Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H11NO5 |
Molecular Weight | 273.2408 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(O)C(=CC(=C1)C(=O)CC2=CC=CC=C2)[N+]([O-])=O
InChI
InChIKey=MRFOLGFFTUGAEB-UHFFFAOYSA-N
InChI=1S/C14H11NO5/c16-12(6-9-4-2-1-3-5-9)10-7-11(15(19)20)14(18)13(17)8-10/h1-5,7-8,17-18H,6H2
Molecular Formula | C14H11NO5 |
Molecular Weight | 273.2408 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Nebicapone (BIA 3-202) is a reversible, and tight-binding peripheral inhibitor of the enzyme catechol-O-methyltransferase (COMT) being developed for use as an adjunct to levodopa/dopa decarboxylase inhibitor in the treatment of PD. Nebicapone dose dependently and significantly decreased COMT activity. Nebicapone also increased systemic exposure to levodopa and improved motor response. The tight-binding nature of the inhibition produced by BIA 3-202 was evaluated by performing an Ackermann-Potter plot. The true K(i) for BIA 3-202, derived from the nonlinear regression analysis, was 0.19+/-0.02 nM. In substrate competition studies, an increase in the concentration of adrenaline resulted in a linear increase in IC(50) values for BIA 3-202.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacokinetics and pharmacodynamics of BIA 3-202, a novel COMT inhibitor, during first administration to humans. | 2003 |
|
Kinetic inhibitory profile of BIA 3-202, a novel fast tight-binding, reversible and competitive catechol-O-methyltransferase inhibitor. | 2003 Jan 24 |
|
Molecular modeling and metabolic studies of the interaction of catechol-O-methyltransferase and a new nitrocatechol inhibitor. | 2003 Mar |
|
Effect of nebicapone on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects. | 2008 Oct |
|
Toxicology and safety of COMT inhibitors. | 2010 |
|
A double-blind, randomized, placebo and active-controlled study of nebicapone for the treatment of motor fluctuations in Parkinson's disease. | 2010 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19922897
During the different treatment periods, subjects received a single dose of controlled-release levodopa 100 mg/benserazide 25 mg concomitantly with nebicapone 50, 100, and 200 mg or placebo. When administered concomitantly with a single dose of controlled-release levodopa 100 mg/benserazide 25 mg, single doses of nebicapone 50, 100, and 200 mg were well tolerated in these healthy adult volunteers, and dose dependently inhibited S-COMT activity and reduced 3-OMD formation compared with placebo.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19505437
Nebicapone inhibited rat liver COMT with a lower K(i) than mouse liver COMT (respectively 0.2nM vs. 1.2nM).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:55:01 GMT 2023
by
admin
on
Sat Dec 16 17:55:01 GMT 2023
|
Record UNII |
NM2KXJ990T
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C471
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
||
|
NCI_THESAURUS |
C38149
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
9838389
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
DB14849
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
274925-86-9
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
300000036953
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
8602
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
C83923
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
CHEMBL160038
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
NM2KXJ990T
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
DTXSID30181912
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY | |||
|
C433466
Created by
admin on Sat Dec 16 17:55:03 GMT 2023 , Edited by admin on Sat Dec 16 17:55:03 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
||
|
TARGET -> INHIBITOR | |||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
METABOLITE -> PARENT |
MINOR
PLASMA
|
||
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
METABOLITE -> PARENT |
MINOR
PLASMA
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |