Benzatropine

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Benzatropine
Systematic (IUPAC) name
(3-endo)-3-(Diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane
Clinical data
Trade namesCogentin
AHFS/Drugs.commonograph
Pregnancy cat.C (US)
Legal status-only (US)
RoutesOral, IM, IV
Identifiers
CAS number86-13-5 YesY
ATC codeN04AC01
PubChemCID 1201549
DrugBankDB00245
ChemSpider16736541 YesY
UNII1NHL2J4X8K YesY
ChEBICHEBI:3048 YesY
ChEMBLCHEMBL1201203 N
SynonymsBenztropine
Chemical data
FormulaC21H25NO 
Mol. mass307.429 g/mol
 N (what is this?)  (verify)
 
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Benzatropine
Systematic (IUPAC) name
(3-endo)-3-(Diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane
Clinical data
Trade namesCogentin
AHFS/Drugs.commonograph
Pregnancy cat.C (US)
Legal status-only (US)
RoutesOral, IM, IV
Identifiers
CAS number86-13-5 YesY
ATC codeN04AC01
PubChemCID 1201549
DrugBankDB00245
ChemSpider16736541 YesY
UNII1NHL2J4X8K YesY
ChEBICHEBI:3048 YesY
ChEMBLCHEMBL1201203 N
SynonymsBenztropine
Chemical data
FormulaC21H25NO 
Mol. mass307.429 g/mol
 N (what is this?)  (verify)

Benzatropine (INN), also known as benztropine (USAN, BAN), is an anticholinergic marketed under the trade name Cogentin which is used in the treatment of Parkinson's disease, Parkinsonism, and dystonia.

Contents

Medical uses

Benzatropine is an anticholinergic drug used in patients to reduce the side effects of antipsychotic treatment, such as pseudoparkinsonism and dystonia. Benzatropine is also a second-line drug for the treatment of Parkinson's disease. It improves tremor, but not rigidity and bradykinesia. 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),[1][2] other studies have found no association between anticholinergic exposure and risk of developing tardive dyskinesia,[3] although symptoms may be worsened.[4]

Pharmacology

Benzatropine is a centrally acting anticholinergic/antihistamine agent resulting from the combination of the tropine portion of the atropine molecule and the benzohydryl portion of diphenhydramine. 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.[5]

Benzatropine also acts as a functional inhibitor of acid sphingomyelinase (FIASMA).[6]

Chemistry

Benzatropine can be synthesized by the reaction of tropine and diphenyldiazomethane.[7]

Benztropine synthesis.png

References

  1. ^ Kane, J. M.; Smith, J. M. (1982). "Tardive dyskinesia: Prevalence and risk factors, 1959 to 1979". Archives of General Psychiatry 39 (4): 473–481. PMID 6121548.  edit
  2. ^ Wszola BA, Newell KM, Sprague RL (2001). "Risk factors for tardive dyskinesia in a large population of youths and adults". Experimental and clinical psychopharmacology 9 (3): 285–96. doi:10.1037/1064-1297.9.3.285. PMID 11534539. 
  3. ^ van Harten PN, Hoek HW, Matroos GE, Koeter M, Kahn RS (1998). "Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curaçao Extrapyramidal Syndromes Study III". The American Journal of Psychiatry 155 (4): 565–7. PMID 9546009. 
  4. ^ Yassa, R (1988). "Tardive dyskinesia and anticholinergic drugs. A critical review of the literature.". L'Encephale 14 Spec No: 233–9. PMID 3063514. 
  5. ^ MIMS Australia Pty Ltd. MIMS.
  6. ^ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P (2011). "Identification of novel functional inhibitors of acid sphingomyelinase". PLoS ONE 6 (8): e23852. doi:10.1371/journal.pone.0023852. 
  7. ^ R.F. Phillips, N.J. Westfield, U.S. Patent 2,595,405 (1952)