F8514

Flurbiprofen

cyclooxygenase inhibitor

• Synonym(s): (±)-2-Fluoro-α-methyl-4-biphenylacetic acid, L-790,330
• Linear Formula: C₆H₅C₆H₃(F)CH(CH₃)CO₂H
• CAS Number: 5104-49-4
• Molecular Weight: 244.26
• EC Number: 225-827-6
• MDL number: MFCD00079303
• UNSPSC Code: 51102829
• PubChem Substance ID: 24894968
• NACRES: NA.76

Properties

• biological source: synthetic
• Assay: ≥98.5% (HPLC)
• form: powder
• color: white to off-white
• mp: 110-112 °C (lit.)
• solubility: methanol: 50 mg/mL
• antibiotic activity spectrum: fungi
• Mode of action: enzyme | inhibits
• SMILES string: CC(C(O)=O)c1ccc(c(F)c1)-c2ccccc2
• InChI: 1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)
• InChI key: SYTBZMRGLBWNTM-UHFFFAOYSA-N
• Gene Information: human ... ALB(213) , APP(351) , CYP1A2(1544) , CYP2C9(1559) , PTGS1(5742) , PTGS2(5743) ; rat ... Ptgs1(24693)

Description

Application

Flurbiprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic, analgesic, and antifungal activity. Oral formulations of flurbiprofen may be used to treat rheumatoid arthritis, osteoarthritis and anklylosing spondylitis. Flurbiprofen is also used topically during ocular surgery to prevent or reduce intraoperative miosis. Flurbiprofen is structurally and pharmacologically related to ibuprofen. It is used to study the pathophysiological steps of NSAID enteropathy in the rat and the biotransformation of flurbiprofen by Cunninghamella species.

Biochem/physiol Actions

Fluibiprofen is a cyclooxygenase (COX) inhibitor, which is an enzyme responsible for the conversion of arachidonic acid to prostaglandin G2 (PGG2) and PGG2 to prostaglandin H2 (PGH2) in the prostaglandin synthesis pathway. This decreases the prostaglandins which cause inflammation, pain, swelling and fever. Flurbiprofen inhibits the activity of both COX-1 and -2. The S enantiomer inhibits prostaglandin synthesis and has both anti-inflammatory and analgesic activity, while the R enantiomer does not inhibit prostaglandin synthesis and displays only analgesic activity.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves