| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H11NO6 |
| Molecular Weight | 265.2188 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)C(=CC1=CC(=C(O)C(O)=C1)[N+]([O-])=O)C(C)=O
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
| Molecular Formula | C12H11NO6 |
| Molecular Weight | 265.2188 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| 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.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
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.
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TARGET -> INHIBITOR |
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