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Benzatropine

January 07, 2023

Benzatropine (INN[1]), known as benztropine in the United States and Japan,[2] is a medication used to treat movement disorders like parkinsonism and dystonia, as well as extrapyramidal side effects of antipsychotics, including akathisia.[3] It is not useful for tardive dyskinesia.[3] It is taken by mouth or by injection into a vein or muscle.[3] Benefits are seen within two hours and last for up to ten hours.[4][5]

Benzatropine
Clinical data
Trade namesCogentin, others
Other namesbenzatropine (BAN UK), benztropine (USAN US)
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth, IM, IV
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Elimination half-life12-24 hours
ExcretionUrine
Identifiers
  • (3-endo)-3-(Diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane
CAS Number
  • 86-13-5 Y
PubChem CID
  • 1201549
IUPHAR/BPS
  • 7601
DrugBank
  • DB00245 N
ChemSpider
  • 16736541 Y
UNII
  • 1NHL2J4X8K
ChEBI
  • CHEBI:3048 Y
ChEMBL
  • ChEMBL1201203 N
CompTox Dashboard (EPA)
  • DTXSID9022659
Chemical and physical data
FormulaC21H25NO
Molar mass307.437 g·mol−1
3D model (JSmol)
  • Interactive image
  • CN4[C@@H]1CC[C@H]4C[C@H](C1)OC(c2ccccc2)c3ccccc3
  • InChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19+,20+ Y
  • Key:GIJXKZJWITVLHI-PMOLBWCYSA-N Y
 NY (what is this?)  (verify)

Common side effects include dry mouth, blurry vision, nausea, and constipation.[3] Serious side effect may include urinary retention, hallucinations, hyperthermia, and poor coordination.[3] It is unclear if use during pregnancy or breastfeeding is safe.[6] Benzatropine is an anticholinergic which works by blocking the activity of the muscarinic acetylcholine receptor.[3]

Benzatropine was approved for medical use in the United States in 1954.[3] It is available as a generic medication.[3] In 2020, it was the 229th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[7][8] It is sold under the brand name Cogentin among others.[3]

Medical uses

Benzatropine is used to reduce extrapyramidal side effects of antipsychotic treatment. Benzatropine is also a second-line drug for the treatment of Parkinson's disease. It improves tremor, and may alleviate rigidity and bradykinesia.[9] Benzatropine is also sometimes used for the treatment of dystonia, a rare disorder that causes abnormal muscle contraction, resulting in twisting postures of limbs, trunk, or face.

Adverse effects

These are principally anticholinergic:

While some studies suggest that use of anticholinergics increases the risk of tardive dyskinesia (a long-term side effect of antipsychotics),[10][11] other studies have found no association between anticholinergic exposure and risk of developing tardive dyskinesia,[12] although symptoms may be worsened.[13]

Drugs that decrease cholinergic transmission may impair storage of new information into long-term memory. Anticholinergic agents can also impair time perception.[14]

Pharmacology

Benzatropine is a centrally acting anticholinergic/antihistamine agent. It is a selective M1 muscarinic acetylcholine receptor antagonist. Benzatropine partially blocks cholinergic activity in the basal ganglia and has also been shown to increase the availability of dopamine by blocking its reuptake and storage in central sites, and as a result, increasing dopaminergic activity. Animal studies have indicated that anticholinergic activity of benzatropine is approximately one-half that of atropine, while its antihistamine activity approaches that of mepyramine. Its anticholinergic effects have been established as therapeutically significant in the management of Parkinsonism. Benzatropine antagonizes the effect of acetylcholine, decreasing the imbalance between the neurotransmitters acetylcholine and dopamine, which may improve the symptoms of early Parkinson's disease.[15]

Benzatropine analogues are atypical dopamine reuptake inhibitors,[16] which might make them useful for people with akathisia secondary to antipsychotic therapy.[17]

Benzatropine also acts as a functional inhibitor of acid sphingomyelinase (FIASMA).[18]

Benzatropine has been also identified, by a high throughput screening approach, as a potent differentiating agent for oligodendrocytes, possibly working through M1 and M3 muscarinic receptors. In preclinical models for multiple sclerosis, benzatropine decreased clinical symptoms and enhanced re-myelination.[19]

