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CHEBI:38561 - fluvastatin

ChEBI IDCHEBI:38561
ChEBI Namefluvastatin
Stars
DefinitionA 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.
Last Modified16 August 2018
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC24H26FNO4
Net Charge0
Average Mass411.473
Monoisotopic Mass411.18459
SMILESCC(C)n1c(/C=C/[C@H](O)C[C@H](O)CC(=O)O)c(-c2ccc(F)cc2)c2ccccc21
InChIInChI=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
InChIKeyFJLGEFLZQAZZCD-JUFISIKESA-N
Wikipedia
Roles Classification
Biological Roles:
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.
Applications:
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
ChEBI Ontology
Outgoing Relation(s)
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  Source
fluvastatinWHO MedNet
fluvastatinaWHO MedNet
fluvastatineWHO MedNet
fluvastatinumWHO MedNet
Synonyms  Source
rac-(3R,5S,6E)-7-(3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl)-3,5-dihydroxy-6-heptenoic acidChEBI
rac-(3R,5S)-fluvastatinChEBI
erythro-(E)-3,5-dihydroxy-7-[3'-(4''-fluorophenyl)-1'-(1''-methylethyl)indol-2'-yl]hept-6-enoic acidChEBI
(±)-fluvastatinChEBI
(6E)-erythro7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acidChEBI
Brand Name  Source
CranocChemIDplus
Manual XrefsDatabases
D07983KEGG DRUG
FluvastatinWikipedia
C07014KEGG COMPOUND
DB01095DrugBank
WO8402131Patent
US4739073Patent
Registry NumbersSources
Beilstein:9168031Beilstein
CAS:93957-54-1ChemIDplus
CAS:93957-54-1KEGG COMPOUND
Citations