116313-94-1

116313-94-1 structure

Name: Nitecapone
Chemical Name: 3-[(3,4-dihydroxy-5-nitrophenyl)methylidene]pentane-2,4-dione
CAS Number: 116313-94-1
Molecular Formula: C₁₂H₁₁NO₆
Molecular Weight: 265.21900
Catalog: Signaling Pathways Metabolic Enzyme/Protease COMT
Create Date: 2018-07-11 09:59:37
Modify Date: 2024-01-11 15:29:06
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].

Name	3-[(3,4-dihydroxy-5-nitrophenyl)methylidene]pentane-2,4-dione
Synonyms	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]

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.

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

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

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310
RIDADR	UN 2811 6.1 / PGIII

116313-85-0

123-54-6

~45%

116313-94-1

Literature: Journal of Medicinal Chemistry, , vol. 32, # 4 p. 841 - 846

Precursor 2
116313-85-0 123-54-6
DownStream 1
118724-88-2

56-41-7	108-65-6
56-35-9	64-17-5
67-56-1	108-88-3
141-78-6	1310-73-2
13463-67-7	1333-86-4