EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:9150 - simvastatin

Default Structure
ChEBI IDCHEBI:9150
ChEBI Namesimvastatin
Stars
DefinitionA member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.
Secondary ChEBI IDCHEBI:45577
Last Modified28 October 2021
DownloadsMolfile
FormulaC25H38O5
Net Charge0
Average Mass418.574
Monoisotopic Mass418.27192
SMILES[H][C@@]12C(=C[C@H](C)C[C@@H]1OC(=O)C(C)(C)CC)C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1
InChIInChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKeyRYMZZMVNJRMUDD-HGQWONQESA-N
Wikipedia
Roles Classification
Biological Roles:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
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.
anti-HBV agent  An antiviral agent that destroys or inhibits the replication of the hepatitis B virus.
ferroptosis inducer  Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
antiviral agent  A substance that destroys or inhibits replication of viruses.
anti-obesity agent  Any substance which is used to reduce or control weight.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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:
antirheumatic drug  A drug used to treat rheumatoid arthritis.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
anti-anaemic agent  A compound which increases either the number of red cells or the amount of haemoglobin in the blood.
hypoglycemic agent  A drug which lowers the blood glucose level.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
anticonvulsant  A drug used to prevent seizures or reduce their severity.
anti-arrhythmia drug  A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antiatherosclerotic agent  A cardiovascular drug that prevents atherosclerosis (a disease in which the inside of an artery narrows due to the build up of plaque). Compare with antiatherogenic agent.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
ChEBI Ontology
Outgoing Relation(s)
simvastatin (CHEBI:9150) has functional parent lovastatin (CHEBI:40303)
simvastatin (CHEBI:9150) has role analgesic (CHEBI:35480)
simvastatin (CHEBI:9150) has role anti-anaemic agent (CHEBI:75835)
simvastatin (CHEBI:9150) has role anti-arrhythmia drug (CHEBI:38070)
simvastatin (CHEBI:9150) has role anti-asthmatic agent (CHEBI:65023)
simvastatin (CHEBI:9150) has role anti-HBV agent (CHEBI:64951)
simvastatin (CHEBI:9150) has role anti-HIV agent (CHEBI:64946)
simvastatin (CHEBI:9150) has role anti-inflammatory agent (CHEBI:67079)
simvastatin (CHEBI:9150) has role anti-obesity agent (CHEBI:74518)
simvastatin (CHEBI:9150) has role antiatherosclerotic agent (CHEBI:145947)
simvastatin (CHEBI:9150) has role antibacterial agent (CHEBI:33282)
simvastatin (CHEBI:9150) has role anticonvulsant (CHEBI:35623)
simvastatin (CHEBI:9150) has role antidepressant (CHEBI:35469)
simvastatin (CHEBI:9150) has role antihypertensive agent (CHEBI:35674)
simvastatin (CHEBI:9150) has role antimicrobial agent (CHEBI:33281)
simvastatin (CHEBI:9150) has role antineoplastic agent (CHEBI:35610)
simvastatin (CHEBI:9150) has role antiparkinson drug (CHEBI:48407)
simvastatin (CHEBI:9150) has role antipsychotic agent (CHEBI:35476)
simvastatin (CHEBI:9150) has role antirheumatic drug (CHEBI:35842)
simvastatin (CHEBI:9150) has role antiviral agent (CHEBI:22587)
simvastatin (CHEBI:9150) has role cardiovascular drug (CHEBI:35554)
simvastatin (CHEBI:9150) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
simvastatin (CHEBI:9150) has role EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255)
simvastatin (CHEBI:9150) has role ferroptosis inducer (CHEBI:173085)
simvastatin (CHEBI:9150) has role geroprotector (CHEBI:176497)
simvastatin (CHEBI:9150) has role hepatoprotective agent (CHEBI:62868)
simvastatin (CHEBI:9150) has role hypoglycemic agent (CHEBI:35526)
simvastatin (CHEBI:9150) has role immunosuppressive agent (CHEBI:35705)
simvastatin (CHEBI:9150) has role ophthalmology drug (CHEBI:66981)
simvastatin (CHEBI:9150) has role prodrug (CHEBI:50266)
simvastatin (CHEBI:9150) is a fatty acid ester (CHEBI:35748)
simvastatin (CHEBI:9150) is a hexahydronaphthalenes (CHEBI:142348)
simvastatin (CHEBI:9150) is a statin (semi-synthetic) (CHEBI:87633)
simvastatin (CHEBI:9150) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
INN  Source
simvastatinDrugBank
Synonyms  Source
2,2-dimethylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-oneChemIDplus
C10AA01ChEMBL
MK-0733ChEMBL
MK-733KEGG DRUG
NSC-758706ChEMBL
SimvastatinKEGG DRUG
Brand Names  Source
FlolipidChEMBL
LacersaChEMBL
RanzolontChEMBL
SimvadorChEMBL
Simvastatin component of juvisyncChEMBL
Simvastatin component of polycapChEMBL
Manual XrefsDatabases
2445DrugCentral
D00434KEGG DRUG
DB00641DrugBank
EP33538Patent
HMDB0005007HMDB
LSM-2492LINCS
SimvastatinWikipedia
US4444784Patent
Registry NumbersSources
Beilstein:4768037Beilstein
CAS:79902-63-9KEGG DRUG
CAS:79902-63-9ChemIDplus
Citations