Firocoxib |
![]() Last updated: 06/09/2025 |
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(Not known by any other names) |
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A non-steroidal anti-inflammatory drug (NSAID) used in veterinary medicine | |
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Used for treating the pain and inflammation associated with arthritis in animals | |
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Dogs; Horses |
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Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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None | |
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C₁₇H₂₀O₅S | |
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CC1(C(=C(C(=O)O1)OCC2CC2)C3=CC=C(C=C3)S(=O)(=O)C)C | |
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No data | |
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FULAPETWGIGNMT-UHFFFAOYSA-N | |
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InChI=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 | |
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Yes |
General status |
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Anti-inflammatory agent, Medicinal drug; Analgesic | |
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Unclassified substance | |
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Synthetic | |
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Inhibits the synthesis of the class of compounds called prostaglandins. Selective cyclooxygenase-2 (COX-2) inhibitor | |
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[Prostaglandin G/H Synthase 2 (COX-2), Antagonist] | |
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189954-96-9 | |
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Musculo-skeletal system: Anti-inflammatory and antirheumatic products | |
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QM01AH90 | |
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No | |
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Allowed substance (Table 1: Equidae) | |
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336.40 | |
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3-(cyclopropylmethoxy)-5,5-dimethyl-4-(4-methylsulfonylphenyl)furan-2-one | |
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Solid |
Commercial |
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Current | |||||||||
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1999, first described in literature; early 2000s, commercially introduced | |||||||||
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Equioxx Solution for Injection | Audevard | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | ||||||
Previcox Chewable tablets for dogs | Boehringer Ingelheim Vetmedica GmbH | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
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Available as tablets, oral pastes and solutions for injection | |||||||||
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The production of firocoxib involves a multi-step synthesis starting with the preparation of key intermediates. One route begins with methylation of p-bromopropiophenone or a Friedel–Crafts acylation of bromobenzene, followed by sulfonation to introduce the sulfonyl group efficiently. A crucial intermediate, 2-(cyclopropylmethoxy)acetic acid, is synthesized via nucleophilic substitution using sodium 2-chloroacetate and cyclopropylmethanol. Separately, the aromatic portion is built through Friedel–Crafts acylation, bromination, hydrolysis, and oxidation steps to yield a methylsulfonylphenyl ketone derivative. These fragments are then coupled and cyclised to form the final furanone ring structure of firocoxib. | |||||||||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Known metabolites |
None
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Terrestrial ecotoxicology |
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> 2000 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
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General |
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High (class III) | - | - | ||||||||
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> 2000 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
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2000 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
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Extensively metabolised and excreta mainly via the urine but with some biliary excretion. In horses elimination half-life after a single dose is approx 1.5 days. | A4 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 4 = Verified data |
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Health issues |
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Possible liver, kidney and thyroid toxicant |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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firocoxib | ||
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Record last updated: | 06/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |