Benztropine

Benztropine

File:Benztropine.jpg
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 Y
ATC code	N04AC01
PubChem	CID 1201549
DrugBank	DB00245
ChemSpider	16736541 Y
UNII	1NHL2J4X8K Y
ChEBI	CHEBI:3048 Y
ChEMBL	CHEMBL1201203 N
Chemical data
Formula	C21H25NO
Mol. mass	307.429 g/mol
SMILES	eMolecules & PubChem
InChI 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
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.

Indications

Benztropine is an anticholinergic drug used in patients to reduce the side effects of antipsychotic treatment, such as pseudoparkinsonism and dystonia. Benztropine is also a second-line drug for the treatment of Parkinson's disease. It improves tremor but not rigidity and bradykinesia. Benztropine 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:

• Dry mouth
• Blurred vision
• Cognitive changes
• Constipation
• Urinary retention
• Tachycardia
• Anorexia
• Psychosis (in overdose)

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

Pharmacology

Benztropine 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 benztropine 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. Benztropine antagonises the effect of acetylcholine, decreasing the imbalance between the neurotransmitters acetylcholine and dopamine, which may improve the symptoms of early Parkinson's disease.

Benztropine does also act as FIASMA (functional inhibitor of acid sphingomyelinase).

Chemistry

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

• R.F. Phillips, N.J. Westfield, U.S. Patent 2,595,405 (1952).