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
Thumb
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.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 2Not AvailableHumans
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
Adverseeffects
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Toxicity

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.
DrugInteraction
AbacavirFirocoxib may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Firocoxib is combined with Abciximab.
AcebutololFirocoxib may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Firocoxib.
AcemetacinThe risk or severity of adverse effects can be increased when Firocoxib is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Firocoxib is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Firocoxib.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Firocoxib.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Firocoxib.
AclidiniumFirocoxib may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Interactions
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Food Interactions
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
KEGG Drug
D03712
KEGG Compound
C18363
PubChem Compound
208910
PubChem Substance
310265124
ChemSpider
181008
BindingDB
50080082
RxNav
473298
ChEBI
76136
ChEMBL
CHEMBL69998
ZINC
ZINC000003623447
PharmGKB
PA166049194
Wikipedia
Firocoxib

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0105 mg/mLALOGPS
logP2.98ALOGPS
logP1.96ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.69ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity87.35 m3·mol-1ChemAxon
Polarizability35.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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
  1. 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