(S)-Flurbiprofen

ChemicalBook > CAS DataBase List > (S)-Flurbiprofen

Product Name: (S)-Flurbiprofen
CAS No.: 51543-39-6
Chemical Name: (S)-Flurbiprofen
Synonyms: CS-1959;C1sH13FO2;d-Flurbiprofen;Esflurbiprofen;Dexflurbiprofen;(S)-FLURBIPROFEN;(+)-Flurbiprofen;(S)-2-Flurbiprofen;(S)-(+)-FLURBIPROFEN;Flurbiprofen (S)-Isomer
CBNumber: CB8284910
Molecular Formula: C15H13FO2
Formula Weight: 244.26
MOL File: 51543-39-6.mol

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(S)-Flurbiprofen Property

Melting point:: 109-110 °C(lit.)
Boiling point:: 376.2±30.0 °C(Predicted)
Density: 1.199±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: insoluble in H2O; ≥10.9 mg/mL in DMSO; ≥69.1 mg/mL in EtOH
form: A crystalline solid
pka: 4.14±0.10(Predicted)
color: White to off-white

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Safety

Hazard Codes: T
Risk Statements: 25
Safety Statements: 36/37/39-45
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 10004207
Product name: (S)-Flurbiprofen
Purity: ≥99%
Packaging: 100mg
Price: $97
Updated: 2024/03/01

Cayman Chemical

Product number: 10004207
Product name: (S)-Flurbiprofen
Purity: ≥99%
Packaging: 250mg
Price: $231
Updated: 2024/03/01

Cayman Chemical

Product number: 10004207
Product name: (S)-Flurbiprofen
Purity: ≥99%
Packaging: 500mg
Price: $437
Updated: 2024/03/01

Cayman Chemical

Product number: 10004207
Product name: (S)-Flurbiprofen
Purity: ≥99%
Packaging: 1g
Price: $776
Updated: 2024/03/01

TRC

Product number: F598735
Product name: (S)-Flurbiprofen
Packaging: 5g
Price: $1130
Updated: 2021/12/16

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(S)-Flurbiprofen Chemical Properties,Usage,Production

Description

Marketed by Taisho Pharmaceutical Holdings Co., Ltd., and Teijin Pharma Ltd., the (S)-enantiomer of flurbiprofen (named Esflurbiprofen) was approved as a new drug by the PMDA of Japan in 2015. (S)- Flurbiprofen, a cyclooxygenase (COX)-inhibiting nonsteroidal anti-inflammatory (NSAID) drug, is formulated with mentha oil and administered by way of a patch as a treatment for osteoarthritis in the current invention. Interestingly, the (R)- enantiomer is responsible for minimal COX inhibition but has been implicated as a possible treatment for a variety of other diseases. Synthetic approaches to racemic flurbiprofen have been reported in the chemical literature as early as the 1960s, and the mixture was approved as a drug in the United States by the FDA in 1988, marketed by Pharmacia and Upjohn. Toward this end, the current patent estate defines the utility of the active S-enantiomer, and synthetic approaches therein apply to this enantiomer only.

Description

(S)-Flurbiprofen is the COX-active enantiomer of the non-selective COX inhibitor flurbiprofen with IC₅₀ values of 0.48 and 0.47 μM for COX-1 and COX-2, respectively, in guinea pig whole blood. It inhibits the release of 6-keto prostaglandin F_1α (6-keto-PGF_1α; ) and thromboxane B₂ (TXB₂; ) from rat whole blood, gastric mucosa, lung, and jejunal tissue ex vivo in a dose-dependent manner. (S)-Flurbiprofen (1 nM) inhibits basal and bradykinin-, serotonin-, and histamine-stimulated prostaglandin E₂ (PGE₂) release from isolated skin flaps of rat lower hind paws. It also inhibits release of the neuroinflammatory marker calcitonin gene-related peptide (CGRP; Item Nos. 24405 | 24725 | 24728) when used at a concentration of 1 μM. In vivo, (S)-flurbiprofen reduces the number of flinches per minute in the formalin test in rats, indicating antinociceptive activity.

Uses

(S)-Flurbiprofen is the S-isomer of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic.

Definition

ChEBI: (S)-flurbiprofen is a flurbiprofen. It is an enantiomer of a (R)-flurbiprofen.

