CHEBI:3558 - cerivastatin

Main ChEBI Ontology Automatic Xrefs
ChEBI Name cerivastatin
ChEBI ID CHEBI:3558
Definition (3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:503465
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Formula C26H34FNO5
Net Charge 0
Average Mass 459.55030
InChI InChI=1S/C26H34FNO5/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)/b11-10+/t19-,20-/m1/s1
InChIKey SEERZIQQUAZTOL-ANMDKAQQSA-N
SMILES COCc1c(nc(C(C)C)c(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)c1-c1ccc(F)cc1)C(C)C
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
(via statin )
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
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ChEBI Ontology
Outgoing cerivastatin (CHEBI:3558) is a dihydroxy monocarboxylic acid (CHEBI:35972)
cerivastatin (CHEBI:3558) is a pyridines (CHEBI:26421)
cerivastatin (CHEBI:3558) is a statin (synthetic) (CHEBI:87635)
cerivastatin (CHEBI:3558) is conjugate acid of cerivastatin(1−) (CHEBI:406059)
Incoming cerivastatin(1−) (CHEBI:406059) is conjugate base of cerivastatin (CHEBI:3558)
IUPAC Name
(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
INN Source
cerivastatin ChemIDplus
Synonyms Sources
(3R,5S,6E)-7-(4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoic acid ChemIDplus
(3R,5S,6E)-7-(4-(p-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoic acid ChemIDplus
(3R,5S,E)-7-(4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoic acid ChEMBL
Cerivastatin KEGG COMPOUND
cerivastatin acid ChEBI
Database Links Databases
C07966 KEGG COMPOUND
Cerivastatin Wikipedia
D07661 KEGG DRUG
DB00439 DrugBank
View more database links
Registry Numbers Types Sources
145599-86-6 CAS Registry Number KEGG COMPOUND
145599-86-6 CAS Registry Number ChemIDplus
8366578 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17560788 PubMed citation ChEMBL
18155906 PubMed citation ChEMBL
Last Modified
24 August 2015