| Identification | Back Directory | [Name]
Nitecapone | [CAS]
116313-94-1 | [Synonyms]
OR 462
Nitecapone
3-(3,4-Dihydroxy-5-nitrobenzylidene)pentane-2,4-dione
3-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-2,4-pentanedione | [Molecular Formula]
C12H11NO6 | [MDL Number]
MFCD00866318 | [MOL File]
116313-94-1.mol | [Molecular Weight]
265.22 |
| Questions And Answer | Back Directory | [Description]
Nitecapone (OR-462) is a drug which acts as a selective inhibitor of the enzyme catechol O-methyl transferase (COMT).It was patented as an antiparkinson medication. | [In vitro]
Nitecapone (1-100 μM) reducesd GSH (reduced glutathione) depletion induced by ROO-by 11-38% and oxidation to oxidized glutathione (GSSG) by 32-45%.MCE has not independently confirmed the accuracy of these methods. They are for reference only. | [Biological activity]
Nitecapone (OR-462) is a short-acting, orally active, catechol-O-methyltransferase (COMT) inhibitor with gastrointestinal protective and antioxidant activity. Nitecapone (OR-462) scavenges reactive oxygen species and nitric oxide and prevents lipid peroxidation. |
| Chemical Properties | Back Directory | [Melting point ]
171-173°C | [Boiling point ]
495.3±45.0 °C(Predicted) | [density ]
1.451±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO: soluble15mg/mL, clear | [form ]
powder | [pka]
5.60±0.50(Predicted) | [color ]
white to beige | [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 | [InChIKey]
UPMRZALMHVUCIN-UHFFFAOYSA-N | [SMILES]
[N+](=O)([O-])c1c(c(cc(c1)C=C(C(=O)C)C(=O)C)O)O |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1 / PGIII | [WGK Germany ]
3 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral | [Toxicity]
mouse,LD50,intraperitoneal,507mg/kg (507mg/kg),Pharmacology and Toxicology Vol. 69, Pg. 64, 1991. |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
Inhibitor for the treatment of Parkinson disease | [Uses]
Inhibitor for the treatment of Parkinson's disease. | [Definition]
ChEBI: Nitecapone is a hydroxycinnamic acid. | [in vivo]
Nitecapone (30 mg/kg, ip daily for 13 days) reduces development and symptoms of neuropathic pain after spinal nerve ligation in rats[3]. | Animal Model: | Eighty-six male Wistar rats, weighing 140-350 g[3]. | | Dosage: | 30 mg/kg (3.3 mL/kg). | | Administration: | IP, once daily for 13 days. | | Result: | Selectively and specifically inhibits COMT in the peripheral tissues, and to some extent in the CNS for ca. 3 h.
Increased the thresholds for the mechanical stimuli and thus reduced mechanical allodynia.
Reduced the number of positive reactions of the ipsilateral paws when compared with the baselines in the nitecapone-pretreated rats.
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