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Details

Stereochemistry ACHIRAL
Molecular Formula C12H11NO6
Molecular Weight 265.2193
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITECAPONE

SMILES

CC(=O)C(=Cc1cc(c(c(c1)O)O)N(=O)=O)C(=O)C

InChI

InChIKey=UPMRZALMHVUCIN-UHFFFAOYSA-N
InChI=1S/C12H11NO6/c1-6(14)9(7(2)15)3-8-4-10(13(18)19)12(17)11(16)5-8/h3-5,16-17H,1-2H3

HIDE SMILES / InChI

Molecular Formula C12H11NO6
Molecular Weight 265.2193
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Nitecapone (3-(3,4-dihydroxy-5-nitrobenzylidine)-2,4- pentanedione, OR-462) is a selective, short-acting catechol-O-methyltransferase (COMT) inhibitor, whose main site of action is in the gastrointestinal tract. Nitecapone displays in vivo activity in peripheral tissues but does not penetrate the blood-brain barrier. The compound increases mechanical and thermal nociception and reduces neuropathic pain in diabetic rats and in a spinal nerve ligation model. Nitecapone has been shown to have a protective effect against ischemia-reperfusion injury in experimental heart transplantation and in Langendorff preparations. Nitecapone added to cardioplegia solution reduces cardiac neutrophil accumulation and transcoronary neutrophil activation during clinical cardiopulmonary bypass. Reflected by better left ventricular stroke volume, nitecapone treatment may be an additional way of reducing the deleterious effects of neutrophil activation during cardiopulmonary bypass. Nitecapone was patented as an antiparkinsonian agent but was never marketed.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
18.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice.
2002 Jan-Feb
Novel screening assay for antioxidant protection against peroxyl radical-induced loss of protein function.
2007 Nov
Inhibitors of catechol-O-methyltransferase sensitize mice to pain.
2010 Dec
Patents

Sample Use Guides

100 mg of nitecapone t. d. s. orally for 7 days
Route of Administration: Oral
In Vitro Use Guide
Rubidium uptake was used as an index of Na+,K+-ATPase activity in LLCPK-1 cells. Briefly, confluent cells grown on six-well culture plates were incubated for 10 min with or without 1 mM ouabain. The cells were treated with 10 mM nitecapone in the presence or absence of 10 mM SCH23390 (D1 antagonist) for 20 min, and 0.05 ml of 50 mCiyml 86Rb1 was added to each well; after 2 min the cells were lysed and the radioactivity in the cell lysate was measured. Na+,K+-ATPase activity was determined as the difference in 86Rb+ uptake in the absence and presence of ouabain.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:15:56 UTC 2021
Edited
by admin
on Sat Jun 26 02:15:56 UTC 2021
Record UNII
98BS722498
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NITECAPONE
INN  
INN  
Official Name English
NITECAPONE [INN]
Common Name English
3-(3,4-DIHYDROXY-5-NITROBENZYLIDENE)-2,4-PENTANEDIONE
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C175164
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL167055
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
WIKIPEDIA
Nitecapone
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
EVMPD
SUB09312MIG
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
CAS
116313-94-1
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
INN
6514
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
PUBCHEM
5464105
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
FDA UNII
98BS722498
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
EPA CompTox
116313-94-1
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
MESH
C057364
Created by admin on Sat Jun 26 02:15:56 UTC 2021 , Edited by admin on Sat Jun 26 02:15:56 UTC 2021
PRIMARY
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ACTIVE MOIETY