Firocoxib
Identification
- Generic Name
- Firocoxib
- DrugBank Accession Number
- DB09217
- Background
Firocoxib is a cycooxygenase-2 (COX-2) selective non-steroidal anti-inflammatory drug. It currently approved for veterinary use in dogs and horses under the brand names Equioxx and Previcox. Firocoxib was the first COX-2 inhibitor approved by the U.S. Food and Drug Administration for horses. Firocoxib is not intended or approved for use in human medicine.
- Type
- Small Molecule
- Groups
- Experimental, Vet approved
- Structure
Structure for Firocoxib (DB09217)
- Weight
- Average: 336.4
Monoisotopic: 336.103144918 - Chemical Formula
- C17H20O5S
- Synonyms
- Firocoxib
- External IDs
- ML-1,785,713
Pharmacology
- Indication
Used for the treatment of pain inflammation and fever in horses and dogs.
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Not Available
- Mechanism of action
Target Actions Organism UProstaglandin G/H synthase 2 Not Available Humans - 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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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Firocoxib may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Firocoxib is combined with Abciximab. Acebutolol Firocoxib may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Firocoxib. Acemetacin The risk or severity of adverse effects can be increased when Firocoxib is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Firocoxib is combined with Acenocoumarol. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Firocoxib. Acetohexamide The protein binding of Acetohexamide can be decreased when combined with Firocoxib. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Firocoxib. Aclidinium Firocoxib may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
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- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonyl compounds
- Direct Parent
- Benzenesulfonyl compounds
- Alternative Parents
- Butenolides / Sulfones / Enoate esters / Lactones / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 2-furanone / Alpha,beta-unsaturated carboxylic ester / Aromatic heteromonocyclic compound / Benzenesulfonyl group / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dihydrofuran / Enoate ester / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfone, butenolide, cyclopropanes, enol ether (CHEBI:76136)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Y6V2W4S4WT
- CAS number
- 189954-96-9
- InChI Key
- FULAPETWGIGNMT-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 3-(cyclopropylmethoxy)-4-(4-methanesulfonylphenyl)-5,5-dimethyl-2,5-dihydrofuran-2-one
- SMILES
- CC1(C)OC(=O)C(OCC2CC2)=C1C1=CC=C(C=C1)S(C)(=O)=O
References
- General References
- Not Available
- External Links
- KEGG Drug
- D03712
- KEGG Compound
- C18363
- PubChem Compound
- 208910
- PubChem Substance
- 310265124
- ChemSpider
- 181008
- BindingDB
- 50080082
- 473298
- ChEBI
- 76136
- ChEMBL
- CHEMBL69998
- ZINC
- ZINC000003623447
- PharmGKB
- PA166049194
- Wikipedia
- Firocoxib
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0105 mg/mL ALOGPS logP 2.98 ALOGPS logP 1.96 ChemAxon logS -4.5 ALOGPS pKa (Strongest Acidic) 19.69 ChemAxon pKa (Strongest Basic) -5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 69.67 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 87.35 m3·mol-1 ChemAxon Polarizability 35.11 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- McCann ME, Andersen DR, Zhang D, Brideau C, Black WC, Hanson PD, Hickey GJ: In vitro effects and in vivo efficacy of a novel cyclooxygenase-2 inhibitor in dogs with experimentally induced synovitis. Am J Vet Res. 2004 Apr;65(4):503-12. [Article]
Drug created on October 21, 2015 16:53 / Updated on February 21, 2021 18:52