Benzatropine

Benztropine
Systematic (IUPAC) name
(3-endo)-3-(diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane
Clinical data
Trade names Cogentin
AHFS/Drugs.com monograph
Pregnancy cat. C(US)
Legal status  ?
Routes Oral, IM, IV
Identifiers
CAS number 86-13-5 YesY
ATC code N04AC01
PubChem CID 1201549
DrugBank DB00245
ChemSpider 16736541 YesY
UNII 1NHL2J4X8K YesY
ChEBI CHEBI:3048 YesY
ChEMBL CHEMBL1201203 N
Chemical data
Formula C21H25NO 
Mol. mass 307.429 g/mol
SMILES eMolecules & PubChem
 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, akathisia, and dystonia.

Contents

Indications

Benzatropine is used in patients to reduce the side effects of antipsychotic treatment, such as parkinsonism and akathisia. Benzatropine is also a second-line drug for the treatment of Parkinson's disease. It improves tremor and rigidity but not 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.

Side 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 antagonises the effect of acetylcholine, decreasing the imbalance between the neurotransmitters acetylcholine and dopamine, which may improve the symptoms of early Parkinson's disease.[5]

Chemistry

Benztropine, 3-(diphenylmethoxy)tropane, is synthesized by the reaction of tropine and diphenyldiazomethane.

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.