ChemicalBook > CAS DataBase List > (S)-Flurbiprofen

(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
More
Less

(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)
More
Less

Safety

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

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..…

More
Less

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
More
Less

(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 F1α (6-keto-PGF1α; ) 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

More
Less

(S)-Flurbiprofen Suppliers

Canada 1 China 102 Germany 1 India 10 Japan 1 Switzerland 2 Ukraine 1 United Kingdom 4 United States 13 Global 135
Chengdu Senior Pharma Technology Co.Ltd.
Tel
+86-0838-2319818 +86-15982001943
Email
seniorpharma@163.com
Country
China
ProdList
408
Advantage
55
Pushan Industry (Shaanxi) Co., Ltd.
Tel
029-81310890 13571859809
Email
info@pushanshiye.com
Country
China
ProdList
10005
Advantage
58
Viwit Pharmaceutical Co., Ltd.
Tel
0632-2980981 15063270987
Fax
0632-2989678
Email
service.china3@viwit.com
Country
China
ProdList
116
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94838
Advantage
76
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
17989
Advantage
64
Tianjin heowns Biochemical Technology Co., Ltd.
Tel
400 638 7771
Email
sales@heowns.com
Country
China
ProdList
14443
Advantage
57
Maya High Purity Chemicals
Tel
+86 (573) 82222445 (0)18006601000 452520369
Fax
+86 (573) 82222643
Email
sales@maya-r.com
Country
China
ProdList
11714
Advantage
57
Wuhan ariel chemical Co., LTD.
Tel
18986259541 18986259541
Fax
027-87840182
Email
sales@3stc.com
Country
China
ProdList
3941
Advantage
58
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9901
Advantage
58
ShangHai Caerulum Pharma Discovery Co., Ltd.
Tel
18149758185
Email
sales-cpd@caerulumpharma.com
Country
China
ProdList
3421
Advantage
58
ChemStrong Scientific Co.,Ltd
Tel
0755-0755-66853366 13670046396
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
17994
Advantage
56
AdooQ Bioscience CHINA
Tel
025-58849295 18951903616;
Fax
025-68650336
Email
info@adooq.cn
Country
China
ProdList
2989
Advantage
60
Credit Asia Chemical Co., Ltd.
Tel
+86 (21) 61124340
Fax
+86 (21) 6129-4103
Country
China
ProdList
9767
Advantage
58
ATK CHEMICAL COMPANY LIMITED
Tel
3429815786 13301662590
Fax
+86-21-51619052
Email
sales@atkchemical.com
Country
China
ProdList
10006
Advantage
55
parabiochem
Tel
025-83453382-8005
Fax
025-83453382
Email
sale@parabiochem.com
Country
China
ProdList
9604
Advantage
55
Chengdu Dianchun Technology Co., Ltd
Tel
400-1166-196 18502815961
Fax
QQ：800101999
Email
cdhxsj@163.com
Country
China
ProdList
14623
Advantage
60
ShangHai Biochempartner Co.,Ltd
Tel
17754423994 17754423994
Fax
QQ:2853530913
Email
2853530910@QQ.com
Country
China
ProdList
8011
Advantage
62
Lynnchem
Tel
86-(0)29-85992781 17792393971
Email
info@lynnchem.com
Country
China
ProdList
4587
Advantage
58
Wellman Pharmaceutical Group Limited
Tel
027-027-83778875 15807197853
Fax
027-83991220
Email
15807197853@163.com
Country
China
ProdList
3978
Advantage
58
Capot Chemical Co.,Ltd.
Tel
571-85586718 +8613336195806
Fax
+86-571-85864795
Email
sales@capotchem.com
Country
China
ProdList
29797
Advantage
60
Aikon International Limited
Tel
025-58851090 13611564524
Fax
(6)02557626880
Email
lwan@aikonchem.com
Country
China
ProdList
15952
Advantage
58
Hunan Eurasian Pharmaceutical Co. Ltd.
Tel
0592-5789919 13328776692
Email
2851802016@qq.com
Country
China
ProdList
66
Advantage
58
Shenzhen Polymeri Biochemical Technology Co., Ltd.
Tel
+86-400-002-6226 13028896684
Email
sales@rrkchem.com
Country
China
ProdList
55896
Advantage
58
TOSUN PHARM
Tel
020-61855200 13326451905
Email
2881290884@qq.com
Country
China
ProdList
7497
Advantage
58
Hefei TNJ Chemical Industry Co.,Ltd.
Tel
0551-65418671
Fax
0551-65418697
Email
sales@tnjchem.com
Country
China
ProdList
34572
Advantage
58
sgtlifesciences pvt ltd
Tel
+8617013299288
Email
dj@sgtlifesciences.com
Country
China
ProdList
12382
Advantage
