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MedKoo Cat#: 328069 | Name: Tepoxalin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tepoxalin, also known as ORF-20485; RWJ-20485; is a 5-lipoxygenase inhibitor potentially for the treatment of asthma, osteoarthritis (OA). Tepoxalin has in vivo inhibitory activity against COX-1, COX-2, and 5-LOX in dogs at the current approved recommended dosage.Tepoxalin inhibits inflammation and microvascular dysfunction induced by abdominal irradiation in rats. Tepoxalin enhances the activity of an antioxidant, pyrrolidine dithiocarbamate, in attenuating tumor necrosis factor alpha-induced apoptosis in WEHI 164 cells.

Chemical Structure

Tepoxalin
Tepoxalin
CAS#103475-41-8

Theoretical Analysis

MedKoo Cat#: 328069

Name: Tepoxalin

CAS#: 103475-41-8

Chemical Formula: C20H20ClN3O3

Exact Mass: 385.1193

Molecular Weight: 385.85

Elemental Analysis: C, 62.26; H, 5.22; Cl, 9.19; N, 10.89; O, 12.44

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 595.00 2 Weeks
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Related CAS #
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Synonym
Tepoxalin; ORF-20485; ORF20485; ORF 20485; RWJ-20485; RWJ 20485; RWJ20485.
IUPAC/Chemical Name
5-(4-Chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide
InChi Key
XYKWNRUXCOIMFZ-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C(N(O)C)CCC1=NN(C2=CC=C(OC)C=C2)C(C3=CC=C(Cl)C=C3)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 385.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kästner SB, Amon T, Tünsmeyer J, Noll M, Söbbeler FJ, Laakso S, Saloranta L, Huhtinen M. Effects of tasipimidine premedication with and without methadone and dexmedetomidine on cardiovascular variables during propofol-isoflurane anaesthesia in Beagle dogs. Vet Anaesth Analg. 2024 May-Jun;51(3):253-265. doi: 10.1016/j.vaa.2024.03.005. Epub 2024 Mar 14. PMID: 38580536. 2: Sousa SM, Xavier CPR, Vasconcelos MH, Palmeira A. Repurposing some of the Well-known Non-steroid Anti-inflammatory Drugs (NSAIDs) for Cancer Treatment. Curr Top Med Chem. 2023;23(13):1171-1195. doi: 10.2174/1568026623666230130150029. PMID: 36717997. 3: McQuerry JA, Chen J, Chang JT, Bild AH. Tepoxalin increases chemotherapy efficacy in drug-resistant breast cancer cells overexpressing the multidrug transporter gene ABCB1. Transl Oncol. 2021 Oct;14(10):101181. doi: 10.1016/j.tranon.2021.101181. Epub 2021 Jul 20. PMID: 34298440; PMCID: PMC8322466. 4: Corsello SM, Nagari RT, Spangler RD, Rossen J, Kocak M, Bryan JG, Humeidi R, Peck D, Wu X, Tang AA, Wang VM, Bender SA, Lemire E, Narayan R, Montgomery P, Ben-David U, Garvie CW, Chen Y, Rees MG, Lyons NJ, McFarland JM, Wong BT, Wang L, Dumont N, O'Hearn PJ, Stefan E, Doench JG, Harrington CN, Greulich H, Meyerson M, Vazquez F, Subramanian A, Roth JA, Bittker JA, Boehm JS, Mader CC, Tsherniak A, Golub TR. Discovering the anti-cancer potential of non-oncology drugs by systematic viability profiling. Nat Cancer. 2020 Feb;1(2):235-248. doi: 10.1038/s43018-019-0018-6. Epub 2020 Jan 20. PMID: 32613204; PMCID: PMC7328899. 5: Lu X, Huang L, Zhang W, Ning X. Tepoxalin a dual 5-LOX-COX inhibitor and erlotinib an EGFR inhibitor halts progression of gastric cancer in tumor xenograft mice. Am J Transl Res. 2018 Nov 15;10(11):3847-3856. PMID: 30662635; PMCID: PMC6291731. 6: Lopes C, Carregaro AB, Freitas GC, Padilha VS, Lukarsewski R, Paim FC, Lopes ST. Effect of tepoxalin on renal function and hepatic enzymes in dogs exposed to hypotension with isoflurane. Vet Anaesth Analg. 2014 Sep;41(5):459-67. doi: 10.1111/vaa.12129. Epub 2014 Jun 25. PMID: 24961730. 