Esflurbiprofen

Base Information

• Chemical Name: Esflurbiprofen
• CAS No.: 51543-39-6
• Molecular Formula: C₁₅H₁₃FO₂
• Molecular Weight: 244.265
• European Community (EC) Number: 257-263-1
• NSC Number: 685700
• UNII: J5ZZK9P7MX
• DSSTox Substance ID: DTXSID201316678
• Wikidata: Q27104495
• NCI Thesaurus Code: C80544
• Pharos Ligand ID: THHA67PSNQPY
• Metabolomics Workbench ID: 52315
• ChEMBL ID: CHEMBL435298
• Mol file: 51543-39-6.mol

Synonyms:51543-39-6;esflurbiprofen;(S)-flurbiprofen;(S)-(+)-2-Fluoro-alpha-methyl-4-biphenylacetic acid;(S)-2-(2-Fluoro-[1,1'-biphenyl]-4-yl)propanoic acid;Esflurbiprofene;Esflurbiprofeno;Esflurbiprofenum;S-Flurbiprofen;(S)-2-(2-fluorobiphenyl-4-yl)propanoic acid;Flurbiprofen, (s)-;Esflurbiprofene [French];Esflurbiprofenum [Latin];Esflurbiprofeno [Spanish];UNII-J5ZZK9P7MX;BTS 24332;BTS-24332;TT-063;J5ZZK9P7MX;(2S)-2-(3-fluoro-4-phenylphenyl)propanoic acid;(S)-2-Fluoro-alpha-methyl-4-biphenylacetic acid;Esflurbiprofen [INN:BAN];loqoa;CHEMBL435298;CHEBI:42446;EINECS 257-263-1;Esflurbiprofen (JAN);ESFLURBIPROFEN [JAN];(S)-2-Fluoro-alpha-methyl(1,1'-biphenyl)-4-acetic acid;SFPP;SMR000471846;(S)-(+)-Flurbiprofen;(2S)-2-(2-fluorobiphenyl-4-yl)propanoic acid;(S)-2-fluoro-alpha-methyl[1,1'-biphenyl]-4-acetic acid;Flurwood;Urbifen;(+)-Flurbiprofen;FLP;flurbiprofen-(S)-(+);D0G2IC;Esflurbiprofen [BAN:INN];ESFLURBIPROFEN [INN];MLS001066337;MLS001333207;MLS001333208;SCHEMBL505817;GTPL9420;ESFLURBIPROFEN [WHO-DD];(S)-2-(2-Fluoro-[1,1'-biphenyl]-4-yl)propanoicacid;DTXSID201316678;HMS2232E18;HMS3649P05;HMS3884I06;BCP24046;BDBM50172479;MFCD00866152;NSC685700;s1679;AKOS016844131;CCG-266907;NSC-685700;AS-78108;HY-15123;NCI60_030810;NCI60_030811;CS-0003779;SW202926-2;A21120;D10254;SR-01000946685;(S)-(+)-2-Fluoro-?-methyl-4-biphenylacetic acid;SR-01000946685-1;Q27104495;(S)-(+)-2-Fluoro-.alpha.-methyl-4-biphenylacetic acid;(2S)-2-(2-fluoro-[1,1'-biphenyl-4-yl])propanoic acid;(S)-2-FLUORO-.ALPHA.-METHYL-4-BIPHENYLACETIC ACID;(1,1'-Biphenyl)-4-acetic acid, 2-fluoro-alpha-methyl-, (S)-

Chemical Property of Esflurbiprofen

Chemical Property:

• Appearance/Colour: White to yellowish crystalline powder
• Vapor Pressure: 2.5E-06mmHg at 25°C
• Melting Point: 109-110 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 376.2 °C at 760 mmHg
• PKA: 4.14±0.10(Predicted)
• Flash Point: 181.3 °C
• PSA: 37.30000
• Density: 1.199 g/cm³
• LogP: 3.68080
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: insoluble in H2O; ≥10.9 mg/mL in DMSO; ≥69.1 mg/mL in EtOH
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 244.08995782
• Heavy Atom Count: 18
• Complexity: 286

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Flurbiprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O
• Isomeric SMILES: C[C@@H](C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O
• Recent ClinicalTrials: Safety and Efficacy of SFPP in Knee Osteoarthritis
• Recent EU Clinical Trials: Randomized, controlled, double-blind, multi-center trial to evaluate the
• Recent NIPH Clinical Trials: Multicentered Randomized study for knee osteoarthritis
• 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. (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.

Technology Process of Esflurbiprofen

There total 179 articles about Esflurbiprofen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-(2-fluoro-biphenyl-4-yl)-acrylic acid → (R)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9)

Guidance literature:

With C₅₄H₇₂IrNP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; caesium carbonate; In methanol; at 45 ℃; for 0.25h; under 4500.45 Torr; Pressure; Glovebox;

Reference yield: 90.0%

formic acid (64-18-6) + 3-fluoro-4-phenyl-1-ethynylbenzene → (R)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9)

Guidance literature:

With (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; bis(acetylacetonate)nickel(II); acetic anhydride; triethylamine; In 1,4-dioxane; at 70 ℃; for 24h; Inert atmosphere; Sealed tube;

Reference yield: 88.0%

(S)-(+)-1,1-diphenyl-3-(3-fluoro-4-phenylphenyl)-1-butene → (R)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9)

Guidance literature:

With sodium periodate; ruthenium trichloride; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1021/ol702261t

upstream raw materials:

(S)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose

methyl 2-(2-fluoro-4-biphenylyl)propionate

fluorobiprofen

methanol

Downstream raw materials:

fluorobiprofen

(R)-flurbiprofen

(S)-(+)-flurbiprofen

(R)-2-(2-fluoro-biphenyl-4-yl)-N-(3-{3-[4-(3-{3-[2-(2-fluoro-biphenyl-4-yl)-(R)-propionylamino]-propylamino}-propylamino)-3,6-dioxo-cyclohexa-1,4-dienylamino]-propylamino}-propyl)-propionamide

Refernces

• 1、 Chen, Hua,Dai, Yuhao,Liu, Yu,Luo, Kaihong,Zhang, Yi. "An efficient method for the synthesis of (S)-flurbiprofen by 1,2-rearrangement of the aryl group". . . Retrieved 2022/03/15.
• 2、 -. "Preparation method of flurbiprofen". Paragraph 0066; 0078-0079. . Retrieved 2021/05/12.