trilafon Enanthate Typical Sesame oil 25 200 mg 2 weeks 2 3 days 4 7 days 6 4 7 2 13 Pipotiazine palmitate Piportil Longum Typical Viscoleob 25 400 mg 4 weeks 9 10 days 14 21 days 8 5 11 6 6 Pipotiazine undecylenate Piportil Medium Typical Sesame oil 100 200 mg 2 weeks 8 4Risperidone Risperdal Consta Atypical Microspheres 12 5 75 mg 2 weeks 21 days 3 6 days Zuclopentixol acetate Clopixol Acuphase Typical Viscoleob 50 200 mg 1 3 days 1 2 days 1 2 days 4 7 4 9Zuclopentixol decanoate Clopixol Depot Typical Viscoleob 50 800 mg 2 4 weeks 4 9 days 11 21 days 7 5 9 0Note All by intramuscular injection Footnotes a Microcrystalline or nanocrystalline aqueous suspension b Low viscosity vegetable oil specifically fractionated coconut oil with medium chain triglycerides c Predicted from PubChem and DrugBank Sources Main See template See also EditTypical antipsychotic ThioxantheneReferences Edit Sneader Walter 2005 Drug discovery a history New York Wiley p 410 ISBN 0 471 89980 1 Jose Miguel Vela Helmut Buschmann Jorg Holenz Antonio Parraga Antoni Torrens 2007 Antidepressants Antipsychotics Anxiolytics From Chemistry and Pharmacology to Clinical Application Weinheim Wiley VCH p 516 ISBN 978 3 527 31058 6 Gravem A Engstrand E Guleng RJ November 1978 Cis Z clopenthixol and clopenthixol Sordinol in chronic psychotic patients A double blind clinical investigation Acta Psychiatr Scand 58 5 384 8 doi 10 1111 j 1600 0447 1978 tb03570 x PMID 362830 S2CID 44833311 Parent M Toussaint C Gilson H 1983 Long term treatment of chronic psychotics with bromperidol decanoate clinical and pharmacokinetic evaluation Current Therapeutic Research 34 1 1 6 a b Jorgensen A Overo KF 1980 Clopenthixol and flupenthixol depot preparations in outpatient schizophrenics III Serum levels Acta Psychiatrica Scandinavica Supplementum 279 41 54 doi 10 1111 j 1600 0447 1980 tb07082 x PMID 6931472 a b Reynolds JE 1993 Anxiolytic sedatives hypnotics and neuroleptics Martindale The Extra Pharmacopoeia 30th ed London Pharmaceutical Press pp 364 623 Ereshefsky L Saklad SR Jann MW Davis CM Richards A Seidel DR May 1984 Future of depot neuroleptic therapy pharmacokinetic and pharmacodynamic approaches The Journal of Clinical Psychiatry 45 5 Pt 2 50 9 PMID 6143748 a b Curry SH Whelpton R de Schepper PJ Vranckx S Schiff AA April 1979 Kinetics of fluphenazine after fluphenazine dihydrochloride enanthate and decanoate administration to man British Journal of Clinical Pharmacology 7 4 325 31 doi 10 1111 j 1365 2125 1979 tb00941 x PMC 1429660 PMID 444352 Young D Ereshefsky L Saklad SR Jann MW Garcia N 1984 Explaining the pharmacokinetics of fluphenazine through computer simulations Abstract 19th Annual Midyear Clinical Meeting of the American Society of Hospital Pharmacists Dallas Texas Janssen PA Niemegeers CJ Schellekens KH Lenaerts FM Verbruggen FJ van Nueten JM et al November 1970 The pharmacology of fluspirilene R 6218 a potent long acting and injectable neuroleptic drug Arzneimittel Forschung 20 11 1689 98 PMID 4992598 Beresford R Ward A January 1987 Haloperidol decanoate A preliminary review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in psychosis Drugs 33 1 31 49 doi 10 2165 00003495 198733010 00002 PMID 3545764 Reyntigens AJ Heykants JJ Woestenborghs RJ Gelders YG Aerts TJ 1982 Pharmacokinetics of haloperidol decanoate A 2 year follow up International Pharmacopsychiatry 17 4 238 46 doi 10 1159 000468580 PMID 7185768 Larsson M Axelsson R Forsman A 1984 On the pharmacokinetics of perphenazine a clinical study of perphenazine enanthate and decanoate Current Therapeutic Research 36 6 1071 88 External links EditClopenthixol at the U S National Library of Medicine Medical Subject Headings MeSH This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Clopenthixol amp oldid 1126642626, wikipedia, wiki, book, books, library,

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