Synthesis

The synthesis began with conversion of commercially available aniline 168 to racemic flurbiprofen (169) through a Sandmeyer reaction and subsequent phenyl group introduction through the use of sodium tetraphenylborate. A chiral resolution was then performed on the resulting stereogenic acid on multikilogram scale by treatment with (S)- 1-phenylethylamine in MeOH/toluene, which gave various yields of salt 170 as reported by the authors. Acidification with aqueous HCl delivered (S)-flurbiprofen (XXI). Importantly, with respect to green chemistry considerations, the (R)- enantiomer could be recycled by racemizing the undesired (R)- enantiomer 171 in refluxing methanolic sulfuric acid, improving the overall atom economy of the process and significantly reducing waste.

in vitro

it was found that the ic50 value of (s)-flurbiprofen was about 0.5 μm for both cox-1 and cox-2 in guinea pig whole blood [1].

in vivo

the efficacy of multiple applications of s(+)-flurbiprofen plaster (sfpp) was evaluated for the alleviation of inflammatory pain and edema in rat adjuvant-induced arthritis model. multiple applications of sfpp could exert a significant analgesic effect from the first day of application as compared to the other nsaid drugs. in terms of paw edema, sfpp could decrease edema from the second day after application. moreover, multiple applications of sfpp were found to be superior to those of other nsaid drugs in terms of the analgesic effect [2].

IC 50

0.5 μm for both cox-1 and cox-2 in guinea pig whole blood

References

[1] barnett, j. ,chow, j.,ives, d., et al. purification, characterization and selective inhibition of human prostaglandin g/h synthase 1 and 2 expressed in the baculovirus system. biochimica et biophysica acta 1209, 130-139 (1994).
[2] sugimoto m et al. topical anti-inflammatory and analgesic effects of multiple applications of s(+)-flurbiprofen plaster (sfpp) in a rat adjuvant-induced arthritis model. drug dev res. 2016 jun;77(4):206-11.
[3] yataba i, otsuka n, matsushita i, matsumoto h, hoshino y. the efficacy and safety of s-flurbiprofen plaster in the treatment of knee osteoarthritis: a phase ii, randomized, double-blind, placebo-controlled, dose-finding study. j pain res. 2017 apr 11;10:867-880.

(S)-Flurbiprofen Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (S)-Flurbiprofen manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: (S)-Flurbiprofen 51543-39-6
Price: US $0.00-0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 10g
Release date: 2024-05-09

Shaanxi Dideu New Materials Co. Ltd

Product: (S)-Flurbiprofen 51543-39-6
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98.0%
Supply Ability: 10000KGS
Release date: 2024-11-19

Dideu Industries Group Limited

Product: (S)-Flurbiprofen 51543-39-6
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons Min
Release date: 2021-06-15

51543-39-6, (S)-FlurbiprofenRelated Search:

2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID (FLURBIPROFEN),2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID Olaparib Anistreplasa [INN-Spanish] Acipimox Aprepitant Obeticholic Acid Flibaserin 2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID (R)-2-Flurbiprofen (S)-Flurbiprofen 3-Fluoro-4-methylphenylacetic acid 4-Biphenylacetic acid 3-Fluorophenylacetic acid 3-FLUORO-4-METHYLPHENETHYL ALCOHOL (2-FLUORO-4-BIPHENYL)ACETIC ACID alpha-Methyl-4-biphenylacetic acid 5-Fluoro-alpha-methyl-3-biphenylacetic acid 4'-Chloro-5-fluoro-alpha-methyl-3-biphenylacetic acid

(S)-(+)-FLURBIPROFEN

(S)-FLURBIPROFEN

(S)-(+)-2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID

Esflurbiprofen

(S)-2-fluoro-alpha-methyl[1,1'-biphenyl]-4-acetic acid

(S)-(+)-2-Fluoro-α-methyl-4-biphenylacetic acid

[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (S)-

[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (αS)-

d-Flurbiprofen

(S)-2-(2-Fluoro-1,1'-biphenyl-4-yl)propionic acid

(S)-3-Fluoro-α-methyl-4-phenylbenzeneacetic acid

(S)-(+)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofe

2S)-2-(2-Fluoro-4-biphenyl)propanoic acid

Dexflurbiprofen

(S)-(+)-2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID (FLURBIPROFEN)

(S)-2-Flurbiprofen

[1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-methyl-,(aS)-

(S)-2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoic acid

BTS-24332,SFPP,TT-063,Esflurbiprofen

(S)-2-(2-Fluorobiphenyl-4-yl)propanoic acid

CS-1959

Flurbiprofen (S)-Isomer

(S)-Flurbiprofen USP/EP/BP

CS-O-34753Q: What is CS-O-34753 Q: What is the CAS Number of CS-O-34753

(S)-Flurbiprofen，Esflurbiprofen

(+)-Flurbiprofen

Prostaglandin E synthase,PGE synthase,Cyclooxygenase,COX,(S)-Flurbiprofen,(S) Flurbiprofen,Inhibitor,inhibit,(S)Flurbiprofen

C1sH13FO2

(S)-2-(2-Fluoro-4-biphenylyl)propanoic Acid

51543-39-6

C15H13O2F

C6H5C6H3FCHCH3CO2H

Chiral Building Blocks

Asymmetric Synthesis

Carboxylic Acids

Organic Building Blocks