(R)-2-Flurbiprofen
(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
MSDS
- Language:English Provider:SigmaAldrich
(R)-2-Flurbiprofen Usage And Synthesis
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
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