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143201-11-0

143201-11-0 Structure

143201-11-0 Structure
IdentificationMore
[Name]

Cerivastatin sodium
[CAS]

143201-11-0
[Synonyms]

BAYCOL
CERIVASTATIN
Rivastatin, Baycol, Lipobay
6-Heptenoic acid, 7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-, monosodium salt, (3R,5S,6E)-
6-Heptenoic acid, 7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-, monosodium salt, [S-[R*,S*-(E)]]-
BAY-w 6228
Cerivastatin sodium
Sodium 7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-dipropan-2-yl-pyrid in-3-yl]-3,5-dihydroxy-hept-6-enoate
[Molecular Formula]

C26H34FNO5
[MDL Number]

MFCD00865716
[Molecular Weight]

459.55
[MOL File]

143201-11-0.mol
Chemical PropertiesBack Directory
[Appearance]

Solid
[Melting point ]

197-199°C
[alpha ]

D20 +24.1° (c = 1 in ethanol)
[storage temp. ]

Hygroscopic, Store under Inert atmosphere -20°C Freezer
[solubility ]

H2O: ≥5mg/mL
[form ]

powder
[color ]

white to tan
[Optical Rotation]

[α]/D +18 to +26° in ethanol
[Water Solubility ]

H2O: ≥5mg/mL
[Usage]

A competitive inhibitor of HMG-CoA reductase.
[Stability:]

Hygroscopic
[CAS DataBase Reference]

143201-11-0(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[WGK Germany ]

3
Hazard InformationBack Directory
[Hazard]

A poison by ingestion.
[Description]

Lipobay was launched in Denmark, Germany and the UK for treatment of primary hypercholesteremia types Ⅱa and Ⅱb. It is available through a nine step synthesis beginning with the Hantsch reaction of ethyl 3-amino-4-methylpent-2-enoate and 4-(ethoxycarbonyl)-5-(4-fluorophenyl)-2-methylpent-4-en-3-one. Lipobay acts as an HMG-CoA reductase inhibitor showing a high liver selectivity (50 fold). In vitro Lipobay had a higher affinity (110x) for the enzyme than does Lovastatin, Simvastatin and pravastatin which resulted in a lower ED50, in vivo compared to Lovastatin. Three metabolites generated by the CYP3A4 enzyme system were equal to the parent in activity. Lipobay was as effective as Gemfibrozil in type lib hypercholesteremia and had no age or gender effects. It decreased plasma levels of VLDL and LDL cholesterol by a mechanism similar to other HMG-CoA reductase inhibitors. The (-)- antipode is completely inactive indicating a high stereospecificity by the enzyme. It is therapeutically useful at ultra-low doses which may minimize any drug-drug interactions.
[Chemical Properties]

Solid
[Originator]

Bayer (Germany)
[Uses]

Cerivastatin sodium salt hydrate has been used as a supplement in cell culture.
[Uses]

A competitive inhibitor of HMG-CoA reductase.
[Uses]

Cerivastatin is a competitive inhibitor of HMG-CoA reductase.
[Definition]

ChEBI: The sodium salt of cerivastatin. Formerly used to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.
[Brand name]

Baycol (Bayer).
[General Description]

Cerivastatin sodium salt hydrate belongs to the statin class of lipid lowering agents. It helps in decreasing MAP kinase activation, blocking AP-1 (activator protein-1) and NF-kB (nuclear factor-kB ) binding activity, inhibiting inflammatory responses and ameliorated renal damage. It also lowers cholesterol. It is metabolized by cytochrome P450 (CYP)3A4 and (CYP)2C8. Cerivastatin sodium salt hydrate is linked to rhabdomyolysis.
[Biochem/physiol Actions]

Cerivastatin sodium is an HMG-CoA reductase inhibitor. HMG-CoA is a key enzyme in the production of cholesterol.
Spectrum DetailBack Directory
[Spectrum Detail]

Cerivastatin sodium(143201-11-0)1HNMR
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