Firocoxib

{{Short description|COX-2 selective NSAID veterinary drug}}

{{Use American English|date=August 2022}}

{{Use dmy dates|date=February 2024}}

{{Infobox drug

| Verifiedfields = changed

| verifiedrevid = 443742691

| image = Firocoxib.svg

| image_class = skin-invert-image

| alt =

| image2 = Firocoxib-3D-spacefill.png

| alt2 = Firocoxib molecule

| pronounce =

| tradename = Equioxx, Previcox

| Drugs.com = {{ubl

| {{drugs.com|vet|firocoxib-tablets-for-horses}}

| {{drugs.com|vet|firocoxib-chewable-tablets-for-dogs}}

}}

| MedlinePlus =

| DailyMedID = Firocoxib

| pregnancy_AU =

| pregnancy_AU_comment =

| pregnancy_category =

| routes_of_administration = By mouth

| class =

| ATCvet = yes

| ATC_prefix = M01

| ATC_suffix = AH90

| ATC_supplemental =

| legal_AU = S4

| legal_AU_comment =

| legal_BR =

| legal_BR_comment =

| legal_CA = Rx-only

| legal_CA_comment = {{cite web | title=Product information | website=Health Canada | date=22 October 2009 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=99085 | access-date=9 February 2024}}

| legal_DE =

| legal_DE_comment =

| legal_NZ =

| legal_NZ_comment =

| legal_UK = POM

| legal_UK_comment =

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Equioxx- firocoxib tablet, chewable | website=DailyMed | date=14 July 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3f891a61-ce58-4cc1-97e2-a161907ea8eb | access-date=2 August 2022 | archive-date=3 August 2022 | archive-url=https://web.archive.org/web/20220803063530/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3f891a61-ce58-4cc1-97e2-a161907ea8eb | url-status=live }}{{cite web | title=Equioxx- firocoxib paste | website=DailyMed | date=24 February 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=17db1d7d-3683-4030-9039-296a882cc072 | access-date=2 August 2022 | archive-date=3 August 2022 | archive-url=https://web.archive.org/web/20220803063531/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=17db1d7d-3683-4030-9039-296a882cc072 | url-status=live }}{{cite web | title=Previcox- firocoxib tablet, chewable | website=DailyMed | date=23 July 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e6d96ec6-04a4-4986-ac9d-82aa79b28bd4 | access-date=2 August 2022 | archive-date=3 August 2022 | archive-url=https://web.archive.org/web/20220803063530/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e6d96ec6-04a4-4986-ac9d-82aa79b28bd4 | url-status=live }}

| legal_EU = Rx-only

| legal_EU_comment = {{cite web | title=Equioxx EPAR | website=European Medicines Agency (EMA) | date=30 June 2008 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/equioxx | access-date=2 August 2022 | archive-date=25 April 2022 | archive-url=https://web.archive.org/web/20220425005842/https://www.ema.europa.eu/en/medicines/veterinary/EPAR/equioxx | url-status=live }}{{cite web | title=Previcox EPAR | website=European Medicines Agency (EMA) | date=16 March 2007 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/previcox | access-date=2 August 2022 | archive-date=31 July 2021 | archive-url=https://web.archive.org/web/20210731052019/https://www.ema.europa.eu/en/medicines/veterinary/EPAR/previcox | url-status=live }}{{cite web | title=Coxatab EPAR | website=European Medicines Agency (EMA) | date=17 June 2022 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/coxatab | access-date=9 February 2024}}{{cite web | title=Previcox PI | website=Union Register of medicinal products | date=15 September 2004 | url=https://ec.europa.eu/health/documents/community-register/html/v045.htm | access-date=26 December 2024}}

| legal_UN =

| legal_UN_comment =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 189954-96-9

| CAS_supplemental =

| PubChem = 208910

| IUPHAR_ligand =

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB09217

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 181008

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Y6V2W4S4WT

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03712

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 76136

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 69998

| NIAID_ChemDB =

| PDB_ligand =

| synonyms =

| IUPAC_name = 3-(Cyclopropylmethoxy)-5,5-dimethyl-4-(4-methylsulfonylphenyl)furan-2-one

