EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:3559 - cerivastatin sodium

ChEBI IDCHEBI:3559
ChEBI Namecerivastatin sodium
Stars
DefinitionThe 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 Formerly used to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.
Last Modified24 August 2015
DownloadsMolfile
FormulaC26H33FNO5.Na
Net Charge0
Average Mass481.540
Monoisotopic Mass481.22405
SMILESCOCc1c(C(C)C)nc(C(C)C)c(/C=C/[C@@H](O)C[C@@H](O)CC(=O)[O-])c1-c1ccc(F)cc1.[Na+]
InChIInChI=1S/C26H34FNO5.Na/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4;/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32);/q;+1/p-1/b11-10+;/t19-,20-;/m1./s1
InChIKeyGPUADMRJQVPIAS-QCVDVZFFSA-M
Roles Classification
Biological Role:
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor  Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme.
Application:
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
ChEBI Ontology
Outgoing Relation(s)
cerivastatin sodium (CHEBI:3559) has part cerivastatin(1−) (CHEBI:406059)
cerivastatin sodium (CHEBI:3559) is a organic sodium salt (CHEBI:38700)
cerivastatin sodium (CHEBI:3559) is a statin (synthetic) (CHEBI:87635)
IUPAC Name 
sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoate
Synonym  Source
(+)-sodium (3R,5S,6E)-7-(4-(p-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoateChemIDplus
Manual XrefsDatabases
D00889KEGG DRUG
US5177080Patent
DB00439DrugBank
Registry NumbersSources
Beilstein:8466341Beilstein
CAS:143201-11-0ChemIDplus