Firocoxib
[CAS# 189954-96-9]

Identification

• Classification: Analytical chemistry >> Standard >> Forensic and veterinary standards
• Name: Firocoxib
• Synonyms: 3-(Cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone
• Molecular Formula: C₁₇H₂₀O₅S
• Molecular Weight: 336.40
• CAS Registry Number: 189954-96-9
• EC Number: 837-109-5
• SMILES: CC1(C(=C(C(=O)O1)OCC2CC2)C3=CC=C(C=C3)S(=O)(=O)C)C

Properties

• Solubility: 100mM (DMSO), 20mM (ethanol)
• Density: 1.31

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H360-H360D-H361-H373-H412
• Safety Statements: P203-P260-P273-P280-P318-P319-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	2	H361
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Reproductive toxicity	Repr.	1B	H360

Discovery and Applications

Firocoxib is a selective non-steroidal anti-inflammatory drug (NSAID) that belongs to the class of cyclooxygenase-2 (COX-2) inhibitors. It was developed primarily for veterinary use, particularly in dogs and horses, to manage pain and inflammation associated with osteoarthritis and post-operative pain. The discovery of firocoxib traces back to the late 1990s, during a period when pharmaceutical companies were focusing on developing COX-2 selective inhibitors that would minimize gastrointestinal side effects commonly associated with traditional NSAIDs.

The compound was discovered by a research team at Merck & Co., who aimed to create a more targeted anti-inflammatory agent. In 2003, firocoxib was approved by the U.S. Food and Drug Administration (FDA) for use in dogs under the brand name Previcox. Its selectivity for the COX-2 enzyme allows it to effectively reduce pain and inflammation while sparing COX-1, which is responsible for protecting the gastric mucosa and maintaining renal blood flow. This selectivity results in a more favorable safety profile compared to non-selective NSAIDs.

Firocoxib is primarily administered orally and is available in chewable tablet form for dogs, making it easy for pet owners to provide medication to their animals. The drug is used to treat conditions such as osteoarthritis, which is prevalent in older dogs, and to alleviate pain following surgical procedures. The rapid onset of action and extended duration of effect make firocoxib a valuable option in managing chronic pain in veterinary medicine.

In addition to its application in veterinary medicine, firocoxib has been the subject of research for potential use in human medicine. Studies have investigated its efficacy in treating pain and inflammation in conditions such as arthritis, although it is not currently approved for human use. The continued exploration of firocoxib and its analogs reflects the ongoing interest in developing safer and more effective anti-inflammatory medications.

Research also focuses on understanding the molecular mechanisms underlying the selective inhibition of COX-2 by firocoxib. This understanding could lead to the development of new compounds with improved efficacy and safety profiles. The ongoing study of firocoxib emphasizes its significance in both veterinary and potential human therapeutic contexts, reinforcing the importance of COX-2 inhibitors in pain management.

References

2023. Therapeutic Target Database describing target druggability information. Nucleic Acids Research, .
DOI: 10.1093/nar/gkad751

2023. Pharmacokinetics and effect on renal function and average daily gain in lambs after castration and tail docking, of firocoxib and meloxicam. New Zealand Veterinary Journal, .
DOI: 10.1080/00480169.2023.2232337