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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
Structure of NEBICAPONE

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

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

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
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 Sat Dec 16 17:55:01 GMT 2023
Edited
by admin
on Sat Dec 16 17:55:01 GMT 2023
Record UNII
NM2KXJ990T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEBICAPONE
INN  
INN  
Official Name English
1-(3,4-DIHYDROXY-5-NITROPHENYL)-2-PHENYLETHAN-1-ONE
Systematic Name English
nebicapone [INN]
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
PUBCHEM
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
DRUG BANK
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
CAS
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
SMS_ID
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
INN
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
NCI_THESAURUS
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
ChEMBL
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
FDA UNII
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
EPA CompTox
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
MESH
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
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