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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/03/22 23:39:23」(JST)

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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.

Medical uses[edit]

Benzatropine is an anticholinergic drug used in patients to reduce the side effects of antipsychotic treatment, such as parkinsonism 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[edit]

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),^[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[edit]

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 is also a dopamine reuptake inhibitor, which makes it useful for people with extrapyramidal symptoms who take antipsychotics.^{[citation needed]}

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

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 (Deshmukh et al., Nature 2013).

Chemistry[edit]

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

References[edit]

^ Kane JM, Smith JM (1982). "Tardive dyskinesia: Prevalence and risk factors, 1959 to 1979". Archives of General Psychiatry 39 (4): 473–81. PMID 6121548.
^ 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.
^ 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.
^ Yassa R (1988). "Tardive dyskinesia and anticholinergic drugs. A critical review of the literature". L'Encephale 14 (Spec No): 233–9. PMID 3063514.
^ MIMS Australia Pty Ltd. MIMS.
^ 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. PMC 3166082. PMID 21909365.
^ Phillips RF, Westfield NJ (1952) U.S. Patent 2,595,405

UpToDate Contents

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1. 統合失調症に対する薬物療法：急性期および維持期の治療 pharmacotherapy for schizophrenia acute and maintenance phase treatment
2. 統合失調症におけるうつ病 depression in schizophrenia
3. 第一世代（定型）抗精神病剤中毒 first generation typical antipsychotic medication poisoning
4. ミオクローヌスの治療 treatment of myoclonus
5. 遅発性ジスキネジア：予防および治療 tardive dyskinesia prevention and treatment

English Journal

Relationship between conformational changes in the dopamine transporter and cocaine-like subjective effects of uptake inhibitors.

Loland CJ1, Desai RI, Zou MF, Cao J, Grundt P, Gerstbrein K, Sitte HH, Newman AH, Katz JL, Gether U.
Molecular pharmacology.Mol Pharmacol.2008 Mar;73(3):813-23. Epub 2007 Oct 31.
Cocaine exerts its stimulatory effect by inhibiting the dopamine transporter (DAT). However, novel benztropine- and rimcazole-based inhibitors show reduced stimulant effects compared with cocaine, despite higher affinity and selectivity for DAT. To investigate possible mechanisms, we compared the su
PMID 17978168

The uptake inhibitors cocaine and benztropine differentially alter the conformation of the human dopamine transporter.

Reith ME1, Berfield JL, Wang LC, Ferrer JV, Javitch JA.
The Journal of biological chemistry.J Biol Chem.2001 Aug 3;276(31):29012-8. Epub 2001 Jun 6.
The binding affinity of the cocaine analog [(3)H]2 beta-carbomethoxy-3beta-(4-fluorophenyl) tropane (WIN) for the dopamine transporter (DAT) is increased by the reaction of Cys-90, at the extracellular end of the first transmembrane segment, with methanethiosulfonate (MTS) reagents. Cocaine enhances
PMID 11395483

Transdermal delivery of antiparkinsonian agent, benztropine. I. Effect of vehicles on skin permeation.

Gorukanti SR1, Li L, Kim KH.
International journal of pharmaceutics.Int J Pharm.1999 Dec 10;192(2):159-72.
The influence of pH and various lipophilic and hydrophilic vehicles on the epidermal permeation of benztropine (BZ) free base and its mesylate salt were studied in vitro using the hairless mouse (HLM) and human cadaver (HC) skin membranes. The pH-partition behavior of BZ base (pK(a)=10) was examined
PMID 10567747

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★リンクテーブル★

リンク元	「ベンズトロピン」「メシル酸ベンツトロピン」
関連記事	「mesilate」

「ベンズトロピン」

Benzatropine
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	℞-only (US)
Routes	Oral, IM, IV
Pharmacokinetic data
Metabolism	Hepatic
Half-life	12-24 hours
Excretion	Urine
Identifiers
CAS number	86-13-5
ATC code	N04AC01
PubChem	CID 1201549
DrugBank	DB00245
ChemSpider	16736541
UNII	1NHL2J4X8K
ChEBI	CHEBI:3048
ChEMBL	CHEMBL1201203
Synonyms	Benztropine
Chemical data
Formula	C21H25NO
Mol. mass	307.429 g/mol
	SMILES CN4[C@@H]1CC[C@H]4C[C@H](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 ;
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　　[★]

英: benztropine
化: メシル酸ベンズトロピン benztropine mesilate

抗コリン薬

「メシル酸ベンツトロピン」

　　[★]

英: benztropine mesilate
関: ベンズトロピン、メシル酸ベンズトロピン

「mesilate」

　　[★]

メシル酸、(化合物)シル酸塩、メタンスルホン酸塩

関: mesylate、methanesulfonate

[1] Kane JM, Smith JM (1982). "Tardive dyskinesia: Prevalence and risk factors, 1959 to 1979". Archives of General Psychiatry 39 (4): 473–81. PMID 6121548.

[pmid11534539-2] 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.

[pmid9546009-3] 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.

[pmid18504571-6] 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. PMC 3166082. PMID 21909365.

[7] Phillips RF, Westfield NJ (1952) U.S. Patent 2,595,405

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benztropine mesilate