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Benzatropine

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Revision as of 08:08, 20 October 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Benztropine
File:Benztropine.png
Clinical data
Trade namesCogentin
AHFS/Drugs.comMonograph
Routes of
administration
Oral, IM, IV
ATC code
Identifiers
IUPAC name
  • (3-endo)-3-(diphenylmethoxy)-8-methyl-8-azabicyclooctane
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H25NO
Molar mass307.429 g/mol g·mol
3D model (JSmol)
SMILES
  • CN41CC4C(C1)OC(c2ccccc2)c3ccccc3
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+
  • Key:GIJXKZJWITVLHI-PMOLBWCYSA-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.

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), other studies have found no association between anticholinergic exposure and risk of developing tardive dyskinesia, although symptoms may be worsened.

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.

Chemistry

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

References

  1. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 6121548, please use {{cite journal}} with |pmid=6121548 instead.
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
Antiparkinson agents (N04)
Dopaminergics
DA precursors
DA receptor agonists
MAO-B inhibitors
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Anticholinergics
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Acetylcholine receptor modulators
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Nicotinic acetylcholine receptor modulators
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Nicotinic acetylcholine receptor modulators
nAChRsTooltip Nicotinic acetylcholine receptors
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