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
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 |
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Synthesis of 1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and derivatives as potent and long-acting peripheral inhibitors of catechol-O-methyltransferase. | 2002 Jan 31 |
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Pharmacokinetics and pharmacodynamics of BIA 3-202, a novel COMT inhibitor, during first administration to humans. | 2003 |
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Catechol-O-methyltransferase inhibition in erythrocytes and liver by BIA 3-202 (1-[3,4-dibydroxy-5-nitrophenyl]-2-phenyl-ethanone). | 2003 Jun |
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BIA 3-202, a novel catechol-O-methyltransferase inhibitor, reduces the peripheral O-methylation of L-DOPA and enhances its availability to the brain. | 2003 May |
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Pharmacokinetic-pharmacodynamic interaction between BIA 3-202, a novel COMT inhibitor, and levodopa/benserazide. | 2003 Nov |
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Pharmacokinetic-pharmacodynamic interaction between BIA 3-202, a novel COMT inhibitor, and levodopa/carbidopa. | 2004 Jan-Feb |
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Human metabolism of nebicapone (BIA 3-202), a novel catechol-o-methyltransferase inhibitor: characterization of in vitro glucuronidation. | 2006 Nov |
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Gateways to clinical trials. | 2007 Apr |
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Catechol-O-methyltransferase and its inhibitors in Parkinson's disease. | 2007 Fall |
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Problems with the present inhibitors and a relevance of new and improved COMT inhibitors in Parkinson's disease. | 2010 |
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Toxicology and safety of COMT inhibitors. | 2010 |
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).
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C471
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C38149
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C433466
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ACTIVE MOIETY
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