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

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-1 131 Target ID: CHEMBL2949 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8504	4.6 µM [IC50]
platelet aggregation 80 Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8504	0.045 µM [IC50]
Arachidonate 12-lipoxygenase 4 Target ID: CHEMBL3687 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8504	3.0 nM [IC50]
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL312 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996452	Inhibitor 8504	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 8583	ZUBRIN Approved Use ZUBRIN™ (tepoxalin) Tablets are indicated for the control of pain and inflammation associated with osteoarthritis in dogs. Launch Date 2003
Asthma 244 Sources: http://adisinsight.springer.com/drugs/800002043	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
219 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
450 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
466 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
516 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
427 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
909 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1406 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1344 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
667 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2113 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2916 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4923 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6851 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14737 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
21857 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
24896 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TEPOXALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739025/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	3-[5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)PYRAZOL-3-YL]PROPANOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

PubMed

Title	Date	PubMed
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.	2003-03	12629151
Effects of tepoxalin, a dual inhibitor of cyclooxygenase/5-lipoxygenase, on events associated with NSAID-induced gastrointestinal inflammation.	1997-06	9223651
Tepoxalin blocks neutrophil migration into cutaneous inflammatory sites by inhibiting Mac-1 and E-selectin expression.	1996-01	8566054
Tepoxalin, a novel dual inhibitor of the prostaglandin-H synthase cyclooxygenase and peroxidase activities.	1995-06-09	7775455
Suppression of NF kappa B activation and NF kappa B-dependent gene expression by tepoxalin, a dual inhibitor of cyclooxygenase and 5-lipoxygenase.	1995-02	7759567

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.

Name

Type

Language

TEPOXALIN

Official Name

English

ORF 20485

Preferred 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

Classification Tree Code System Code

CFR

21 CFR 520.2340