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F8514

Sigma-Aldrich

Flurbiprofen

cyclooxygenase inhibitor

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Synonym(s):
(±)-2-Fluoro-α-methyl-4-biphenylacetic acid, L-790,330
Linear Formula:
C6H5C6H3(F)CH(CH3)CO2H
CAS Number:
Molecular Weight:
244.26
EC Number:
MDL number:
PubChem Substance ID:

biological source

synthetic

Quality Level

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

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This Item
PHR1499F0285200Y0002271
Flurbiprofen cyclooxygenase inhibitor

Sigma-Aldrich

F8514

Flurbiprofen

Flurbiprofen Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1499

Flurbiprofen

Flurbiprofen European Pharmacopoeia (EP) Reference Standard

F0285200

Flurbiprofen

assay

≥98.5% (HPLC)

assay

-

assay

-

assay

-

form

powder

form

-

form

-

form

-

color

white to off-white

color

-

color

-

color

-

mp

110-112 °C (lit.)

mp

110-112 °C (lit.)

mp

110-112 °C (lit.)

mp

110-112 °C (lit.)

solubility

methanol: 50 mg/mL

solubility

-

solubility

-

solubility

-

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

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

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Jessica Amadio et al.
Applied and environmental microbiology, 76(18), 6299-6303 (2010-07-27)
The biotransformation of the fluorinated anti-inflammatory drug flurbiprofen was investigated in Cunninghamella spp. Mono- and dihydroxylated metabolites were detected using gas chromatography-mass spectrometry and fluorine-19 nuclear magnetic resonance spectroscopy, and the major metabolite 4'-hydroxyflurbiprofen was isolated by preparative high-pressure liquid
T Mahmud et al.
Gut, 43(6), 775-782 (1998-11-21)
Non-steroidal anti-inflammatory drugs (NSAIDs) cause gastrointestinal damage by a non-prostaglandin (PG) dependent "topical" action and by inhibiting cyclooxygenase. To discriminate between these two effects by studying some key pathophysiological steps in NSAID enteropathy following administration of (R)- and (S)-flurbiprofen, the
N M Davies
Clinical pharmacokinetics, 28(2), 100-114 (1995-02-01)
Flurbiprofen is a chiral nonsteroidal anti-inflammatory drug (NSAID) of the 2-arylpropionic acid class. Although it possesses a chiral centre, with the S-(+)-enantiomer possessing most of the beneficial anti-inflammatory activity, both enantiomers may possess analgesic activity and all flurbiprofen preparations to
Mirco Govoni et al.
The Journal of pharmacology and experimental therapeutics, 346(1), 96-104 (2013-04-19)
Liver first-pass metabolism differs considerably among organic nitrates, but little information exists on the mechanism of denitration of these compounds in hepatic tissue. The metabolism of nitrooxybutyl-esters of flurbiprofen and ferulic-acid, a class of organic nitrates with potential therapeutic implication
Structural and functional basis of cyclooxygenase inhibition.
Anna L Blobaum et al.
Journal of medicinal chemistry, 50(7), 1425-1441 (2007-03-08)

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