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F8514

Sigma-Aldrich

Flurbiprofen

cyclooxygenase inhibitor

Synonim(y):

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

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About This Item

Wzór liniowy:
C6H5C6H3(F)CH(CH3)CO2H
Numer CAS:
5104-49-4
Masa cząsteczkowa:
244.26
Numer WE:
225-827-6
Numer MDL:
MFCD00079303
Kod UNSPSC:
51102829
Identyfikator substancji w PubChem:
24894968
NACRES:
NA.76

pochodzenie biologiczne

synthetic

Próba

≥98.5% (HPLC)

Postać

powder

kolor

white to off-white

mp

110-112 °C (lit.)

rozpuszczalność

methanol: 50 mg/mL

spektrum działania antybiotyku

fungi

Tryb działania

enzyme | inhibits

ciąg SMILES

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)

Klucz InChI

SYTBZMRGLBWNTM-UHFFFAOYSA-N

informacje o genach

human ... ALB(213) , APP(351) , CYP1A2(1544) , CYP2C9(1559) , PTGS1(5742) , PTGS2(5743)
rat ... Ptgs1(24693)

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Zastosowanie

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.

Działania biochem./fizjol.

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.
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Piktogramy

Skull and crossbones
GHS06

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H301

Zwroty wskazujące środki ostrożności

P264 - P270 - P301 + P310 - P405 - P501

Klasyfikacja zagrożeń

Acute Tox. 3 Oral

Kod klasy składowania

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certyfikaty analizy (CoA)

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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
Jack U Flanagan et al.
PloS one, 7(8), e43965-e43965 (2012-09-01)
Aldo-keto reductase 1C3 (AKR1C3) catalyses the NADPH dependent reduction of carbonyl groups in a number of important steroid and prostanoid molecules. The enzyme is also over-expressed in prostate and breast cancer and its expression is correlated with the aggressiveness of
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