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F8514 Sigma-Aldrich

Flurbiprofen

cyclooxygenase inhibitor

Synonym: (±)-2-Fluoro-α-methyl-4-biphenylacetic acid, L-790,330

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Properties

Related Categories A to C, Antibiotics, Antibiotics A to Z, Antibiotics  A-F, Application Index,
Quality Level   100
biological source   synthetic
assay   ≥98.5% (HPLC)
form   powder
color   white to off-white
mp   110-112 °C (lit.)
solubility   methanol: 50 mg/mL
Mode of action   enzyme | inhibits
antibiotic activity spectrum   fungi
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.

Packaging

1, 5, 25 g in poly bottle

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 & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
DU8341000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

The Role of Inflammation in Neurodegeneration

It is well established that the brain can sense and react to peripheral insults through the rapid induction of fever and other neuroendocrine changes in response to events such as infection and tissu...
Scott Hauser, Technology Transfer Specialist, Sigma® Life Science
Biofiles, Vol. 8, No. 19
Keywords: Adhesion, Central Nervous System, Diseases, Gene expression, Inflammation, Neurodegenerative Diseases, Reductions

Peer-Reviewed Papers
15

References

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