NAV

Tepoxalin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Tepoxalin
DrugBank Accession Number
DB11466
Background

Tepoxalin is a nonsteroidal anti-inflammatory drug approved for veterinary use in the United States and many other countries. It is primarily used to reduce inflammation and relief of pain caused by musculoskeletal disorders such as hip dysplasia and arthritis.

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 385.85
Monoisotopic: 385.1193192
Chemical Formula
C20H20ClN3O3
Synonyms
  • 5-(p-Chlorophenyl)-1-(p-methoxyphenyl)-N-methylpyrazole-3-propionohydroxamic acid
  • Tepoxalin
  • Tepoxalina
  • Tepoxaline
  • Tepoxaliume
External IDs
  • ORF 20485
  • ORF-20485
  • RWJ 20485
  • RWJ-20485
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbacavirTepoxalin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Tepoxalin.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Tepoxalin is combined with Abciximab.
AcebutololTepoxalin may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Tepoxalin.
Food Interactions
Not Available

Products

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International/Other Brands
Zubrin

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Pyrazoles
Direct Parent
Phenylpyrazoles
Alternative Parents
Methoxyanilines / Phenoxy compounds / Anisoles / Methoxybenzenes / Alkyl aryl ethers / Chlorobenzenes / Aryl chlorides / Heteroaromatic compounds / Hydroxamic acids / Azacyclic compounds
show 6 more
Substituents
Alkyl aryl ether / Anisole / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Chlorobenzene
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrazoles, aromatic ether, monochlorobenzenes, hydroxamic acid (CHEBI:76277)
Affected organisms
Not Available

Chemical Identifiers

UNII
TZ4OX61974
CAS number
103475-41-8
InChI Key
XYKWNRUXCOIMFZ-UHFFFAOYSA-N
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
IUPAC Name
3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N-hydroxy-N-methylpropanamide
SMILES
COC1=CC=C(C=C1)N1N=C(CCC(=O)N(C)O)C=C1C1=CC=C(Cl)C=C1

References

General References
  1. McCarthy RJ: Tepoxalin no longer available commercially. Am J Vet Res. 2013 Jul;74(7):948. doi: 10.2460/ajvr.74.7.948. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. Ritchie DM, Argentieri DC, Aparicio BL, Plante RK, Lau CY, Barbone AG: Cytokine-modulating activity of tepoxalin, a new potential antirheumatic. Int J Immunopharmacol. 1995 Oct;17(10):805-12. [Article]
  5. 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. [Article]
  6. Fusellier M, Desfontis JC, Madec S, Gautier F, Marescaux L, Debailleul M, Gogny M: Effect of tepoxalin on renal function in healthy dogs receiving an angiotensin-converting enzyme inhibitor. J Vet Pharmacol Ther. 2005 Dec;28(6):581-6. [Article]
  7. Bosmans T, Gasthuys F, Duchateau L, de Bruin T, Verhoeven G, Polis I: A comparison of tepoxalin-buprenorphine combination and buprenorphine for postoperative analgesia in dogs: a clinical study. J Vet Med A Physiol Pathol Clin Med. 2007 Sep;54(7):364-9. [Article]
  8. Tam SS, Lee DH, Wang EY, Munroe DG, Lau CY: Tepoxalin, a novel dual inhibitor of the prostaglandin-H synthase cyclooxygenase and peroxidase activities. J Biol Chem. 1995 Jun 9;270(23):13948-55. [Article]
  9. Willburger RE, Wittenberg RH, Schmidt K, Kleemeyer KS, Peskar BA: Antiinflammatory effect of tepoxalin: blood and synovial tissue studied in patients with knee arthrosis. Acta Orthop Scand. 1998 Jun;69(3):295-300. [Article]
  10. 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. [Article]
  11. 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. Epub 2009 Jun 22. [Article]
  12. 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. [Article]
  13. 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. [Article]
  14. Hernandez S, Moreno I, SanMartin R, Gomez G, Herrero MT, Dominguez E: Toward safer processes for C-C biaryl bond construction: catalytic direct C-H arylation and tin-free radical coupling in the synthesis of pyrazolophenanthridines. J Org Chem. 2010 Jan 15;75(2):434-41. doi: 10.1021/jo902257j. [Article]
  15. 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. Epub 2010 Oct 30. [Article]
  16. 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. [Article]
  17. 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. [Article]
  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. [Article]
  19. 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. [Article]
  20. 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. [Article]
  21. 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. [Article]
  22. 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. Epub 2012 Jan 12. [Article]
  23. 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. [Article]
  24. 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. [Article]
  25. 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. Epub 2012 Oct 14. [Article]
  26. 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. [Article]
  27. 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. [Article]
  28. Fung-Leung WP, Pope BL, Chourmouzis E, Panakos JA, Lau CY: Tepoxalin, a novel immunomodulatory compound, synergizes with CsA in suppression of graft-versus-host reaction and allogeneic skin graft rejection. Transplantation. 1995 Aug 27;60(4):362-8. [Article]
KEGG Drug
D06075
KEGG Compound
C18362
ChemSpider
53906
BindingDB
50001183
ChEBI
76277
ChEMBL
CHEMBL316040
ZINC
ZINC000000607214
Wikipedia
Tepoxalin

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00375 mg/mLALOGPS
logP4.01ALOGPS
logP3.44Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)8.53Chemaxon
pKa (Strongest Basic)1.31Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area67.59 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity104.67 m3·mol-1Chemaxon
Polarizability40.75 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-59e0e1607e2758d1b6af
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-053i-1009000000-13ad66bfdabb97bee210
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-5a4cf800c035b14552e6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-093d-0193000000-be9df831b2ee91b218db
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0540-9016000000-4761d452c610bebbc441
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9052000000-6f6628468cd0e09a5b4b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.96857
predicted
DeepCCS 1.0 (2019)
[M+H]+190.32657
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.2888
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:58 / Updated at February 21, 2021 18:53