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:CB5380541, eMolecules:511977, ZINC000118912393
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Testosterone is the primary male sex hormone and androgen in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testicles and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. It is associated with increased aggression, sex drive, dominance, courtship display, and a wide range of behavioral characteristics. In addition, testosterone in both sexes is involved in health and well-being, where it has a significant effect on overall mood, cognition, social and sexual behavior, metabolism and energy output, the cardiovascular system, and in the prevention of osteoporosis. Insufficient levels of testosterone in men may lead to abnormalities including frailty, accumulation of adipose fat tissue within the body, anxiety and depression, sexual performance issues, and bone loss. Excessive levels of testosterone in men may be associated with hyperandrogenism, higher risk of heart failure, increased mortality in men with prostate cancer, and male pattern baldness. Testosterone is a steroid hormone from the androstane class containing a ketone and a hydroxyl group at positions three and seventeen respectively. It is biosynthesized in several steps from cholesterol and is converted in the liver to inactive metabolites. It exerts its action through binding to and activation of the androgen receptor. In humans and most other vertebrates, testosterone is secreted primarily by the testicles of males and, to a lesser extent, the ovaries of females. On average, in adult males, levels of testosterone are about seven to eight times as great as in adult females. As the metabolism of testosterone in males is more pronounced, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone. In addition to its role as a natural hormone, testosterone is used as a medication to treat hypogonadism and breast cancer. Since testosterone levels decrease as men age, testosterone is sometimes used in older men to counteract this deficiency. It is also used illicitly to enhance physique and performance, for instance in athletes. The World Anti-Doping Agency lists it as S1 Anabolic agent substance "prohibited at all times".
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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 Types Sources
11273020 PubMed citation Europe PMC
12147804 PubMed citation Europe PMC
18410471 PubMed citation Europe PMC
18413661 PubMed citation Europe PMC
18452779 PubMed citation Europe PMC
18936176 PubMed citation Europe PMC
23212095 PubMed citation Europe PMC
23846727 PubMed citation Europe PMC
Last Modified
16 August 2018