58
Dayang Chem (Hangzhou) Co.,Ltd.
Tel
571-88938639 +8617705817739
Fax
+86-571-88938652，+86-571- 88492614
Email
info@dycnchem.com
Country
CHINA
ProdList
52867
Advantage
58
Dideu Industries Group Limited
Tel
+86-29-89586680 +86-15129568250
Email
1026@dideu.com
Country
China
ProdList
28608
Advantage
58
Hubei Jusheng Technology Co.,Ltd.
Tel
18871490254
Fax
027-59599243
Email
linda@hubeijusheng.com
Country
CHINA
ProdList
28180
Advantage
58
Tianjin shijia biomedical technology co., LTD
Tel
15022261580;411316762
Email
tjshj1212@163.com
Country
China
ProdList
2310
Advantage
58
Beijing xinyanhui pharmaceutical research and development co., LTD
Tel
13969155946
Email
1461866103@qq.com
Country
China
ProdList
16111
Advantage
58
Changzhou Yinghao Technology Development Co., Ltd
Tel
15151934985
Email
sales@yingsapharm.com
Country
China
ProdList
4282
Advantage
58
ChemeGen(Shanghai) Biotechnology Co.,Ltd.
Tel
18818260767
Fax
QQ 3610331285
Email
sales@chemegen.com
Country
China
ProdList
11289
Advantage
58
Shenzhen ruikai de biotechnology co., ltd.
Tel
0755-61348847 17820674378
Fax
0755-21016893
Email
2682116078@qq.com
Country
China
ProdList
7844
Advantage
58
Shanghai Xinlitai Pharmaceutical Co. , Ltd.
Tel
18616665298
Email
wenjie.li@bocimed.com
Country
China
ProdList
226
Advantage
58
Nanjing wangzhixing Pharmaceutical Technology Co., Ltd
Tel
15850510341
Fax
025-85722793
Email
shiqingran@wzxchem.com
Country
China
ProdList
3539
Advantage
58
Shanghai Kaiwei Chemical Technology Co., Ltd.
Tel
021-58461859 15821823057
Email
service@aiviche.com
Country
China
ProdList
49323
Advantage
58
career henan chemical co
Tel
+86-0371-86658258 15093356674;
Fax
0086-371-86658258
Email
factory@coreychem.com
Country
China
ProdList
29826
Advantage
58
Shaanxi Dideu Medichem Co. Ltd
Tel
+86-29-87569265 +86-18612256290
Fax
029-88380327
Email
1056@dideu.com
Country
China
ProdList
3335
Advantage
58
Shenzhen Jianyi Biotechnology Co., Ltd
Tel
0755-84826604
Email
3001783715@qq.com
Country
CHINA
ProdList
2898
Advantage
58
Taizhou Nanfeng Pharmaceutical Research Institute
Tel
12345678910
Fax
nanfengdrug@163
Email
nanfengdrug@163.com
Country
China
ProdList
15323
Advantage
58
Wuhan Dingxintong Pharmaceutical Co. , Ltd.
Tel
027-027-52344656 15871722230
Fax
2796190295
Email
15871722230@163.com
Country
China
ProdList
3000
Advantage
58
MedBioPharmaceutical Technology Inc
Tel
021-69568360 18916172912
Email
order@med-bio.cn
Country
China
ProdList
8141
Advantage
58
Energy Chemical
Tel
021-58432009 400-005-6266
Fax
021-58436166
Email
marketing@energy-chemical.com
Country
China
ProdList
44941
Advantage
58
Shandong Territorial sea Biological Technology Co., LTD
Tel
15092083467
Email
18660263263@163.com
Country
China
ProdList
2474
Advantage
58
cjbscvictory
Tel
13348960310 13348960310
Email
3003867561@qq.com
Country
China
ProdList
9946
Advantage
58
Hangzhou Verychem Science And Technology Co.Ltd
Tel
+86-86-57188162785 13606544505
Fax
+86-571-81906939
Email
lucy@verychem.com
Country
China
ProdList
1007
Advantage
58
Hubei Qifei Pharmaceutical Chemical Co., Ltd
Tel
027-027-59322506 18071128681
Fax
027-59322506
Email
1438082200@qq.com
Country
China
ProdList
9995
Advantage
58
Hubei xingongli Chemical Co., Ltd
Tel
027-59503710 15172325309
Fax
027-59503710
Email
1400858877@qq.com
Country
China
ProdList
9965
Advantage
58
Huaian Jiamu Biotechnology Co., Ltd.
Tel
0517-83187139 18205232085
Email
cai@jiamu-bio.com
Country
China
ProdList
980
Advantage
58
More
Less

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 Medichem Co. Ltd
Product
(S)-Flurbiprofen 51543-39-6
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-04-29
Shaanxi Dideu Medichem Co. Ltd
Product
(S)-Flurbiprofen 51543-39-6
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07

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-[1,1'-biphenyl]-4-yl)propanoic acid
  • 51543-39-6
  • C15H13O2F
  • C6H5C6H3FCHCH3CO2H
  • Chiral Building Blocks
  • Asymmetric Synthesis
  • Carboxylic Acids
  • Organic Building Blocks