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Flurbiprofen

Flurbiprofen Structure
CAS No.
5104-49-4
Chemical Name:
Flurbiprofen
Synonyms
ANSAID;2-(2-fluorobiphenyl-4-yl)propanoic acid;fp70;ANSIDE;Adfeed;froben;U-27182;Antadys;Cebutid;Stayban
CBNumber:
CB7465967
Molecular Formula:
C15H13FO2
Molecular Weight:
244.27
MOL File:
5104-49-4.mol
MSDS File:
SDS
Modify Date:
2024/8/21 22:41:43

Flurbiprofen Properties

Melting point 110-112 °C(lit.)
Boiling point 376.2±30.0 °C(Predicted)
Density 1.1795 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility methanol: soluble50mg/mL
pka pKa 3.80(H2O) (Uncertain)
form White solid
color white to off-white
Water Solubility 8mg/L(room temperature)
Merck 14,4199
InChIKey SYTBZMRGLBWNTM-UHFFFAOYSA-N
CAS DataBase Reference 5104-49-4(CAS DataBase Reference)
EPA Substance Registry System [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-?-methyl- (5104-49-4)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310+P330-P405-P501
Hazard Codes  T,C
Risk Statements  25-23/24/25
Safety Statements  36/37/39-45
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
RTECS  DU8341000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29163990
NFPA 704
1
3 0

Flurbiprofen price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) F8514 Flurbiprofen cyclooxygenase inhibitor 5104-49-4 1G ₹8172.88 2022-06-14 Buy
Sigma-Aldrich(India) PHR1499 Flurbiprofen Pharmaceutical Secondary Standard; Certified Reference Material 5104-49-4 500MG ₹10792.53 2022-06-14 Buy
Sigma-Aldrich(India) F8514 Flurbiprofen cyclooxygenase inhibitor 5104-49-4 5G ₹27896.03 2022-06-14 Buy
Sigma-Aldrich(India) F8514 Flurbiprofen cyclooxygenase inhibitor 5104-49-4 25G ₹79325.6 2022-06-14 Buy
TCI Chemicals (India) F0371 Flurbiprofen 5104-49-4 5G ₹4800 2022-05-26 Buy
Product number Packaging Price Buy
F8514 1G ₹8172.88 Buy
PHR1499 500MG ₹10792.53 Buy
F8514 5G ₹27896.03 Buy
F8514 25G ₹79325.6 Buy
F0371 5G ₹4800 Buy

Flurbiprofen Chemical Properties,Uses,Production

Description

Flurbiprofen synthesis was originally reported in 1974. During a study of the pharmacological properties of a large number of substituted phenylalkanoic acids, including ibuprofen and ibufenac, the most potent were found to be substituted 2-(4-biphenyl)propionic acids. Further toxicological and pharmacological studies indicated that flurbiprofen possessed the most favorable therapeutic profile, so it was selected for further clinical development. It was not marketed until 1987, when it was introduced as the sodium salt as Ocufen, the first topical NSAID indicated for ophthalmic use in the United States. The indication for Ocufen is the same as that for Profenal—that is, to inhibit intraoperative miosis induced by prostaglandins in cataract surgery.

Chemical Properties

White to Off-White Crystalline Solid

Uses

An anti-inflammatory used as an analgesic.

Indications

Flurbiprofen (Ansaid) is indicated for the treatment of rheumatoid arthritis and osteoarthritis. Its half-life, longer than that of many of the NSAIDs, allows for twice daily dosing.The most common adverse effects of flurbiprofen are similar to those of the other acidic NSAIDs. Flurbiprofen inhibits both COX isoforms about equally.

General Description

Flurbiprofen (Ansaid, Ocufen, Froben), is another drug inthis class indicated for both acute and long-term managementof RA and OA but with a more complex mechanism ofaction. Unlike the other drugs in this class, it does not undergochiral inversion (i.e., the conversion of the “inactive”[R]-enantiomer to the active, [S]-enantiomer). Similar to aspirinand other salicylates, both flurbiprofen enantiomersblock COX-2 induction as well as inhibiting the nuclearfactor-κB-mediated polymorphonuclear leukocyte apoptosissignaling; therefore, both enantiomers are believed to contributeequally to its overall anti-inflammatory action.
(R)-flurbiprofen is actually a strong clinical candidate forthe treatment of Alzheimer disease, because it has beenshown to reduce Aβ42 production by human cells.

Biological Activity

Potent inhibitor of cyclooxygenase (IC 50 values are 0.1 and 0.4 μ M for inhibition of human COX-1 and COX-2 respectively). Analgesic, anti-inflammatory and antipyretic in vivo . Inhibits tumor cell growth in vitro and in vivo . Also inhibits fibroblast proliferation in vitro .

Pharmacokinetics

Flurbiprofen is well absorbed after oral administration, with peak plasma levels being attained within 1.5 hours. Food alters the rate of absorption but not the extent of its bioavailability. It is extensively bound to plasma proteins (99%).and has a plasma half-life of 2 to 4 hours. Metabolism is extensive, with 60 to 70% of flurbiprofen and its metabolites being excreted as sulfate and glucuronide conjugates. Flurbiprofen shows some interesting metabolic patterns, with 40 to 47% as the 4′-hydroxy metabolite, 5% as the 3′,4′-dihydroxy metabolite, 20 to 30% as the 3′-hydroxy- 4′-methoxy metabolite, and the remaining 20 to 25% of the drug being excreted unchanged. None of these metabolites demonstrates significant anti-inflammatory activity.

Clinical Use

Flurbiprofen is indicated as an oral formulation for the acute or long-term treatment of rheumatoid arthritis and osteoarthritis and as an ophthalmic solution for the inhibition of intraoperative miosis.

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