General
Preferred name
opicapone
Synonyms
BIA 9-1067 ()
Ontilyv ()
BIA-9-1067 ()
Ongentys ()
Opicapona ()
BIA-91067 ()
P&D ID
PD073883
CAS
923287-50-7
Tags
available
drug
Approved by
EMA
PMDA
FDA
First approval
2016
Drug indication
Parkinson disease
Drug Status
approved
investigational
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ABSORPTION
Oral opicapone demonstrates linear, dose-dependent absorption. However, following simultaneous ingestion of a high-fat, high-calorie meal, the maximal plasma concentration is decreased [L2337].; ; tmax of 1.0 h to 2.5 h after once-daily multiple-dose administration of up to 50 mg opicapone [L2343].;
HALF-LIFE
1.58-4.50h [L2339]; ; Despite the short half-life, the observed half-life of opicapone-induced COMT inhibition in human red blood cells was 61.6 h (standard deviation [SD] = 37.6 h) [A32590].
PHARMACODYNAMICS
Opicapone (OPC) is a powerful, reversible, and strictly peripheral third-generation catechol-O-methyltransferase inhibitor (COMT) inhibitor, which improves levodopa (L-Dopa) availability. It serves as adjunct therapy for L-Dopa treated patients with Parkinson's disease and motor fluctuations [L2337].; ; Opicapone showed a significant (>90%) and long-lasting (>24 hours) COMT inhibition in healthy subjects after administration of a 50 mg dose [L2343].; ; In 14- to 15-week, double-blind, multinational trials and in 1-year, open-label studies, opicapone demonstrated to be an effective and generally well tolerated adjunct therapy to L-Dopa plus a dopa decarboxylase inhibitor and other Parkinson disease therapy. During the double-blind phase, adjunctive opicapone 50 mg once daily provided significantly greater improvements in motor fluctuations than placebo, with these improvements noninferior to those with entacapone. These beneficial improvements in motor fluctuations with opicapone were maintained in patients who continued adjunctive opicapone during the extension studies, with patients who switched from placebo or entacapone to opicapone experiencing significant improvements in motor fluctuations during this year [A32588].
MOA
Opicapone is a peripheral, selective and reversible catechol-O-methyltransferase (COMT) inhibitor endowed with a high binding affinity (sub-picomolar) that results in a slow complex dissociation rate constant and long-term action (>24 hours) in vivo [L2343].; ; In the presence of a DOPA decarboxylase inhibitor (DDCI), COMT acts as the primary metabolizing enzyme for levodopa, catalyzing the conversion to 3-O-methyldopa (3-OMD) in both the brain and periphery. In those taking levodopa and a peripheral DDCI, such as carbidopa or benserazide, opicapone augments levodopa plasma levels, thereby enhancing the efficacy of levodopa [L2343].
METABOLISM
Sulphation appears to be the main metabolic pathway for this drug [A32590].; Other metabolic pathways include reduction, methylation, and glucuronidation [L2341].; ; Opicapone undergoes N-oxide reduction to BIA 9-1079, an active metabolite, and this is the main metabolite in monkeys, and is less significant in rats and mice however. In humans, this metabolite is not detectable. However, human metabolism results in an an inactive metabolite _BIA 9-1103_, the result of 3-O-sulphation, and BIA 9-1104, the result of 4-O-methylation. BIA 9-1103 has been measured in mouse, rat and monkey samples, and BIA 9-1104 detected in negligible amounts in the mini-pig, rat and mouse samples, and therefore no unique human metabolites are present and all can be detected in at least one of the non-clinical species. Two have been examined with significance, BIA 9-1079 and BIA 9-1103 [L2341].;
DESCRIPTION
Opicapone (BIA 9-1067) is a potent third-generation catechol-O-methyltransferase (COMT) inhibitor for the research of Parkinson's disease and motor fluctuations. Opicapone decreases the ATP content of the cells with an IC50 of 98 ¦ÌM[1].
PRICE
87
DESCRIPTION
Opicapone (BIA 9-1067) reduces the ATP content of the cells (IC50: 98 ??M). Opicapone is an effective third-generation catechol-O-methyltransferase inhibitor for the research of Parkinson's disease and motor fluctuations.
DESCRIPTION
Opicapone (BIA 9-1067) reduces the ATP content of the cells (IC50: 98 μM). Opicapone is an effective third-generation catechol-O-methyltransferase inhibitor for the research of Parkinson's disease and motor fluctuations.
(TargetMol Bioactive Compound Library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
16
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
EU-OPENSCREEN Bioactive Compound Library
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
30
Molecular Weight
412.0
Hydrogen Bond Acceptors
8
Hydrogen Bond Donors
2
Rotatable Bonds
3
Ring Count
3
Aromatic Ring Count
3
cLogP
3.28
TPSA
149.46
Fraction CSP3
0.13
Chiral centers
0.0
Largest ring
6.0
QED
0.17
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
COMT
MOA
catechol O methyltransferase inhibitor
Pathway
Metabolism
Metabolic Enzyme/Protease
Neuronal Signaling
Source data
