| Identification | Back Directory | [Name]
(R)-2-Flurbiprofen | [CAS]
51543-40-9 | [Synonyms]
E-7869
(R)-FL
Flurizan
MPC 7869
Furbiprofen
Tarenflurbil
Flurbiprofene
l-Flurbiprofen
2-Flurbiprofen
Flurbiprofen CRS
(R)-FLURBIPROFEN
(R)-2-FLUBIPROFEN
(R)-2-Flurbiprofen
(R)-2-Flurbiprofenr
(R)-(-)-FLURBIPROFEN
(R)-Flurbiprofen, >=99%
Flurbiprofen (R)-Isomer
(R)-Flurbiprofen
(E7869
E7869,Tarenflurbil,MPC7869
(R)-2-Flurbiprofen USP/EP/BP
(R)-2-Flurbiprofen, Tarenflurbil
(2R)-2-(3-fluoro-4-phenyl-phenyl)propanoic aci
(R)-(?)-2-Fluoro-α-methyl-4-biphenylacetic acid
(R)-(-)-2-Fluoro-α-methyl-4-biphenylacetic acid
(R)-2-Fluoro-α-methyl-1,1'-biphenyl-4-acetic acid
(R)-α-Methyl-2-fluoro-1,1'-biphenyl-4-acetic acid
(R)-2-(2-Fluoro-1,1'-biphenyl-4-yl)propionic acid
(R)-(-)-2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID
[1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-Methyl-,(aR)-
(R)-2-fluoro-alpha-methyl[1,1'-biphenyl]-4-acetic acid
(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid 97%
[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (R)-
[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (αR)-
(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofe
(R)-(-)-2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID (FLURBIPROFEN) | [EINECS(EC#)]
257-264-7 | [Molecular Formula]
C15H13FO2 | [MDL Number]
MFCD00869714 | [MOL File]
51543-40-9.mol | [Molecular Weight]
244.26 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
(R)-Flurbiprofen is a COX-inactive enantiomer of the racemic non-selective COX inhibitor flurbiprofen (Item No. 70250) that has diverse biological activities.1,2,3,4 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.1,4 (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.2 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.3,2 | [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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