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(-)-Flurbiprofen

(-)-Flurbiprofen structure

CAS No:
51543-40-9
Formula:
C15H13FO2
Chemical Name:
(-)-Flurbiprofen
Synonyms:
[1,1′-Biphenyl]-4-acetic acid,2-fluoro-α-methyl-,(αR)-;[1,1′-Biphenyl]-4-acetic acid,2-fluoro-α-methyl-,(R)-;(αR)-2-Fluoro-α-methyl[1,1′-biphenyl]-4-acetic acid;(-)-Flurbiprofen;l-Flurbiprofen;R-(-)-Flurbiprofen;(-)-(R)-Flurbiprofen;(R)-Flurbiprofen;E 7869;MPC 7869;Tarenflurbil;Flurizan;(R)-(-)-2-(2-Fluorobiphenyl-4-yl)propionic acid;(R)-Flurbiprofen;(2R)-2-(3-Fluoro-4-phenylphenyl)propanoic acid
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

Tarenflurbil ((R)-Flurbiprofen) is the R-enantiomer of the racemate NSAID Flurbiprofen, Tarenflurbil ((R)-Flurbiprofen) inhibits the binding of [3H]9-cis-RA to RXRα LBD with IC50 of 75 μM.

(R)-flurbiprofen is a flurbiprofen. It is an enantiomer of a (S)-flurbiprofen.|Tarenflurbil is an investigational drug that was studied in patients with mild Alzheimer's disease. It is a selective amyloid lowering agent (SALA) that reduces levels of the toxic peptide amyloid beta 42 (Aβ42) in cultured human cells and in animal models. Aβ42 is the primary initiator of neurotoxicity and amyloid plaque development in the brains of Alzheimer's disease patients. In June 2008 development of the drug for Alzheimer's disease was discontinued. Tarenflurbil has also been used in trials studying the treatment of Prostate Cancer.|Tarenflurbil is an orally active synthetic enantiomer of flurbiprofen. Tarenflurbil activates c-Jun N terminal kinase, increases AP-1 binding to DNA, and downregulates cyclin D1 expression, resulting in arrest of tumor cells in the G1 phase of the cell cycle and apoptosis. This agent also affects the expression of nuclear factor kappa B, a rapid response transcription factor that stimulates the immune response to tumor cells. R-flurbiprofen does not inhibit the enzyme cyclo-oxygenase.

(-)-Flurbiprofen Basic Attributes

Molecular Weight：

244.26100

Exact Mass：

244.26

EC Number：

257-264-7

UNII：

501W00OOWA

NSC Number：

685699

DSSTox ID：

DTXSID40199508

NCI Thesaurus Code：

C26666

HScode：

2916399090

Characteristics

PSA：

37.30000

XLogP3：

3.68080

Density：

1.199 g/cm3

Melting Point：

110-113ºC

Boiling Point：

376.2ºC at 760 mmHg

Flash Point：

181.3ºC

Refractive Index：

1.34

Safety Information

Transport codes：

UN 2811

wgk germany：

hazard class code：

R25

safety instructions：

S26-S36/37/39-S45

Marks：

Precautionary statement(s)：

P301 + P310

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 128 companies from 2 notifications to the ECHA C&L Inventory.

Drug Information

Drug Indication：

Investigated for use/treatment in alzheimer's disease and prostate cancer.

Metabolism/Metabolites：

Flurbiprofen has known human metabolites that include (2S,3S,4S,5R)-6-[(2R)-2-(3-fluoro-4-phenylphenyl)propanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

Mechanism of Action：

MPC-7869 is not an inhibitor of cyclooxygenase enzymes (COX-1 and COX-2). The compound modulates the signal transduction and transcription activation pathways associated with nuclear factor kappaB (NFkappaB), a principle transcription factor in the expression of many molecules involved in cell growth, cell death and inflammation. In addition, MPC-7869 has recently been shown to modulate gamma-secretase and selectively lower levels of Abeta42 peptide in vitro and in vivo, and to reduce amyloid pathology in the brain. MPC-7869 has an excellent safety profile and is very potent in animal models of cancer and Alzheimer's disease. In transgenic mouse studies, MPC-7869 reduced brain amyloid levels and prevented memory loss.

MeSH Entry Terms：

flurizan

(-)-Flurbiprofen Use and Manufacturing

(R)-2-Flurbiprofen is the R-isomer of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic.

Computed Properties

Molecular Weight:244.26
XLogP3:4.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:244.08995782
Monoisotopic Mass:244.08995782
Topological Polar Surface Area:37.3
Heavy Atom Count:18
Complexity:286
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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