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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/09 12:33:32」(JST)

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Entacapone (INN) (/ˌɛntəkəˈpoʊn/ or /ɛnˈtækəpoʊn/) is a drug that functions as a catechol-O-methyl transferase (COMT) inhibitor. It is used in the treatment of Parkinson's disease.

When administered in conjunction with dopaminergic agents such as L-DOPA, entacapone prevents COMT from metabolizing L-DOPA into 3-methoxy-4-hydroxy-L-phenylalanine (3-OMD) in the periphery, which does not easily cross the blood–brain barrier (BBB). Pharmacologically, entacapone is somewhat similar to carbidopa or benserazide, in that it is an inhibitor of an enzyme that converts L-DOPA into a compound that cannot cross the blood–brain barrier. Carbidopa and benserazide inhibit aromatic L-amino acid decarboxylase, which converts L-DOPA into dopamine, which cannot cross the blood–brain barrier.

Entacapone is a member of the class of drugs known as nitrocatechols.

Side effects

The most frequent undesirable effects caused by entacapone relate to the increased effects of L-DOPA, such as involuntary movements (dyskinesias). These occur most frequently at the beginning of entacapone treatment. Others common side effects are gastrointestinal problems, including nausea and abdominal pains. Diarrhea is a frequently reported and troublesome side effect that can result in unnecessary investigation, but resolves quickly on withdrawal of the drug.^[1] Entacapone may cause urine to turn reddish-brown. This is a harmless side effect and is not a cause for concern. In studies with entacapone, some people have reported experiencing a dry mouth.

Products

Entacapone is developed by Orion Pharma and marketed by Novartis under the trade name COMTan in the United States.

Stalevo is another medication developed by Orion Pharma and marketed by Novartis that contains entacapone in combination with carbidopa and levodopa (active ingredients in Sinemet).

References

^ Singer C (2002). "Adverse effects in the treatment of Parkinson’s disease". Expert Review of Neurotherapeutics 2 (1): 105–118. doi:10.1586/14737175.2.1.105.

External links

Entacapone/Carbidopa/Levodopa (marketed as Stalevo) Information (FDA)
Entacapone (Medline plus/NIH)
Comtan (manufacturer's website)
Stalevo (manufacturer's website)

UpToDate Contents

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1. パーキンソン病の薬理学的治療 pharmacologic treatment of parkinson disease
2. パーキンソン病における症状の変動およびジスキネジア motor fluctuations and dyskinesia in parkinson disease
3. 周術期の投薬マネージメント perioperative medication management
4. 患者情報：パーキンソン病の治療選択肢・薬物療法（詳細） parkinson disease treatment options medications beyond the basics

English Journal

Synergistic inhibition of lung cancer cell lines by (-)-epigallocatechin-3-gallate in combination with clinically used nitrocatechol inhibitors of catechol-O-methyltransferase.

Forester SC, Lambert JD.SourceCenter of Excellence for Plant and Mushroom Foods for Human Health, Department of Food Science.
Carcinogenesis.Carcinogenesis.2013 Nov 26. [Epub ahead of print]
(-)-Epigallocatechin-3-gallate (EGCG) has exhibited been studied for lung cancer inhibitory activity in vitro and in animal models, but it is rapidly methylated and inactivated by catechol-O-methyltransferase (COMT). Entacapone and tolcapone, COMT inhibitors, are used to mitigate the symptoms of Par
PMID 24148818

Efficacy of levodopa/carbidopa/entacapone versus levodopa/carbidopa in patients with early Parkinson's disease experiencing mild wearing-off: a randomised, double-blind trial.

Tolosa E, Hernández B, Linazasoro G, López-Lozano JJ, Mir P, Marey J, Kulisevsky J.SourceNeurology Service, Centro de Investigación Biomédica en Red sobre Enfermedades Neurodegenerativas (CIBERNED), Hospital Clínic, IDIBAPS, Universitat de Barcelona, Barcelona, Spain, etolosa@clinic.ub.es.
Journal of neural transmission (Vienna, Austria : 1996).J Neural Transm.2013 Nov 20. [Epub ahead of print]
To compare the efficacy and safety of levodopa/carbidopa/entacapone (LCE) with levodopa/carbidopa (LC) on Parkinson's disease (PD) patients with mild, or only minimally disabling motor complications. A prospective 3-month, multicentre, parallel-group, double-blind, and randomised phase IV study was
PMID 24253234

Entacapone augmentation of antipsychotic treatment in schizophrenic patients with negative symptoms; a double-blind placebo-controlled study.

