CHEBI:3558 - cerivastatin

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ChEBI Name cerivastatin
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 Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.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
Monoisotopic Mass 459.24210
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
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 (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 for the NADPH-dependent enzyme and EC for an NADH-dependent enzyme.
(via statin )
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
View more via ChEBI Ontology
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)
(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
Manual Xrefs Databases
577 DrugCentral
Cerivastatin Wikipedia
DB00439 DrugBank
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Registry Numbers Types Sources
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
22 February 2017