FIROCOXIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H20O5S
Molecular Weight	336.403
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)OC(=O)C(OCC2CC2)=C1C3=CC=C(C=C3)S(C)(=O)=O

InChI

InChIKey=FULAPETWGIGNMT-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM218719.pdf | http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050387.pdf

Firocoxib is a selective COX-2 inhibitor which was approved by FDA and EMEA for the treatment of osteoarthritis and postoperative pain in dogs (Previcox trade name) and horses (Equioxx trade name). The drug is not for human use.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL4033 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050403.pdf	Inhibitor 8297		0.16 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 157 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050402.pdf	Palliative		Approved 8429	PREVICOX Approved Use For the control of pain and inflammation associated with osteoarthritis and for the control of postoperative pain and inflammation associated with soft-tissue and orthopedic surgery. Launch Date 2008
Postoperative pain 22 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050402.pdf	Primary		Approved 8429	PREVICOX Approved Use For the control of pain and inflammation associated with osteoarthritis and for the control of postoperative pain and inflammation associated with soft-tissue and orthopedic surgery. Launch Date 2008

PubMed

Title	Date	PubMed
In vitro effects and in vivo efficacy of a novel cyclooxygenase-2 inhibitor in dogs with experimentally induced synovitis.	2004 Apr	15077695
In vitro effects and in vivo efficacy of a novel cyclooxygenase-2 inhibitor in cats with lipopolysaccharide-induced pyrexia.	2005 Jul	16111170
Clinical evaluation of firocoxib and carprofen for the treatment of dogs with osteoarthritis.	2006 Oct 21	17056650
The clinical pharmacology of cyclooxygenase-2-selective and dual inhibitors.	2006 Sep	16984827
Efficacy and safety of firocoxib in the management of canine osteoarthritis under field conditions.	2006 Summer	16871495
Clinical effectiveness and safety of a new NSAID, firocoxib: a 1,000 dog study.	2006 Summer	16871494
[European symposium about osteoarthritis in a dog].	2007 Jan 1	17334108
Automated liquid chromatography-tandem mass spectrometry method for the analysis of firocoxib in urine and plasma from horse and dog.	2007 Jun 15	17459786
Firocoxib efficacy preventing urate-induced synovitis, pain, and inflammation in dogs.	2007 Spring	17447224
Switching NSAIDs in practice: insights from the Previcox (firocoxib) Experience Trial.	2007 Winter	18183545
Comparison of the effects of firocoxib, carprofen and vedaprofen in a sodium urate crystal induced synovitis model of arthritis in dogs.	2008 Feb	17408711
Comparison of efficacy and safety of paste formulations of firocoxib and phenylbutazone in horses with naturally occurring osteoarthritis.	2008 Jan 1	18167116
Pharmacokinetics of firocoxib after administration of multiple consecutive daily doses to horses.	2008 Nov	18980421
Effects of firocoxib, meloxicam, and tepoxalin on prostanoid and leukotriene production by duodenal mucosa and other tissues of osteoarthritic dogs.	2008 Sep	18764695
Systematic review of the management of canine osteoarthritis.	2009 Apr 4	19346540
Effect of firocoxib or flunixin meglumine on recovery of ischemic-injured equine jejunum.	2009 Aug	19645580
Confirmatory analysis of firocoxib in bovine milk by rapid resolution liquid chromatography tandem mass spectrometry.	2009 Feb 15	19179123
Effects of firocoxib and tepoxalin on healing in a canine gastric mucosal injury model.	2009 Jan-Feb	19175721
The use of force plate measurements to titrate the dosage of a new COX-2 inhibitor in lame horses.	2009 Mar	19469242
Effect of nonsteroidal anti-inflammatory drugs with varied cyclooxygenase-2 selectivity on cyclooxygenase protein and prostanoid concentrations in pyloric and duodenal mucosa of dogs.	2009 Oct	19795939
The effects of firocoxib (Previcox) in geriatric dogs over a period of 90 days.	2009 Sep	20169752
The effect of doxycycline on canine hip osteoarthritis: design of a 6-months clinical trial.	2009 Sep	19687625
Does administration of non-steroidal anti-inflammatory drug determine morphological changes in adrenal cortex: ultrastructural studies.	2010 Oct	20721677
Effects of firocoxib, meloxicam, and tepoxalin administration on eicosanoid production in target tissues of healthy cats.	2010 Sep	20807147

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage of PREVICOX (firocoxib) for oral administration in dogs is 2.27 mg/lb (5.0 mg/kg) body weight once daily as needed for osteoarthritis and for 3 days as needed for postoperative pain and inflammation associated with soft-tissue and orthopedic surgery. The recommended dosage of EQUIOXX (firocoxib) for oral administration in horses is 0.045 mq/lb (0.1 mg/kg) of body weight once daily for up to 14 days. The recommended dosage of EQUIOXX Injection for intravenous administration in horses is 0.04 mg/lb (0.09 mg/kg) of body weight once daily for up to 5 days.

Route of Administration: Other

In Vitro Use Guide

Equine peripheral blood mononuclear cells were isolated by density gradient centrifugation and incubated at 37C with medium alone, firocoxib (100 ng/mL), LPS (1 ng/mL or 1 ug/mL), or combinations of firocoxib and both LPS concentrations. After 4 hours, supernatants were collected and tested for prostaglandin E2 (PGE2) concentration with an enzyme inhibition assay, and gene expression in cell lysates was measured with PCR assays.

Name

Type

Language

FIROCOXIB

Official Name

English

firocoxib [INN]

Common Name

English

NSC-758895

Code

English

ML-1785713

Code

English

2(5H)-FURANONE, 3-(CYCLOPROPYLMETHOXY)-5,5-DIMETHYL-4-(4-(METHYLSULFONYL)PHENYL)-

Systematic Name

English

FIROCOXIB (EMA EPAR: VETERINARY)

Common Name

English

FIROCOXIB [MART.]

Common Name

English

EQUIOXX

Brand Name

English

FIROCOXIB [GREEN BOOK]

Common Name

English

LIBRENS

Common Name

English

3-(Cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-one

Systematic Name

English

ML-1,785,713

Code

English

PREVICOX

Common Name

English

FIROCOXIB [USAN]

Common Name

English

FIROCOXIB [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323