(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
- Molecular Weight:
- 244.26
- MOL File:
- 51543-39-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/11/19 23:02:33
| 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 |
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 | |||||||||
| Risk Statements | 25 | |||||||||
| Safety Statements | 36/37/39-45 | |||||||||
| RIDADR | UN 2811 6.1/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| NFPA 704 |
|
(S)-Flurbiprofen Chemical Properties,Uses,Production
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.
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 Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GMFC LABS PVT LTD | +91-9133370278 +91-9133370278 | Hyderabad, India | 44 | 58 | Inquiry |
| Integrin Life Sciences. Pvt. Ltd. | +91-4040265469 +91-9849990870 | Hyderabad, India | 90 | 58 | Inquiry |
| SynZeal Research Pvt Ltd | +1 226-802-2078 | Gujarat, India | 6514 | 58 | Inquiry |
| Chemicea Pharmaceuticals Pvt Ltd | +91-9881765045/+91-8796656135 | Pune, India | 825 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6754 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6739 | 58 | Inquiry |
| Sun Pharmaceutical Industries Ltd. | 91-22-43244324 | Maharashtra, India | 99 | 58 | Inquiry |
| SUN PHARMACEUTICAL INDUSTRIES LTD | (+91 22) 4324 4324 | New Delhi, India | 175 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6100 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6257 | 58 | Inquiry |
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