Kaphzan H, Ben-Shachar D, Klein E.SourceSagol Department of Neurobiology, University of Haifa, Haifa, Israel.
The international journal of neuropsychopharmacology / official scientific journal of the Collegium Internationale Neuropsychopharmacologicum (CINP).Int J Neuropsychopharmacol.2013 Nov 12:1-4. [Epub ahead of print]
Negative symptoms in schizophrenia are associated with decreased dopaminergic activity in the prefrontal cortex (PFC). It is hypothesized that increasing dopamine levels would alleviate negative symptoms. Termination of dopamine activity in the PFC is mainly via catechol-O-methyl tranferase (COMT) a
PMID 24229565

Japanese Journal

Usefulness of Monitoring Blood L-dopa and L-dopa Metabolite Concentrations in Patients with Advanced Parkinson's Disease Receiving COMT Inhibitor Entacapone Combination Therapy

応用薬理 85(1), 15-24, 2013-08-26
NAID 10031193108

Microbial β-glycosylation of entacapone by Cunninghamella echinulata ATCC 9245(MICROBIAL PHYSIOLOGY AND BIOTECHNOLOGY)

Journal of bioscience and bioengineering 113(5), 611-613, 2012-05
NAID 110009456901

Quantitative Prediction of Intestinal Glucuronidation of Drugs in Rats Using In Vitro Metabolic Clearance Data

Drug Metabolism and Pharmacokinetics 27(2), 171-180, 2012
NAID 130004463238

Related Pictures

Entacapone - FDA prescribing information, side effects and uses T1 100 Pill Images (Red / Elliptical / Oval) EN1 200 Pill - entacapone 200 mg Entacapone: Indications, Side Effects, Warnings - Drugs.com Pillbox - National Library of Medicine W784 Pill Images (Red / Elliptical / Oval) Entacapone User Reviews for Parkinson's Disease at Drugs.com Carbidopa, Levodopa and Entacapone | Sun Pharmaceutical Industries Ltd.

★リンクテーブル★

リンク元

「エンタカポン」

Entacapone
Systematic (IUPAC) name
	(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
Clinical data
Trade names	Comtan (single ingredient), Stalevo (multi-ingredient)
AHFS/Drugs.com	monograph
MedlinePlus	a601236
Licence data	US Daily Med:link
Pregnancy; category	AU: B3; US: C (Risk not ruled out);
Legal status	AU: Prescription Only (S4); CA: ℞-only; UK: Prescription-only (POM); US: ℞-only;
Routes of; administration	Oral
Pharmacokinetic data
Bioavailability	35%
Protein binding	98% (binds to serum albumin)
Metabolism	Hepatic
Biological half-life	0.4-0.7 hour
Excretion	Faeces (90%), Urine (10%)
Identifiers
CAS Registry Number	130929-57-6
ATC code	N04BX02
PubChem	CID: 5281081
IUPHAR/BPS	6647
DrugBank	DB00494
ChemSpider	4444537
UNII	4975G9NM6T
KEGG	D00781
ChEBI	CHEBI:4798
ChEMBL	CHEMBL953
Synonyms
Chemical data
Formula	C14H15N3O5
Molecular mass	305.286 g/mol
	SMILES [O-][N+](=O)c1cc(\C=C(/C#N)C(=O)N(CC)CC)cc(O)c1O ;
	InChI InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+ ; Key:JRURYQJSLYLRLN-BJMVGYQFSA-N ;
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英: entacapone
商: コムタン
関: レボドパ、カルビドパ、カテコール-O-メチルトランスフェラーゼ COMT; 抗パーキンソン剤

末梢COMT阻害薬であり、レボドパ・カルビドパ又はレボドパ・塩酸ベンセラジドと併用され、レボドパから3-O-メチルドパ(3-OMD)の代謝経路を阻害することでレボドパの生物学的利用率を増大させ、そのため血中レボドパの脳内移行を効率化する。

[1] Singer C (2002). "Adverse effects in the treatment of Parkinson’s disease". Expert Review of Neurotherapeutics 2 (1): 105–118. doi:10.1586/14737175.2.1.105.

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entacapone