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Merck

F8514

Flurbiprofen

cyclooxygenase inhibitor

Synonyme(s) :

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

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A propos de cet article

Formule linéaire :
C6H5C6H3(F)CH(CH3)CO2H
Numéro CAS:
5104-49-4
Poids moléculaire :
244.26
NACRES:
NA.76
PubChem Substance ID:
24894968
UNSPSC Code:
51102829
EC Number:
225-827-6
MDL number:
MFCD00079303

Principaux documents

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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

SMILES string

CC(C(O)=O)c1ccc(c(F)c1)-c2ccccc2

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

Quality Level

100

Gene Information

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

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Catégories apparentées

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

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Classe de stockage

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

ppe

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCT5704
MKCP0624
MKCS4587
MKCJ8359
MKBX6049V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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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