7: Loftus JP, Cavatorta D, Bushey JJ, Levine CB, Sevier CS, Wakshlag JJ. The 5-lipoxygenase inhibitor tepoxalin induces oxidative damage and altered PTEN status prior to apoptosis in canine osteosarcoma cell lines. Vet Comp Oncol. 2016 Jun;14(2):e17-30. doi: 10.1111/vco.12094. Epub 2014 May 12. PMID: 24813477. 8: McCarthy RJ. Tepoxalin no longer available commercially. Am J Vet Res. 2013 Jul;74(7):948. doi: 10.2460/ajvr.74.7.948. PMID: 23802664. 9: Lomas AL, Lyon SD, Sanderson MW, Grauer GF. Acute and chronic effects of tepoxalin on kidney function in dogs with chronic kidney disease and osteoarthritis. Am J Vet Res. 2013 Jun;74(6):939-44. doi: 10.2460/ajvr.74.6.939. PMID: 23718664. 10: Charlton AN, Benito J, Simpson W, Freire M, Lascelles BD. Evaluation of the clinical use of tepoxalin and meloxicam in cats. J Feline Med Surg. 2013 Aug;15(8):678-90. doi: 10.1177/1098612X12473994. Epub 2013 Jan 24. PMID: 23349526; PMCID: PMC11191708. 11: Kushiro-Banker T, Keegan RD, Decourcey MA, Grubb TL, Greene SA, Armstrong R. Effects of tepoxalin and medetomidine on glomerular filtration rate in dogs. J Vet Med Sci. 2013 Jan 31;75(1):69-74. doi: 10.1292/jvms.12-0062. Epub 2012 Oct 14. PMID: 22986275. 12: Bosmans T, Piron K, Oosterlinck M, Gasthuys F, Duchateau L, Waelbers T, Samoy Y, Van Vynckt D, Polis I. Comparison of analgesic efficacy of epidural methadone or ropivacaine/methadone with or without pre-operative oral tepoxalin in dogs undergoing tuberositas tibiae advancement surgery. Vet Anaesth Analg. 2012 Nov;39(6):618-27. doi: 10.1111/j.1467-2995.2012.00744.x. Epub 2012 Jun 22. PMID: 22726277. 13: Goupil RC, Bushey JJ, Peters-Kennedy J, Wakshlag JJ. Prevalence of 5-lipoxygenase expression in canine osteosarcoma and the effects of a dual 5-lipoxygenase/cyclooxygenase inhibitor on osteosarcoma cells in vitro and in vivo. Vet Pathol. 2012 Sep;49(5):802-10. doi: 10.1177/0300985811432350. Epub 2012 Jan 27. PMID: 22287649. 14: Sunaga T, Oh N, Hosoya K, Takagi S, Okumura M. Pro-apoptotic effects of tepoxalin, a cyclooxygenase/lipoxygenase dual inhibitor, on canine synovial fibroblasts. J Vet Med Sci. 2012 Jun;74(6):745-50. doi: 10.1292/jvms.11-0435. Epub 2012 Jan 12. PMID: 22240988. 15: Burton NJ, Owen MR, Kirk LS, Toscano MJ, Colborne GR. Conservative versus arthroscopic management for medial coronoid process disease in dogs: a prospective gait evaluation. Vet Surg. 2011 Dec;40(8):972-80. doi: 10.1111/j.1532-950X.2011.00900.x. Epub 2011 Sep 23. PMID: 22091562. 16: Wakshlag JJ, Peters-Kennedy J, Bushey JJ, Loftus JP. 5-lipoxygenase expression and tepoxalin-induced cell death in squamous cell carcinomas in cats. Am J Vet Res. 2011 Oct;72(10):1369-77. doi: 10.2460/ajvr.72.10.1369. PMID: 21962280; PMCID: PMC10957241. 17: Sottnik JL, Hansen RJ, Gustafson DL, Dow SW, Thamm DH. Induction of VEGF by tepoxalin does not lead to increased tumour growth in a canine osteosarcoma xenograft. Vet Comp Oncol. 2011 Jun;9(2):118-30. doi: 10.1111/j.1476-5829.2010.00240.x. Epub 2010 Sep 13. PMID: 21569197. 18: Cuniberti B, Odore R, Barbero R, Cagnardi P, Badino P, Girardi C, Re G. In vitro and ex vivo pharmacodynamics of selected non-steroidal anti-inflammatory drugs in equine whole blood. Vet J. 2012 Mar;191(3):327-33. doi: 10.1016/j.tvjl.2011.03.016. Epub 2011 May 11. PMID: 21565533. 19: Giorgi M, Mengozzi G, Raffaelli A, Saba A. Characterization of in vivo plasma metabolites of tepoxalin in horses using LC-MS-MS. J Pharm Biomed Anal. 2011 Aug 25;56(1):45-53. doi: 10.1016/j.jpba.2011.03.028. Epub 2011 Mar 30. PMID: 21497474. 20: Guo XH, Zhang HW, Tao L, Li YJ, Wang PA, Wang SY, Wang Q, Dong LH, Chang JB. [Novel synthetic method and analgesic activity of tepoxalin]. Yao Xue Xue Bao. 2010 Oct;45(10):1260-4. Chinese. PMID: 21348304.