CHEBI:38561 - fluvastatin

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ChEBI Name fluvastatin
ChEBI ID CHEBI:38561
Definition A racemate comprising equimolar amounts of (3R,5S)- and (3S,5R)-fluvastatin. An HMG-CoA reductase inhibitor, it is used (often as the corresponding sodium salt) to reduce triglycerides and LDL-cholesterol, and increase HDL-chloesterol, in the treatment of hyperlipidaemia.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB03386396, eMolecules:10141252, ZINC000001530639
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Formula C24H26FNO4
Net Charge 0
Average Mass 411.467
Monoisotopic Mass 411.18459
InChI InChI=1S/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/m0/s1
InChIKey FJLGEFLZQAZZCD-JUFISIKESA-N
SMILES C1(=CC=C(C=C1)C=2C=3C(N(C2/C=C/[C@@H](C[C@@H](CC(O)=O)O)O)C(C)C)=CC=CC3)F
Roles Classification
Biological Role(s): EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of anthrax lethal factor endopeptidase (EC 3.4.24.83).
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 fluvastatin (CHEBI:38561) has part (3R,5S)-fluvastatin (CHEBI:38565)
fluvastatin (CHEBI:38561) has part (3S,5R)-fluvastatin (CHEBI:5136)
fluvastatin (CHEBI:38561) has role anticholesteremic drug (CHEBI:35821)
fluvastatin (CHEBI:38561) has role EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255)
fluvastatin (CHEBI:38561) is a racemate (CHEBI:60911)
fluvastatin (CHEBI:38561) is a statin (synthetic) (CHEBI:87635)
IUPAC Name
rac-(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
INNs Sources
fluvastatin WHO MedNet
fluvastatina WHO MedNet
fluvastatine WHO MedNet
fluvastatinum WHO MedNet
Synonyms Sources
(±)-fluvastatin ChEBI
(6E)-erythro7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid ChEBI
erythro-(E)-3,5-dihydroxy-7-[3'-(4''-fluorophenyl)-1'-(1''-methylethyl)indol-2'-yl]hept-6-enoic acid ChEBI
rac-(3R,5S)-fluvastatin ChEBI
rac-(3R,5S,6E)-7-(3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl)-3,5-dihydroxy-6-heptenoic acid ChEBI
Brand Name Source
Cranoc ChemIDplus
Manual Xrefs Databases
C07014 KEGG COMPOUND
D07983 KEGG DRUG
DB01095 DrugBank
Fluvastatin Wikipedia
US4739073 Patent
WO8402131 Patent
View more database links
Registry Numbers Types Sources
9168031 Beilstein Registry Number Beilstein
93957-54-1 CAS Registry Number KEGG COMPOUND
93957-54-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
16 August 2018