(S)-Flurbiprofen
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(S)-Flurbiprofen ??
- ???
- 109-110 °C(lit.)
- ?? ?
- 376.2±30.0 °C(Predicted)
- ??
- 1.199±0.06 g/cm3(Predicted)
- ?? ??
- Sealed in dry,Room Temperature
- ???
- insoluble in H2O; ≥10.9 mg/mL in DMSO; ≥69.1 mg/mL in EtOH
- ??? ??
- ??? ??
- ?? ?? (pKa)
- 4.14±0.10(Predicted)
- ??
- White to off-white
- InChI
- InChI=1/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)/t10-/s3
- InChIKey
- SYTBZMRGLBWNTM-JQHDBZEONA-N
- SMILES
- C1(=CC=C([C@H](C)C(=O)O)C=C1F)C1=CC=CC=C1 |&1:4,r|
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- ?? ? ?? ??
- ?? ? ???? ?? (GHS)
| ??? ?? | T | ||
|---|---|---|---|
| ?? ???? ?? | 25 | ||
| ????? | 36/37/39-45 | ||
| ????(UN No.) | UN 2811 6.1/PG 3 | ||
| WGK ?? | 3 |
(S)-Flurbiprofen C??? ??, ??, ??
??
(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.??
(S)-Flurbiprofen is the S-isomer of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic.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.
(S)-Flurbiprofen ?? ?? ? ???
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(S)-Flurbiprofen ?? ??
???( 169)?? ??
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|---|---|---|---|---|---|
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(S)-Flurbiprofen ?? ??:
FLURBI??FEN ??????
Olaparib
Anistreplasa [INN-Spanish]
Acipimox
Aprepitant
Obeticholic Acid
Flibaserin
(R)-2-Flurbiprofen
4-Biphenylacetic acid
3-Fluorophenylacetic acid
(S)-Flurbiprofen
3-Fluoro-4-methylphenylacetic acid
alpha-Methyl-4-biphenylacetic acid
3-FLUORO-4-METHYLPHENETHYL ALCOHOL
(2-FLUORO-4-BIPHENYL)ACETIC ACID
4'-Chloro-5-fluoro-alpha-methyl-3-biphenylacetic acid
5-Fluoro-alpha-methyl-3-biphenylacetic acid