(R)-2-Flurbiprofen CAS 51543-40-9
(R)-2-Flurbiprofen Basic information
| Product Name: | (R)-2-Flurbiprofen |
| Synonyms: | (R)-2-Fluoro-α-methyl-1,1'-biphenyl-4-acetic acid;(R)-α-Methyl-2-fluoro-1,1'-biphenyl-4-acetic acid;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofe;[1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-Methyl-,(aR)-;Flurizan;MPC 7869;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid 97%;(R)-Flurbiprofen, >=99% |
| CAS: | 51543-40-9 |
| MF: | C15H13FO2 |
| MW: | 244.26 |
| EINECS: | 257-264-7 |
| Product Categories: | API;Pharmaceutical ingredients |
| Mol File: | 51543-40-9.mol |
(R)-2-Flurbiprofen Chemical Properties
| Melting point | 110-113 °C(lit.) |
| Boiling point | 376.2±30.0 °C(Predicted) |
| density | 1.199±0.06 g/cm3(Predicted) |
| storage temp. | Store at RT |
| solubility | DMF: 25 mg/ml; DMSO: 10 mg/ml; Ethanol: 25 mg/ml; PBS (pH 7.2): .9 mg/ml |
| form | Crystalline Powder |
| pka | 4.14±0.10(Predicted) |
| color | 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(C=CC([C@@H](C)C(=O)O)=CC=1F)C1=CC=CC=C1 |&1:4,r| |
Safety Information
| Hazard Codes | T |
| Risk Statements | 25 |
| Safety Statements | 26-36/37/39-45 |
| RIDADR | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| HazardClass | 6.1 |
| HS Code | 29163900 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Oral Repr. 2 Skin Sens. 1B |
| Description | (R)-Flurbiprofen is a COX-inactive enantiomer of the racemic non-selective COX inhibitor flurbiprofen that has diverse biological activities. It inhibits γ-secretase activity in vitro and, in vivo, it reduces formation of amyloid-β peptide 1-42 (Aβ42) and improves axonal transport in young Aβ-plaque free mice but not old mice with existing Aβ plaques in the Tg2576 transgenic model of Alzheimer''s disease. (R)-Flurbiprofen inhibits NF-kB activation and DNA binding as well as AP-1 DNA binding in RAW 264.7 macrophages and reduces paw edema in a rat model of zymosan-induced inflammation via COX-independent inhibition of NF-κB and AP-1 activation when administered at doses of 1, 3, and 9 mg/kg. It also suppresses prostate tumor cell growth in vitro by inducing p75NTR protein expression and reduces tumor growth and metastasis in multiple mouse models of intestinal neoplasia. |
| Uses | (R)-2-Flurbiprofen is the R-isomer of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic. |
| Definition | ChEBI: (R)-flurbiprofen is a flurbiprofen. It is an enantiomer of a (S)-flurbiprofen. |
| Biochem/physiol Actions | gamma secretase inhibitor; amyloid Abeta 42 lowering agent |
| in vivo | Effects of the early and late onset of treatment with Tarenflurbil ((R)-Flurbiprofen) are assessed in C57BL6/J mice that develop a non-remitting form of the disease, and in SJL mice that develop a relapsing-remitting (RR)-EAE. Tarenflurbil ((R)-Flurbiprofen) completely prevents the development of clinical EAE scores in C57BL6/J mice when the treatment is started within 3 days after immunization. This regimen is referred to as preventive treatment. The effect is dose-dependent, and the minimum daily dose for complete prevention is 5 mg/kg/day. Effects of Tarenflurbil ((R)-Flurbiprofen) are comparable to those of Fingolimod (FTY720, 0.5 mg/kg/day), which is used as the positive control. Tarenflurbil ((R)-Flurbiprofen) also significantly reduces clinical EAE scores in C57BL6/J mice when treatment is started shortly before onset of clinical manifestations, referred to as semi-therapeutic (10 mg/kg/day) and reduces clinical scores when the treatment is initiated after full development of the disease on day 13 (5 mg/g/day)[3]. |
| References | [1] THOMAS L. KUKAR. Substrate-targeting γ-secretase modulators[J]. Nature, 2008, 453 7197: 925-929. DOI: 10.1038/nature07055 [2] IRMGARD TEGEDER. Inhibition of NF-KB and AP-1 activation by R- and S-flurbiprofen?,?[J]. FASEB Journal, 2001, 15 1: 2-4. DOI: 10.1096/fasebj.15.1.2 [3] EMILY J QUANN. The aryl propionic acid R-flurbiprofen selectively induces p75NTR-dependent decreased survival of prostate tumor cells.[J]. Cancer research, 2007, 67 7: 3254-3262. DOI: 10.1158/0008-5472.can-06-3657 [4] KAREN D. B. SMITH Robia G P Richard Paylor. R-flurbiprofen improves axonal transport in the Tg2576 mouse model of Alzheimer’s Disease as determined by MEMRI[J]. Magnetic Resonance in Medicine, 2010, 65 5: 1423-1429. DOI: 10.1002/mrm.22733 |
(R)-2-Flurbiprofen Preparation Products And Raw materials