Other animals

In veterinary medicine, benzatropine is used to treat priapism in stallions.[20]

Naming

Since 1959, benzatropine is the official international nonproprietary name of the medication under the INN scheme, the medication naming system coordinated by the World Health Organization; it is also the British Approved Name (BAN) given in the British Pharmacopoeia,[1][2] and has been the official nonproprietary name in Australia since 2015.[21] Regional variations of the "a" spelling are also used in French, Italian, Portuguese, and Spanish, as well as Latin (all medications are assigned a Latin name by WHO).[2]

"Benztropine" is the official United States Adopted Name (USAN), the medication naming system coordinated by the USAN Council, co-sponsored by the American Medical Association (AMA), the United States Pharmacopeial Convention (USP), and the American Pharmacists Association (APhA). It is also the Japanese Accepted Name (JAN)[22] and was used in Australia until 2015, when it was harmonized with the INN.[21]

Both names may be modified to account for the methanesulfonate salt as which the medication is formulated: the modified INN (INNm) and BAN (BANM) is benzatropine mesilate, while the modified USAN is benztropine mesylate.[23] The modified JAN is a hybrid form, benztropine mesilate.[22]

The misspelling benzotropine is also occasionally seen in the literature.

See also

References

  1. ^ a b World Health Organization (December 1959). "International Non-Proprietary Names for Pharmaceutical Preparations). Recommended International Non-Proprietary Names (Rec. I.N.N.): List 3º" (PDF). WHO Chronicle. 13 (12): 464. Retrieved 2020-12-01.
  2. ^ a b c World Health Organization. "INN: Benzatropine". WHO MedNet. Retrieved 2020-12-01.
  3. ^ a b c d e f g h i "Benztropine Mesylate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 9 April 2019.
  4. ^ Pagliaro LA, Pagliaro AM (1999). PNDR, Psychologists' Neuropsychotropic Drug Reference. Psychology Press. p. 47. ISBN 9780876309568.
  5. ^ Aschenbrenner DS, Venable SJ (2009). Drug Therapy in Nursing. Lippincott Williams & Wilkins. p. 197. ISBN 9780781765879.
  6. ^ "Benztropine (Cogentin) Use During Pregnancy". Drugs.com. Retrieved 9 April 2019.
  7. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  8. ^ "Benztropine - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  9. ^ DiMascio A, Bernardo DL, Greenblatt DJ, Marder JE (May 1976). "A controlled trial of amantadine in drug-induced extrapyramidal disorders". Archives of General Psychiatry. 33 (5): 599–602. doi:10.1001/archpsyc.1976.01770050055008. PMID 5066.
  10. ^ Kane JM, Smith JM (April 1982). "Tardive dyskinesia: prevalence and risk factors, 1959 to 1979". Archives of General Psychiatry. 39 (4): 473–481. doi:10.1001/archpsyc.1982.04290040069010. PMID 6121548. S2CID 10194153.
  11. ^ Wszola BA, Newell KM, Sprague RL (August 2001). "Risk factors for tardive dyskinesia in a large population of youths and adults". Experimental and Clinical Psychopharmacology. 9 (3): 285–296. doi:10.1037/1064-1297.9.3.285. PMID 11534539.
  12. ^ van Harten PN, Hoek HW, Matroos GE, Koeter M, Kahn RS (April 1998). "Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curaçao Extrapyramidal Syndromes Study III". The American Journal of Psychiatry. 155 (4): 565–567. doi:10.1176/ajp.155.4.565. PMID 9546009.
  13. ^ Yassa R (September 1988). "Tardive dyskinesia and anticholinergic drugs. A critical review of the literature". L'Encéphale. 14 Spec No (Spec No): 233–239. PMID 3063514.
  14. ^ Gelenberg AJ, Van Putten T, Lavori PW, Wojcik JD, Falk WE, Marder S, et al. (June 1989). "Anticholinergic effects on memory: benztropine versus amantadine". Journal of Clinical Psychopharmacology. 9 (3): 180–185. doi:10.1097/00004714-198906000-00004. PMID 2661606. S2CID 27308127.
  15. ^ MIMS Australia Pty Ltd. MIMS.
  16. ^ Hiranita T, Kohut SJ, Soto PL, Tanda G, Kopajtic TA, Katz JL (January 2014). "Preclinical efficacy of N-substituted benztropine analogs as antagonists of methamphetamine self-administration in rats". The Journal of Pharmacology and Experimental Therapeutics. 348 (1): 174–191. doi:10.1124/jpet.113.208264. PMC 3868882. PMID 24194527.
  17. ^ Adler LA, Peselow E, Rosenthal M, Angrist B (1993). "A controlled comparison of the effects of propranolol, benztropine, and placebo on akathisia: an interim analysis". Psychopharmacology Bulletin. 29 (2): 283–286. PMID 8290678.
  18. ^ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, et al. (2011). "Identification of novel functional inhibitors of acid sphingomyelinase". PLOS ONE. 6 (8): e23852. Bibcode:2011PLoSO...623852K. doi:10.1371/journal.pone.0023852. PMC 3166082. PMID 21909365.
  19. ^ Deshmukh VA, Tardif V, Lyssiotis CA, Green CC, Kerman B, Kim HJ, et al. (October 2013). "A regenerative approach to the treatment of multiple sclerosis". Nature. 502 (7471): 327–332. Bibcode:2013Natur.502..327D. doi:10.1038/nature12647. PMC 4431622. PMID 24107995.
  20. ^ Wilson DV, Nickels FA, Williams MA (November 1991). "Pharmacologic treatment of priapism in two horses". Journal of the American Veterinary Medical Association. 199 (9): 1183–1184. PMID 1752772.
  21. ^ a b "Updating medicine ingredient names - list of affected ingredients". Therapeutic Goods Administration. 2015-11-23. Retrieved 2020-12-01.
  22. ^ a b Compound D00778 at KEGG Pathway Database.
  23. ^ Sweetman, Sean C., ed. (2009). "Antiparkinsonian Drugs". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 797. ISBN 978-0-85369-840-1.

