Ugrás a tartalomra
Merck

F8514

Sigma-Aldrich

Flurbiprofen

cyclooxygenase inhibitor

Szinonimák:

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

Bejelentkezésa Szervezeti és Szerződéses árazás megtekintéséhez


About This Item

Lineáris képlet:
C6H5C6H3(F)CH(CH3)CO2H
CAS-szám:
Molekulatömeg:
244.26
EC-szám:
MDL-szám:
UNSPSC kód:
51102829
PubChem Substance ID:
NACRES:
NA.76

biológiai forrás

synthetic

Minőségi szint

Teszt

≥98.5% (HPLC)

Forma

powder

szín

white to off-white

mp

110-112 °C (lit.)

oldhatóság

methanol: 50 mg/mL

antibiotikus hatásspektrum

fungi

Hatásmechanizmus

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)

Nemzetközi kémiai azonosító kulcs

SYTBZMRGLBWNTM-UHFFFAOYSA-N

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Alkalmazás

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.

Biokémiai/fiziológiai hatások

Cyclooxygenase (COX) inhibitor; non-steroidal anti-inflammatory agent with antifungal activity. 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.
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.

Piktogramok

Skull and crossbones

Figyelmeztetés

Danger

Figyelmeztető mondatok

Óvintézkedésre vonatkozó mondatok

Veszélyességi osztályok

Acute Tox. 3 Oral

Tárolási osztály kódja

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

WGK

WGK 3

Lobbanási pont (F)

Not applicable

Lobbanási pont (C)

Not applicable

Egyéni védőeszköz

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


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Analitikai tanúsítványok (COA)

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Az ügyfelek ezeket is megtekintették

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
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
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
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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