Esflurbiprofen (BTS-24332; TT 063; BTS24332; TT063; SFPP; BTS 24332; TT-063; Trade name: Loqoa), the S-enantiomrer or S-isomer of Flurbiprofen, is a potent cyclooxygenase (COX) inhibitor and a nonsteroidal anti-inflammatory drugs (NSAIDs) with antipyretic and analgesic activity.
Physicochemical Properties
| Molecular Formula | C15H13FO2 |
| Molecular Weight | 244.2654 |
| Exact Mass | 244.089 |
| CAS # | 51543-39-6 |
| PubChem CID | 72099 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 376.2±30.0 °C at 760 mmHg |
| Melting Point | 109-110ºC(lit.) |
| Flash Point | 181.3±24.6 °C |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.568 |
| LogP | 4.11 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 18 |
| Complexity | 286 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | C[C@@H](C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O |
| InChi Key | SYTBZMRGLBWNTM-JTQLQIEISA-N |
| InChi Code | InChI=1S/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-/m0/s1 |
| Chemical Name | (2S)-2-(3-fluoro-4-phenylphenyl)propanoic acid |
| Synonyms | BTS-24332; TT 063; BTS24332; TT063; SFPP; BTS 24332; TT-063; Trade name: Loqoa |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | (S)-Flurbiprofen (10–7 M) completely transcribes the dye's basal and induced PGE2 release [2]. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites (s)-flurbiprofen has known human metabolites that include 4-hydroxy-S-flurbiprofen. |
| References |
[1]. Stereoselective Inhibition of Inducible Cyclooxygenase by Chiral Nonsteroidal Antiinflammatory Drugs. J Clin Pharmacol. 1996 Jun;36(6):505-12. [2]. Inflammatory Mediators Do Not Stimulate CGRP Release if Prostaglandin Synthesis Is Blocked by S(+)-flurbiprofen in Isolated Rat Skin. Inflamm Res. 2003 Dec;52(12):519-23. |
| Additional Infomation |
(S)-flurbiprofen is a flurbiprofen. It is an enantiomer of a (R)-flurbiprofen. Esflurbiprofen is under investigation in clinical trial NCT03434197 (Safety and Efficacy of SFPP in Knee Osteoarthritis). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~409.40 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0938 mL | 20.4692 mL | 40.9383 mL | |
| 5 mM | 0.8188 mL | 4.0938 mL | 8.1877 mL | |
| 10 mM | 0.4094 mL | 2.0469 mL | 4.0938 mL |