External links

  • "Benzatropine". Drug Information Portal. U.S. National Library of Medicine.

January 07, 2023
benzatropine, known, benztropine, united, states, japan, medication, used, treat, movement, disorders, like, parkinsonism, dystonia, well, extrapyramidal, side, effects, antipsychotics, including, akathisia, useful, tardive, dyskinesia, taken, mouth, injection. Benzatropine INN 1 known as benztropine in the United States and Japan 2 is a medication used to treat movement disorders like parkinsonism and dystonia as well as extrapyramidal side effects of antipsychotics including akathisia 3 It is not useful for tardive dyskinesia 3 It is taken by mouth or by injection into a vein or muscle 3 Benefits are seen within two hours and last for up to ten hours 4 5 BenzatropineClinical dataTrade namesCogentin othersOther namesbenzatropine BAN UK benztropine USAN US AHFS Drugs comMonographLicense dataUS DailyMed BenztropinePregnancycategoryAU B2Routes ofadministrationBy mouth IM IVATC codeN04AC01 WHO Legal statusLegal statusUS onlyPharmacokinetic dataMetabolismLiverElimination half life12 24 hoursExcretionUrineIdentifiersIUPAC name 3 endo 3 Diphenylmethoxy 8 methyl 8 azabicyclo 3 2 1 octaneCAS Number86 13 5 YPubChem CID1201549IUPHAR BPS7601DrugBankDB00245 NChemSpider16736541 YUNII1NHL2J4X8KChEBICHEBI 3048 YChEMBLChEMBL1201203 NCompTox Dashboard EPA DTXSID9022659Chemical and physical dataFormulaC 21H 25N OMolar mass307 437 g mol 13D model JSmol Interactive imageSMILES CN4 C H 1CC C H 4C C H C1 OC c2ccccc2 c3ccccc3InChI InChI 1S C21H25NO c1 22 18 12 13 19 22 15 20 14 18 23 21 16 8 4 2 5 9 16 17 10 6 3 7 11 17 h2 11 18 21H 12 15H2 1H3 t18 19 20 YKey GIJXKZJWITVLHI PMOLBWCYSA N Y N Y what is this verify Common side effects include dry mouth blurry vision nausea and constipation 3 Serious side effect may include urinary retention hallucinations hyperthermia and poor coordination 3 It is unclear if use during pregnancy or breastfeeding is safe 6 Benzatropine is an anticholinergic which works by blocking the activity of the muscarinic acetylcholine receptor 3 Benzatropine was approved for medical use in the United States in 1954 3 It is available as a generic medication 3 In 2020 it was the 229th most commonly prescribed medication in the United States with more than 2 million prescriptions 7 8 It is sold under the brand name Cogentin among others 3 Contents 1 Medical uses 2 Adverse effects 3 Pharmacology 4 Other animals 5 Naming 6 See also 7 References 8 External linksMedical uses EditBenzatropine is used to reduce extrapyramidal side effects of antipsychotic treatment Benzatropine is also a second line drug for the treatment of Parkinson s disease It improves tremor and may alleviate rigidity and bradykinesia 9 Benzatropine is also sometimes used for the treatment of dystonia a rare disorder that causes abnormal muscle contraction resulting in twisting postures of limbs trunk or face Adverse effects EditThese are principally anticholinergic Dry mouth Blurred vision Cognitive changes Drowsiness Constipation Urinary retention Tachycardia Anorexia Severe delirium and hallucinations in overdose While some studies suggest that use of anticholinergics increases the risk of tardive dyskinesia a long term side effect of antipsychotics 10 11 other studies have found no association between anticholinergic exposure and risk of developing tardive dyskinesia 12 although symptoms may be worsened 13 Drugs that decrease cholinergic transmission may impair storage of