ChemicalBook Product Catalog API Antipyretic analgesics Nonsteroidal Anti-Inflammatory Drugs (NSAIDS) (R)-2-Flurbiprofen

(R)-2-Flurbiprofen

Product Name(R)-2-Flurbiprofen
CAS51543-40-9
MFC15H13FO2
MW244.26
EINECS257-264-7
MOL File51543-40-9.mol

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
pka	4.14±0.10(Predicted)
form	Crystalline Powder
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

MSDS

Provider	Language
SigmaAldrich	English

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 p75^NTR 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 Supplier

(R)-2-Flurbiprofen manufacturers

Related Product Information

Send Inquriy