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Details

Stereochemistry ACHIRAL
Molecular Formula C14H15N3O5
Molecular Weight 305.286
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ENTACAPONE

SMILES

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

InChI

InChIKey=JRURYQJSLYLRLN-BJMVGYQFSA-N
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+

HIDE SMILES / InChI

Molecular Formula C14H15N3O5
Molecular Weight 305.286
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Entacapone is a selective, reversible catechol-O-methyl transferase (COMT) inhibitor for the treatment of Parkinson's disease. It is a member of the class of nitrocatechols. When administered concomittantly with levodopa and a decarboxylase inhibitor (e.g., carbidopa), increased and more sustained plasma levodopa concentrations are reached as compared to the administration of levodopa and a decarboxylase inhibitor. The mechanism of action of entacapone is believed to be through its ability to inhibit COMT in peripheral tissues, altering the plasma pharmacokinetics of levodopa. When entacapone is given in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are greater and more sustained than after administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. It is believed that at a given frequency of levodopa administration, these more sustained plasma levels of levodopa result in more constant dopaminergic stimulation in the brain, leading to a greater reduction in the manifestations of parkinsonian syndrome. Entacapone is used as an adjunct to levodopa / carbidopa in the symptomatic treatment of patients with idiopathic Parkinson's Disease who experience the signs and symptoms of end-of-dose "wearing-off".

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
151.0 nM [IC50]
76.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Comtan

Cmax

ValueDoseCo-administeredAnalytePopulation
1095 ng/mL
200 mg 10 times / day steady-state, oral
ENTACAPONE plasma
Homo sapiens
1325 ng/mL
200 mg 8 times / day multiple, oral
ENTACAPONE plasma
Homo sapiens
1.2 μg/mL
200 mg single, oral
ENTACAPONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1989 ng × h/mL
200 mg 10 times / day steady-state, oral
ENTACAPONE plasma
Homo sapiens
2084 ng × h/mL
200 mg 8 times / day multiple, oral
ENTACAPONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.8 h
200 mg 10 times / day steady-state, oral
ENTACAPONE plasma
Homo sapiens
1.3 h
200 mg 8 times / day multiple, oral
ENTACAPONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
ENTACAPONE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dose of Comtan (entacapone) is one 200 mg tablet administered concomitantly with each levodopa and carbidopa dose to a maximum of 8 times daily (200 mg x 8 = 1,600 mg per day). Comtan should always be administered in association with levodopa and carbidopa. Entacapone has no antiparkinsonian effect of its own.
Route of Administration: Oral
In Vitro Use Guide
Kinetic assays indicate that Comtan inhibits InhA activity by 47.0% at an entacapone concentration of approximately 80 uM.
Substance Class Chemical
Record UNII
4975G9NM6T
Record Status Validated (UNII)
Record Version