| C=17 | H=20 | O=5 | S=1

| SMILES = O=C2OC(C(=C2\OCC1CC1)\c3ccc(cc3)S(=O)(=O)C)(C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C17H20O5S/c1-17(2)14(12-6-8-13(9-7-12)23(3,19)20)15(16(18)22-17)21-10-11-4-5-11/h6-9,11H,4-5,10H2,1-3H3

| StdInChI_comment =

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FULAPETWGIGNMT-UHFFFAOYSA-N

| density =

| density_notes =

| melting_point =

| melting_high =

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| specific_rotation =

}}

Firocoxib, sold under the brand names Equioxx and Previcox among others, is a nonsteroidal anti-inflammatory drug of the COX-2 inhibitor (coxib) class, approved for use in horses (Equioxx) and for use in dogs (Previcox).{{cite journal | vauthors = Rangel-Nava A, Ramírez-Uribe JM, Recillas-Morales S, Ibancovichi-Camarillo JA, Venebra-Muñoz A, Sánchez-Aparicio P | title = Pharmacological Regulation in the USA and Pharmacokinetics Parameters of Firocoxib, a Highly Selective Cox-2, by Pain Management in Horses | journal = Journal of Equine Veterinary Science | volume = 77 | issue = | pages = 36–42 | date = June 2019 | pmid = 31133314 | doi = 10.1016/j.jevs.2019.02.007 | s2cid = 86530623 }} Firocoxib was the first COX-2 inhibitor approved by the U.S. Food and Drug Administration for horses.{{cite web | url = http://www.thehorse.com/ViewArticle.aspx?ID=9896 | title = New NSAID Equioxx (firocoxib) Approved by USEF | date = 2 July 2007 | access-date = 18 April 2008 | work = The Horse | archive-date = 18 May 2011 | archive-url = https://web.archive.org/web/20110518185548/http://www.thehorse.com/ViewArticle.aspx?ID=9896 | url-status = live }} Firocoxib is not intended or approved for use in human medicine.[http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/veterinary/000142/WC500065936.pdf Equioxx] {{Webarchive|url=https://web.archive.org/web/20141221071942/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/veterinary/000142/WC500065936.pdf |date=21 December 2014 }}, European Medicines Agency (EMA)

Firocoxib, manufactured by Merial, was approved for veterinary use in the United States for dogs in July 2004, and for horses in July 2007, as an oral paste (Equioxx) and July 2016, as tablets.{{Cite web |date=1 July 2007 |title=Merial launches first firocoxib for horses |url=https://www.dvm360.com/view/merial-launches-first-firocoxib-horses |access-date=3 October 2023 |website=DVM 360 }}

Firocoxib is also available as a generic medication for horses{{cite web | title=FDA Approves the First Generic Firocoxib Tablets for Horses | website=U.S. Food and Drug Administration (FDA) | date=1 August 2022 | url=https://www.fda.gov/animal-veterinary/cvm-updates/fda-approves-first-generic-firocoxib-tablets-horses | access-date=2 August 2022 | archive-date=3 August 2022 | archive-url=https://web.archive.org/web/20220803051550/https://www.fda.gov/animal-veterinary/cvm-updates/fda-approves-first-generic-firocoxib-tablets-horses | url-status=live }} and for dogs.{{cite web | title=FDA Approves the First Generic Firocoxib Tablets for Dogs | website=U.S. Food and Drug Administration | date=7 June 2022 | url=https://www.fda.gov/animal-veterinary/cvm-updates/fda-approves-first-generic-firocoxib-chewable-tablets-dogs | access-date=2 August 2022 | archive-date=3 August 2022 | archive-url=https://web.archive.org/web/20220803052501/https://www.fda.gov/animal-veterinary/cvm-updates/fda-approves-first-generic-firocoxib-chewable-tablets-dogs | url-status=live }}