new information into long term memory Anticholinergic agents can also impair time perception 14 Pharmacology EditBenzatropine is a centrally acting anticholinergic antihistamine agent It is a selective M1 muscarinic acetylcholine receptor antagonist Benzatropine partially blocks cholinergic activity in the basal ganglia and has also been shown to increase the availability of dopamine by blocking its reuptake and storage in central sites and as a result increasing dopaminergic activity Animal studies have indicated that anticholinergic activity of benzatropine is approximately one half that of atropine while its antihistamine activity approaches that of mepyramine Its anticholinergic effects have been established as therapeutically significant in the management of Parkinsonism Benzatropine antagonizes the effect of acetylcholine decreasing the imbalance between the neurotransmitters acetylcholine and dopamine which may improve the symptoms of early Parkinson s disease 15 Benzatropine analogues are atypical dopamine reuptake inhibitors 16 which might make them useful for people with akathisia secondary to antipsychotic therapy 17 Benzatropine also acts as a functional inhibitor of acid sphingomyelinase FIASMA 18 Benzatropine has been also identified by a high throughput screening approach as a potent differentiating agent for oligodendrocytes possibly working through M1 and M3 muscarinic receptors In preclinical models for multiple sclerosis benzatropine decreased clinical symptoms and enhanced re myelination 19 Other animals EditIn veterinary medicine benzatropine is used to treat priapism in stallions 20 Naming EditSince 1959 benzatropine is the official international nonproprietary name of the medication under the INN scheme the medication naming system coordinated by the World Health Organization it is also the British Approved Name BAN given in the British Pharmacopoeia 1 2 and has been the official nonproprietary name in Australia since 2015 21 Regional variations of the a spelling are also used in French Italian Portuguese and Spanish as well as Latin all medications are assigned a Latin name by WHO 2 Benztropine is the official United States Adopted Name USAN the medication naming system coordinated by the USAN Council co sponsored by the American Medical Association AMA the United States Pharmacopeial Convention USP and the American Pharmacists Association APhA It is also the Japanese Accepted Name JAN 22 and was used in Australia until 2015 when it was harmonized with the INN 21 Both names may be modified to account for the methanesulfonate salt as which the medication is formulated the modified INN INNm and BAN BANM is benzatropine mesilate while the modified USAN is benztropine mesylate 23 The modified JAN is a hybrid form benztropine mesilate 22 The misspelling benzotropine is also occasionally seen in the literature See also EditGaboxadol Propantheline bromide Glycopyrrolate OxybutyninReferences Edit a b World Health Organization December 1959 International Non Proprietary Names for Pharmaceutical Preparations Recommended International Non Proprietary Names Rec I N N List 3º PDF WHO Chronicle 13 12 464 Retrieved 2020 12 01 a b c World Health Organization INN Benzatropine WHO MedNet Retrieved 2020 12 01 a b c d e f g h i Benztropine Mesylate Monograph for Professionals Drugs com American Society of Health System Pharmacists Retrieved 9 April 2019 Pagliaro LA Pagliaro AM 1999 PNDR Psychologists Neuropsychotropic Drug Reference Psychology