Firocoxib

Identification

Name
Firocoxib
Accession Number
DB09217
Type
Small Molecule
Groups
Experimental, Vet approved
Description

Firocoxib (INN; brand names Equioxx and Previcox) is a non-steroidal anti-inflammatory drug of the COX-2 inhibitor (coxib) class, currently approved for use in dogs and horses. 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.

Structure
Thumb
Synonyms
  • firocoxib
External IDs
ML-1,785,713
Categories
UNII
Y6V2W4S4WT
CAS number
189954-96-9
Weight
Average: 336.4
Monoisotopic: 336.103144918
Chemical Formula
C17H20O5S
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

Pharmacology

Indication

Used for the treatment of pain inflammation and fever in horses and dogs.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 2Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Firocoxib is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Firocoxib is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Firocoxib is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Firocoxib.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Firocoxib.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Firocoxib is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of hypertension can be increased when 3,4-Methylenedioxyamphetamine is combined with Firocoxib.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Firocoxib.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Firocoxib is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Firocoxib.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D03712
KEGG Compound
C18363
PubChem Compound
208910
PubChem Substance
310265124
ChemSpider
181008
BindingDB
50080082
ChEBI
76136
ChEMBL
CHEMBL69998
PharmGKB
PA166049194
Wikipedia
Firocoxib

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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
Benzenesulfonyl group / 2-furanone / Dihydrofuran / Sulfone / Sulfonyl / Enoate ester / Alpha,beta-unsaturated carboxylic ester / Lactone / Carboxylic acid ester / Carboxylic acid derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfone, butenolide, cyclopropanes, enol ether (CHEBI:76136)

Targets

Kind
Protein
Organism
Human
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. [PubMed:15077695]

Drug created on October 21, 2015 10:53 / Updated on November 02, 2018 07:00