Tepoxalin | CAS#103475-41-8 | 5-lipoxygenase inhibitor

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

MedKoo CAT#: 328069

CAS#: 103475-41-8

Description: 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

CAS# 103475-41-8

Instruction

Theoretical Analysis

MedKoo Cat#: 328069
Name: Tepoxalin
CAS#: 103475-41-8
Chemical Formula: C20H20ClN3O3
Exact Mass: 385.12
Molecular Weight: 385.848
Elemental Analysis: C, 62.26; H, 5.22; Cl, 9.19; N, 10.89; O, 12.44

Price and Availability

Size	Price	Availability
5mg	USD 350	2 Weeks
10mg	USD 595	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. PubMed PMID: 24961730.

2: 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. PubMed PMID: 24813477.

3: McCarthy RJ. Tepoxalin no longer available commercially. Am J Vet Res. 2013 Jul;74(7):948. doi: 10.2460/ajvr.74.7.948. PubMed PMID: 23802664.

4: 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. PubMed PMID: 23718664.

5: 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. PubMed PMID: 23349526.

6: 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. PubMed PMID: 22986275.

7: 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. PubMed PMID: 22726277.

8: 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. PubMed PMID: 22240988.

9: 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. PubMed PMID: 21962280.

10: 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. PubMed PMID: 21569197.

11: 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. PubMed PMID: 21497474.

12: 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. PubMed PMID: 21348304.

13: de Boever S, Neirinckx EA, Meyer E, de Baere S, Beyaert R, de Backer P, Croubels S. Pharmacodynamics of tepoxalin, sodium-salicylate and ketoprofen in an intravenous lipopolysaccharide inflammation model in broiler chickens. J Vet Pharmacol Ther. 2010 Dec;33(6):564-72. doi: 10.1111/j.1365-2885.2010.01184.x. PubMed PMID: 21062309.

14: Giorgi M, Cuniberti B, Ye G, Barbero R, Sgorbini M, Vercelli C, Corazza M, Re G. Oral administration of tepoxalin in the horse: a PK/PD study. Vet J. 2011 Oct;190(1):143-9. doi: 10.1016/j.tvjl.2010.09.013. PubMed PMID: 21036634.

15: Goodman LA, Torres BT, Reynolds LR, Budsberg SC. Effects of firocoxib, meloxicam, and tepoxalin administration on eicosanoid production in target tissues of healthy cats. Am J Vet Res. 2010 Sep;71(9):1067-73. doi: 10.2460/ajvr.71.9.1067. PubMed PMID: 20807147.

16: Macrory L, Vaughan-Thomas A, Clegg PD, Innes JF. An exploration of the ability of tepoxalin to ameliorate the degradation of articular cartilage in a canine in vitro model. BMC Vet Res. 2009 Jul 22;5:25. doi: 10.1186/1746-6148-5-25. PubMed PMID: 19624842; PubMed Central PMCID: PMC2719625.

17: Gilmour MA, Lehenbauer TW. Comparison of tepoxalin, carprofen, and meloxicam for reducing intraocular inflammation in dogs. Am J Vet Res. 2009 Jul;70(7):902-7. doi: 10.2460/ajvr.70.7.902. PubMed PMID: 19566476.

18: Horvath-Ungerboeck C, Thoday KL, Shaw DJ, van den Broek AH. Tepoxalin reduces pruritus and modified CADESI-01 scores in dogs with atopic dermatitis: a prospective, randomized, double-blinded, placebo-controlled, cross-over study. Vet Dermatol. 2009 Aug;20(4):233-42. doi: 10.1111/j.1365-3164.2009.00739.x. PubMed PMID: 19552701.

19: Goodman L, Torres B, Punke J, Reynolds L, Speas A, Ellis A, Budsberg S. Effects of firocoxib and tepoxalin on healing in a canine gastric mucosal injury model. J Vet Intern Med. 2009 Jan-Feb;23(1):56-62. doi: 10.1111/j.1939-1676.2008.0226.x. PubMed PMID: 19175721.

20: De Boever S, Neirinckx E, Baert K, De Backer P, Croubels S. Pharmacokinetics of tepoxalin and its active metabolite in broiler chickens. J Vet Pharmacol Ther. 2009 Feb;32(1):97-100. doi: 10.1111/j.1365-2885.2008.01000.x. PubMed PMID: 19161461.

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