Press p 47 ISBN 9780876309568 Aschenbrenner DS Venable SJ 2009 Drug Therapy in Nursing Lippincott Williams amp Wilkins p 197 ISBN 9780781765879 Benztropine Cogentin Use During Pregnancy Drugs com Retrieved 9 April 2019 The Top 300 of 2020 ClinCalc Retrieved 7 October 2022 Benztropine Drug Usage Statistics ClinCalc Retrieved 7 October 2022 DiMascio A Bernardo DL Greenblatt DJ Marder JE May 1976 A controlled trial of amantadine in drug induced extrapyramidal disorders Archives of General Psychiatry 33 5 599 602 doi 10 1001 archpsyc 1976 01770050055008 PMID 5066 Kane JM Smith JM April 1982 Tardive dyskinesia prevalence and risk factors 1959 to 1979 Archives of General Psychiatry 39 4 473 481 doi 10 1001 archpsyc 1982 04290040069010 PMID 6121548 S2CID 10194153 Wszola BA Newell KM Sprague RL August 2001 Risk factors for tardive dyskinesia in a large population of youths and adults Experimental and Clinical Psychopharmacology 9 3 285 296 doi 10 1037 1064 1297 9 3 285 PMID 11534539 van Harten PN Hoek HW Matroos GE Koeter M Kahn RS April 1998 Intermittent neuroleptic treatment and risk for tardive dyskinesia Curacao Extrapyramidal Syndromes Study III The American Journal of Psychiatry 155 4 565 567 doi 10 1176 ajp 155 4 565 PMID 9546009 Yassa R September 1988 Tardive dyskinesia and anticholinergic drugs A critical review of the literature L Encephale 14 Spec No Spec No 233 239 PMID 3063514 Gelenberg AJ Van Putten T Lavori PW Wojcik JD Falk WE Marder S et al June 1989 Anticholinergic effects on memory benztropine versus amantadine Journal of Clinical Psychopharmacology 9 3 180 185 doi 10 1097 00004714 198906000 00004 PMID 2661606 S2CID 27308127 MIMS Australia Pty Ltd MIMS Hiranita T Kohut SJ Soto PL Tanda G Kopajtic TA Katz JL January 2014 Preclinical efficacy of N substituted benztropine analogs as antagonists of methamphetamine self administration in rats The Journal of Pharmacology and Experimental Therapeutics 348 1 174 191 doi 10 1124 jpet 113 208264 PMC 3868882 PMID 24194527 Adler LA Peselow E Rosenthal M Angrist B 1993 A controlled comparison of the effects of propranolol benztropine and placebo on akathisia an interim analysis Psychopharmacology Bulletin 29 2 283 286 PMID 8290678 Kornhuber J Muehlbacher M Trapp S Pechmann S Friedl A Reichel M et al 2011 Identification of novel functional inhibitors of acid sphingomyelinase PLOS ONE 6 8 e23852 Bibcode 2011PLoSO 623852K doi 10 1371 journal pone 0023852 PMC 3166082 PMID 21909365 Deshmukh VA Tardif V Lyssiotis CA Green CC Kerman B Kim HJ et al October 2013 A regenerative approach to the treatment of multiple sclerosis Nature 502 7471 327 332 Bibcode 2013Natur 502 327D doi 10 1038 nature12647 PMC 4431622 PMID 24107995 Wilson DV Nickels FA Williams MA November 1991 Pharmacologic treatment of priapism in two horses Journal of the American Veterinary Medical Association 199 9 1183 1184 PMID 1752772 a b Updating medicine ingredient names list of affected ingredients Therapeutic Goods Administration 2015 11 23 Retrieved 2020 12 01 a b Compound D00778 at KEGG Pathway Database Sweetman Sean C ed 2009 Antiparkinsonian Drugs Martindale The Complete Drug Reference 36th ed London Pharmaceutical Press p 797 ISBN 978 0 85369 840 1 External links Edit Benzatropine Drug Information Portal U S National Library of Medicine Portal Medicine Retrieved from https en wikipedia org w index php title Benzatropine amp oldid 1121009483, wikipedia, wiki, book, books, library,

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