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About This Item

Empirical Formula (Hill Notation):
C23H27BrFNO2 · xC4H4O4
CAS Number:
Molecular Weight:
448.37 (free base basis)
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
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Quality Level

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

off-white

solubility

water: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

Fc1c(ccc(c1)OCCCCCCN(CC=C)C)C(=O)c2ccc(cc2)Br

InChI

1S/C23H27BrFNO2/c1-3-14-26(2)15-6-4-5-7-16-28-20-12-13-21(22(25)17-20)23(27)18-8-10-19(24)11-9-18/h3,8-13,17H,1,4-7,14-16H2,2H3

InChI key

CMYCCJYVZIMDFU-UHFFFAOYSA-N

General description

An orally bioavailable benzofuranylallylamine compound that acts as a potent, active site targeting, competitive and reversible inhibitor of 2,3-oxidosqualene:lanosterol cyclase activity (OSC; IC50 ~ 6.5 nM against mammalian) and reduces cholesterol synthesis (IC50 ~ 1.5 nM in HepG2 cells) with minimal buildup of both dioxidosqualene and monooxidosqualene. Downregulates 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase mRNA and synthesis, and exerts less adverse effects in animal models than Statins. Shown to preferentially enhance the DNA-binding affinity of mutant p53 and arrest the growth of human breast cancer cells (IC50 ~ 10 µM).

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Thoma, R., et al. 2004. Nature432, 118.
Peffley, D.M., et al. 1998. Biochem. Pharmacol.56, 439.
Morand, O.H., et al. 1997. J. Lipid Res.38, 373.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Regulatory Review (Z)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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