Tepoxalin

Tepoxalin
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATCvet code	QM01AE92 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: ℞-only;
Identifiers
	IUPAC name 3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]-N-hydroxy-N-methylpropanamide;
CAS Number	103475-41-8 ;
PubChem CID	59757;
ChemSpider	53906 ;
UNII	TZ4OX61974;
KEGG	D06075 ;
ChEBI	CHEBI:76277 ;
CompTox Dashboard (EPA)	DTXSID1057610 ;
ECHA InfoCard	100.166.553
Chemical and physical data
Formula	C20H20ClN3O3
Molar mass	385.85 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C(=O)CCc1cc(n(n1)c2ccc(cc2)OC)c3ccc(cc3)Cl)O;
	InChI 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 ; Key:XYKWNRUXCOIMFZ-UHFFFAOYSA-N ;
	(what is this?) (verify)

Tepoxalin, formerly sold under the brand name Zubrin,^[1] is a non-steroidal anti-flammatory drug (NSAID).

Tepoxalin was withdrawn from the American market by the manufacturer and is not marketed by any manufacturer as of 2024.

Tepoxalin was used as anti-inflammatory and analgesic in the dog prior to withdrawal.

Approval

Tepoxalin received FDA approval for use in the dog in 1998.^[2]

Tepoxalin was taken off the market by the manufacturer in the US. However, it still has Food and Drug Administration (FDA) approval.^[1] As of 2024 it is no marketed by any manufacturer.^[3]

Pharmacology

The drug works as a nonsteroidal anti-inflammatory drug (NSAID). It inhibits both cyclooxygenase and lipoxygenase enzymes suppressing biosynthesis of prostaglandins and leukotrienes, respectively. In vitro results have shown it be more selective for cyclooxygenase-1. It is highly protein bound.^[1]

The half-life of tepoxalin in the dog is 2 hours, with a 13 hour half-life for the acid metabolite.^[1]

Use

Tepoxalin was used to treat both acute and chronic pain and inflammation. Tepoxalin has been used for surgical pain but its primary use was for osteoarthritis. Tepoxalin has been shown to be more effective than meloxicam and carprofen for intraarticular inflammation and ocular inflammation but less effective for dermatitis and ineffective for respiratory disease.^[1]

Adverse effects are similar to other NSAIDs and relate to the gastrointestinal system. Common adverse effects are emesis, diarrhoea, nausea, and gastric ulceration. Studies have not shown haemostatic or renal effects, although these are likely to occur at high enough doses. The LD50 is unknown but doses up to 30 times the recommended amount have been given to dogs without serious adverse effect and doses of 10mg/kg did not produce adverse effect in cats.^[1]

Tepoxalin was never investigated in large animals.^[1]

References

1 2 3 4 5 6 7 Papich MG (2016). "Tepoxalin". Saunders Handbook of Veterinary Drugs Small and Large Animal (4th ed.). Elsevier. p. 762. ISBN 978-0-323-24485-5.
↑ Odeh D, Odeh M, Hafez T, Hassan A (January 2025). "Bioactive Fused Pyrazoles Inspired by the Adaptability of 5-Aminopyrazole Derivatives: Recent Review". Molecules. 30 (2). Basel, Switzerland: MDPI: 366. doi:10.3390/molecules30020366. PMC 11767260. PMID 39860235.
↑ Papich MG (2024-06-26). "Non‐Steroidal Anti‐Inflammatory Drugs". In Lamont L, Grimm K, Robertson S, Love L, Schroeder C (eds.). Veterinary Anesthesia and Analgesia. Wiley. pp. 398–419. doi:10.1002/9781119830306.ch24. ISBN 978-1-119-83027-6.

[saunders-1] 1 2 3 4 5 6 7 Papich MG (2016). "Tepoxalin". Saunders Handbook of Veterinary Drugs Small and Large Animal (4th ed.). Elsevier. p. 762. ISBN 978-0-323-24485-5.

[2] Odeh D, Odeh M, Hafez T, Hassan A (January 2025). "Bioactive Fused Pyrazoles Inspired by the Adaptability of 5-Aminopyrazole Derivatives: Recent Review". Molecules. 30 (2). Basel, Switzerland: MDPI: 366. doi:10.3390/molecules30020366. PMC 11767260. PMID 39860235.

[Papich_2024-3] Papich MG (2024-06-26). "Non‐Steroidal Anti‐Inflammatory Drugs". In Lamont L, Grimm K, Robertson S, Love L, Schroeder C (eds.). Veterinary Anesthesia and Analgesia. Wiley. pp. 398–419. doi:10.1002/9781119830306.ch24. ISBN 978-1-119-83027-6.

[1]

[2]

[3]

v t e Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Grapiprant^‡ Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Meloxicam/rizatriptan Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
category commons portal