TEPOXALIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H20ClN3O3
Molecular Weight	385.844
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)N2N=C(CCC(=O)N(C)O)C=C2C3=CC=C(Cl)C=C3

InChI

InChIKey=XYKWNRUXCOIMFZ-UHFFFAOYSA-N

InChI=1S/C20H20ClN3O3/c1-23(26)20(25)12-7-16-13-19(14-3-5-15(21)6-4-14)24(22-16)17-8-10-18(27-2)11-9-17/h3-6,8-11,13,26H,7,12H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C20H20ClN3O3
Molecular Weight	385.844
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452

Tepoxalin is a nonsteroidal anti-inflammatory drug approved for veterinary use in the United States and many other countries. Marketed under the brand name Zubrin, Tepoxalin is indicated for the control of pain and inflammation associated with osteoarthritis in dogs. Tepoxalin has an unique property as an NSAIDs that suppresses both cyclooxygenase and lipoxygenase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-1 127 Target ID: CHEMBL2949 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8297	4.6 µM [IC50]
platelet aggregation 76 Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8297	0.045 µM [IC50]
Arachidonate 12-lipoxygenase 4 Target ID: CHEMBL3687 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8297	3.0 nM [IC50]
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL312 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8297	0.15 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 157 Sources: https://www.petplace.com/article/drug-library/drug-library/library/tepoxalin-zubrin-for-dogs/	Primary		Approved 8429	ZUBRIN Approved Use ZUBRIN™ (tepoxalin) Tablets are indicated for the control of pain and inflammation associated with osteoarthritis in dogs. Launch Date 2003
Asthma 241 Sources: http://adisinsight.springer.com/drugs/800002043	Primary		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Suppression of NF kappa B activation and NF kappa B-dependent gene expression by tepoxalin, a dual inhibitor of cyclooxygenase and 5-lipoxygenase.	1995 Feb	7759567
Tepoxalin, a novel dual inhibitor of the prostaglandin-H synthase cyclooxygenase and peroxidase activities.	1995 Jun 9	7775455
Tepoxalin blocks neutrophil migration into cutaneous inflammatory sites by inhibiting Mac-1 and E-selectin expression.	1996 Jan	8566054
Effects of tepoxalin, a dual inhibitor of cyclooxygenase/5-lipoxygenase, on events associated with NSAID-induced gastrointestinal inflammation.	1997 Jun	9223651
Toxicity of human monocytic THP-1 cells and microglia toward SH-SY5Y neuroblastoma cells is reduced by inhibitors of 5-lipoxygenase and its activating protein FLAP.	2003 Mar	12629151

Patents

Sample Use Guides

In Vivo Use Guide

Dogs: Administer 10 mg/kg (4.5 mg/lb) or 20 mg/kg (9.1 mg/lb) on the initial day of treatment, followed by a daily maintenance dose of 10 mg/kg.

Route of Administration: Oral

In Vitro Use Guide

Tepoxalin at 10(-5) M and 10(-6) M caused a decrease in collagen release from the canine cartilage explants, treated with IL-1beta and OSM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:39:46 GMT 2023` Edited by `admin` on `Fri Dec 15 15:39:46 GMT 2023`
Record UNII	TZ4OX61974
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TEPOXALIN

Official Name

English

TEPOXALIN [EMA EPAR VETERINARY]

Common Name

English

ZUBRIN

Common Name

English

TEPOXALIN [USAN]

Common Name

English

TEPOXALIN [GREEN BOOK]

Common Name

English

1H-PYRAZOLE-3-PROPANAMIDE, 5-(4-CHLOROPHENYL)-N-HYDROXY-1-(4-METHOXYPHENYL)-N-METHYL-

Systematic Name

English

ORF-20485

Code

English

tepoxalin [INN]

Common Name

English

5-(P-CHLOROPHENYL)-1-(P-METHOXYPHENYL)-N-METHYLPYRAZOLE-3-PROPIONOHYDROXAMIC ACID

Common Name

English

RWJ 20485

Code

English

RWJ-20485

Code

English

TEPOXALIN [MI]

Common Name

English

TEPOXALIN [MART.]

Common Name

English

ORF 20485

Code

English

Classification Tree Code System Code

CFR

21 CFR 520.2340