Nitecapone

Names

[ Name ]:
Nitecapone

[Synonym ]:
3-(3,4-dihydroxy-5-nitrobenzylidene)-2,4-pentanedione
2,4-Pentanedione,3-((3,4-dihydroxy-5-nitrophenyl)methylene)
Nitecapone
3-(3,4-dihydroxy-5-nitrophenyl)methylene-2,4-pentanedione
Nitecapona [INN-Spanish]
Nitecapone [INN]
OR 462
Nitecaponum [INN-Latin]

Biological Activity

[Description]:

Nitecapone (OR-462) is an orally active and short-acting catechol-O-methyltransferase (COMT) inhibitor with gastroprotective and antioxidant properties. Nitecapone (OR-462) scavenges reactive oxygen and nitric radicals and prevents lipid peroxidation[1][2][3].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> COMT

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

Signaling Pathways >> Metabolic Enzyme/Protease >> COMT

[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%[1].

[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.

[References]

[1]. Y J Suzuki, et al. Antioxidant properties of nitecapone (OR-462). Free Radic Biol Med. 1992 Nov;13(5):517-25.

[2]. Marcocci L, et al. Nitecapone: a nitric oxide radical scavenger. Biochemistry and Molecular Biology International, 01 Oct 1994, 34(3):531-541.

[3]. Oleg Kambur, et al. Nitecapone reduces development and symptoms of neuropathic pain after spinal nerve ligation in rats. Eur J Pain. 2011 Aug;15(7):732-40.

Chemical & Physical Properties

[ Density]:
1.451g/cm3

[ Boiling Point ]:
495.3ºC at 760 mmHg

[ Molecular Formula ]:
C₁₂H₁₁NO₆

[ Molecular Weight ]:
265.21900

[ Flash Point ]:
211.6ºC

[ Exact Mass ]:
265.05900

[ PSA ]:
120.42000

[ LogP ]:
2.09060

[ Vapour Pressure ]:
1.95E-10mmHg at 25°C

[ Index of Refraction ]:
1.645

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SA1942500

CHEMICAL NAME :: 2,4-Pentanedione, 3-((3,4-dihydroxy-5-nitrophenyl)methylene)-

CAS REGISTRY NUMBER :: 116313-94-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H11-N-O6

MOLECULAR WEIGHT :: 265.24

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 69,64,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 507 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 69,64,1991

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ RIDADR ]:
UN 2811 6.1 / PGIII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

D1-like dopamine receptor activation and natriuresis by nitrocatechol COMT inhibitors.

Kidney Int. 59(5) , 1683-94, (2001)

In recent years, several nitrocatechol derivatives (tolcapone, entacapone, and nitecapone) have been developed and found to be highly selective and potent inhibitors of catechol-O-methyltransferase (C...

Extending levodopa action: COMT inhibition.

Neurology 50(6 Suppl 6) , S27-32; discussion S44-8, (1998)

Degradation of levodopa in the periphery is known to be associated with motor fluctuations and dyskinesia in Parkinson's disease (PD) patients. The enzyme catechol-O-methyltransferase (COMT) is respon...

The Helicobacter felis mouse model in assessing anti-Helicobacter therapies and gastric mucosal prostaglandin E2 levels.

Scand. J. Gastroenterol. 31(4) , 334-8, (1996)

The aims of the present study were to assess the usefulness of the Helicobacter felis mouse model in the evaluation of antimicrobial therapies and the effect of Helicobacter infection on gastric mucos...