Tepoxalin

Names

[ Name ]:
Tepoxalin

[Synonym ]:
Zubrin
Tepoxalinum [Latin]
3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-methylpropanamide
1H-Pyrazole-3-propanamide, 5-(4-chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-
5-(4-chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide
Tepoxalin
Tepoxalin [USAN:INN]
Tepoxaline
Tepoxalina [Spanish]
Tepoxalina
3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]-N-hydroxy-N-methylpropanamide
3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N-hydroxy-N-methylpropanamide
Tepoxaline [French]

Biological Activity

[Description]:

Tepoxalin is a dual inhibitor of COX and 5-lipoxygenase (5-LO) with potent anti-inflammatory activity and a favorable gastrointestinal profile[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase

[References]

[1]. Argentieri DC, et al. Tepoxalin: a dual cyclooxygenase/5-lipoxygenase inhibitor of arachidonic acid metabolism with potent anti-inflammatory activity and a favorable gastrointestinal profile. J Pharmacol Exp Ther. 1994 Dec;271(3):1399-408.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
573.0±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₂₀ClN₃O₃

[ Molecular Weight ]:
385.844

[ Flash Point ]:
300.3±32.9 °C

[ Exact Mass ]:
385.119324

[ PSA ]:
67.59000

[ LogP ]:
3.84

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.610

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ8002500

CHEMICAL NAME :: 1H-Pyrazole-3-propanamide, 5-(4-chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-me thyl-

CAS REGISTRY NUMBER :: 103475-41-8

LAST UPDATED :: 199712

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C20-H20-Cl-N3-O3

MOLECULAR WEIGHT :: 385.88

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1085 mg/kg/31D-I

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 33,38,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7280 mg/kg/26W-I

TOXIC EFFECTS :: Liver - changes in liver weight Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 33,38,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 54600 mg/kg/26W-I

TOXIC EFFECTS :: Gastrointestinal - alteration in gastric secretion Gastrointestinal - ulceration or bleeding from stomach

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 33,38,1996

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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