Entacapone

Catechol-O-Methyltransferase Inhibitor — NERVOUS SYSTEM

Key facts

Entacapone is an ofp drug in the Catechol-O-Methyltransferase Inhibitor class catalogued in DrugCentral. It was first approved by the FDA in 1999. Its mechanism of action is classified as Catechol O-Methyltransferase Inhibitors. DrugCentral lists 6 molecular targets, including COMT, Comt and MPC2. Recorded indications include Parkinson's disease.

• Approval status: ofp (first approved 1999 by the FDA).
• Drug class: Catechol-O-Methyltransferase Inhibitor.
• Mechanism of action: Catechol O-Methyltransferase Inhibitors.
• Molecular targets: COMT, Comt, MPC2 and MPC1L (6 listed in DrugCentral).
• Indications: Parkinson's disease.
• ATC code: N04BX02 (Other dopaminergic agents).
• Molecular formula: C14H15N3O5; molecular weight 305.29 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (1)

• Parkinson's disease

Contraindications (27)

• Acute disease of cardiovascular system
• Angle-closure glaucoma
• Cardiovascular event risk
• Conduction disorder of the heart
• Depressive disorder
• Diabetes mellitus
• Diarrhea
• Disease of liver
• Disorder of lung
• Drug-induced psychosis
• Duodenal ulcer disease
• Dyskinesia
• Gastric ulcer
• Gastrointestinal hemorrhage
• Hallucinations
• Kidney disease
• Malignant melanoma
• Myocardial infarction
• Obstruction of bile duct
• Open-angle glaucoma
• Orthostatic hypotension
• Peptic ulcer
• Psychoneurotic personality disorder
• Psychotic disorder
• Retention of urine
• Seizure disorder
• Suicidal thoughts

Mechanism & targets

• Mechanism of action (MoA): Catechol O-Methyltransferase Inhibitors
• Established pharmacologic class: Catechol-O-Methyltransferase Inhibitor

Molecular targets (6)

Target	Gene	Action	Activity
Catechol O-methyltransferase	COMT	inhibitor	Ki 9.52
Catechol O-methyltransferase	Comt	unknown	IC50 7.89
Mitochondrial pyruvate carrier 2	MPC2	inhibitor	IC50 6.22
Mitochondrial pyruvate carrier 1-like protein	MPC1L	inhibitor	IC50 6.20
Alpha-ketoglutarate-dependent dioxygenase FTO	FTO	unknown	IC50 5.52
G-protein coupled receptor 35	GPR35	unknown	EC50 5.25

Regulatory approvals (2)

Date	Agency	Marketed as	Applicant	Orphan
2011-02-18	EMA	—	Teva Pharma B.V.
1999-10-19	FDA	—	ORION PHARMA

ATC classification

ATC code	Therapeutic hierarchy
N04BX02	NERVOUS SYSTEM › ANTI-PARKINSON DRUGS › DOPAMINERGIC AGENTS › Other dopaminergic agents

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Dyskinesia	945.9
On and off phenomenon	637.3
Hallucination	572.2
Hallucination, visual	387.7
Freezing phenomenon	359.9
Muscle rigidity	313.5
Delusion	220.6
Gambling disorder	203.1
Dystonia	202.8
Hypersexuality	198.3
Psychotic disorder	164.7
Fall	157.3

Chemical structure

Full physicochemical, ADMET and 3D-structure analysis of Entacapone is on its molecule page.

• Molecular formula: C₁₄H₁₅N₃O₅
• Molecular weight: 305.29 g/mol
• CAS number: 130929-57-6
• InChIKey: JRURYQJSLYLRLN-BJMVGYQFSA-N
• PubChem CID: 5281081

CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Entacapone used for?

DrugCentral lists the following indications for Entacapone: Parkinson's disease.

How does Entacapone work?

Entacapone is classified as Catechol O-Methyltransferase Inhibitors; its molecular targets in DrugCentral include COMT (inhibitor), Comt, MPC2 (inhibitor) and MPC1L (inhibitor).

When was Entacapone first approved?

Entacapone was first approved by the FDA in 1999.

What drug class does Entacapone belong to?

Entacapone is in the Catechol-O-Methyltransferase Inhibitor class.

What is the chemical formula of Entacapone?

Entacapone has the molecular formula C14H15N3O5 and a molecular weight of 305.29 g/mol.

Sources

• DrugCentral drug card 1018 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL953 — compound record and bioactivity
• PubChem CID 5281081 — chemical identifiers
• DrugBank DB00494 — drug record
• FDA UNII 4975G9NM6T — substance identity
• DailyMed: FDA labels for Entacapone — current prescribing information (label search)
• UniProt P21964 (COMT) — target protein
• UniProt O95563 (MPC2) — target protein
• UniProt P0DKB6 (MPC1L) — target protein
• UniProt Q9C0B1 (FTO) — target protein
• UniProt Q9HC97 (GPR35) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral

How this page is built: methodology · editorial policy & corrections.