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F8514

Sigma-Aldrich

Flurbiprofen

cyclooxygenase inhibitor

Synonym(s):

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

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About This Item

Linear Formula:
C6H5C6H3(F)CH(CH3)CO2H
CAS Number:
Molecular Weight:
244.26
EC Number:
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.76

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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

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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[1] and the biotransformation of flurbiprofen by Cunninghamella species[2].

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

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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Hoang Anh Nguyen et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 810(1), 77-83 (2004-09-11)
Liquid chromatography with a column-switching technique was developed for simultaneous direct quantification of levofloxacin, gatifloxacin and moxifloxacin in human serum. Serum samples were injected on a LiChroCART 4-4 pre-column (PC) filled with a LiChrospher 100 RP-18, 5 microm where fluoroquinolones
Tânia M G Almeida et al.
Chemistry & biodiversity, 2(12), 1691-1700 (2006-12-29)
Absorption, distribution, metabolism, and excretion (ADME) properties are of invaluable importance to a bioactive compound. Permeation process is one of the most widely studied by many different techniques. Among them, reversed-phase liquid chromatography (RP-LC) is proving to be of great
Zhongping John Lin et al.
Journal of pharmaceutical and biomedical analysis, 37(4), 757-762 (2005-03-31)
A highly sensitive method was developed and validated for determining the free fraction of flunarizine in human plasma. Equilibrium dialysis was used for the separation of free (unbound) drug and liquid chromatography/tandem mass spectrometry (LC-MS/MS) was used for quantitation. Post-dialysis
Konstantinos Petritis et al.
Journal of chromatography. A, 957(2), 173-185 (2002-07-13)
The single run analysis of 23 small peptides (principally glycyl and lysyl dipeptides) is performed by ion-pair reversed-phase liquid chromatography coupled with evaporative light scattering detection or electrospray (tandem) mass spectrometry. Several perfluorinated carboxylic acid homologues are evaluated with an
Cinzia Stella et al.
Journal of separation science, 28(17), 2350-2362 (2005-12-14)
An RPLC was developed to rapidly determine lipophilicity of neutral and basic compounds using three base deactivated RPLC stationary phases particularly designed for the analysis of basic compounds, namely, Supelcosil ABZ(+)Plus, Discovery RP Amide C16, and Zorbax Extend C18. The

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