U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H38O5
Molecular Weight 418.5662
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SIMVASTATIN

SMILES

CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H]12

InChI

InChIKey=RYMZZMVNJRMUDD-HGQWONQESA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C25H38O5
Molecular Weight 418.5662
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Simvastatin is a HMG-CoA Reductase Inhibitor that is FDA approved for the treatment of hypercholesterolemia and for the reduction in the risk of cardiac heart disease mortality and cardiovascular events. It reduces levels of "bad" cholesterol (low-density lipoprotein, or LDL) and triglycerides in the blood, while increasing levels of "good" cholesterol (high-density lipoprotein, or HDL). Common adverse reactions include abdominal pain, constipation, nausea, headache, upper respiratory infection. Cases of myopathy/rhabdomyolysis have been observed with simvastatin co-administered with lipid-modifying doses ( ≥ 1 g/day niacin) of niacin-containing products. The risk of myopathy, including rhabdomyolysis, is increased by concomitant administration of amiodarone, dronedarone, ranolazine, or calcium channel blockers such as verapamil, diltiazem, or amlodipine.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Rhabdomyolysis and cholestatic hepatitis under treatment with simvastatin and chlorzoxazone].
1999 Apr 3
Atorvastatin and simvastatin have distinct effects on hydroxy methylglutaryl-CoA reductase activity and mRNA abundance in the guinea pig.
1999 Dec
Direct inhibitory effects of simvastatin on matrix accumulation in cultured murine mesangial cells.
1999 Jul
Effect of simvastatin on proliferative nephritis and cell-cycle protein expression.
1999 Jul
Differential regulation of apolipoprotein B secretion from HepG2 cells by two HMG-CoA reductase inhibitors, atorvastatin and simvastatin.
1999 Jun
Effect of simvastatin, a 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor, on alpha-fetoprotein gene expression through interaction with the ras-mediated pathway.
1999 May
Effect of simvastatin treatment on the electronegative low-density lipoprotein present in patients with heterozygous familial hypercholesterolemia.
1999 Sep 15
Comparative effects of simvastatin and cholestyramine on plasma lipoproteins and CETP in humans.
1999 Summer
Calf and forearm blood flow in hypercholesterolemic patients.
2000 Apr
Rhabdomyolysis and acute renal failure in a cardiac transplant recipient due to multiple drug interactions.
2000 Dec
Simvastatin upregulates coronary vascular endothelial nitric oxide production in conscious dogs.
2000 Dec
Differences in the effects of HMG-CoA reductase inhibitors on proliferation and viability of smooth muscle cells in culture.
2000 Jun
Inhibitors of sterol biosynthesis and amphotericin B reduce the viability of pneumocystis carinii f. sp. carinii.
2000 Jun
Does vitamin E beneficially affect muscle pains during HMG-Co-enzyme-A-reductase inhibitors without CK-elevation?
2000 Mar
Simvastatin attenuates vascular hypercoagulability in cardiac transplant recipients.
2000 May 15
Compactin and simvastatin, but not pravastatin, induce bone morphogenetic protein-2 in human osteosarcoma cells.
2000 May 19
A paradoxical severe decrease in serum HDL-cholesterol after treatment with a fibrate.
2000 Oct
Long-term effects of cholesterol lowering and angiotensin-converting enzyme inhibition on coronary atherosclerosis: The Simvastatin/Enalapril Coronary Atherosclerosis Trial (SCAT).
2000 Oct 10
Simvastatin modulates cytokine-mediated endothelial cell adhesion molecule induction: involvement of an inhibitory G protein.
2000 Sep 1
Involvement of Rho GTPases in the transcriptional inhibition of preproendothelin-1 gene expression by simvastatin in vascular endothelial cells.
2000 Sep 29
Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice.
2001 Apr
Rhabdomyolysis due to simvastatin in a transplant patient: Are some statins safer than others?
2001 Apr
Effect of hydroxymethyl glutaryl coenzyme a reductase inhibitor therapy on high sensitive C-reactive protein levels.
2001 Apr 17
Clinical relevance of statins: their role in secondary prevention.
2001 Feb
Anti-inflammatory effects of simvastatin in subjects with hypercholesterolemia.
2001 Feb
Fats, lipids and blood coagulation.
2001 Feb
Preoperative lipid control with simvastatin reduces the risk for graft failure already 1 year after myocardial revascularization.
2001 Feb
Effect of simvastatin on micropulmonary red cell mass in patients with hyperlipoproteinemia.
2001 Feb 1
Fibrinogen response with simvastatin versus atorvastatin in familial hypercholesterolemia.
2001 Feb 1
Vascular effects of HMG CoA-reductase inhibitors (statins) unrelated to cholesterol lowering: new concepts for cardiovascular disease.
2001 Feb 1
Safety and efficacy of simvastatin for hyperlipidemia in renal transplant recipients: a double-blind, randomized, placebo-controlled study.
2001 Feb-Mar
Similar effects of atorvastatin, simvastatin and pravastatin on thrombogenic and inflammatory parameters in patients with hypercholesterolemia.
2001 Jan
[Antioxidative effects of fluvastatin, and its major metabolites [II]].
2001 Jan
Rhabdomyolysis secondary to a drug interaction between simvastatin and clarithromycin.
2001 Jan
Simvastatin has anti-inflammatory and antiatherosclerotic activities independent of plasma cholesterol lowering.
2001 Jan
Effective use of statins to prevent coronary heart disease.
2001 Jan 15
Use of the statins in patients after acute myocardial infarction: does evidence change practice?
2001 Jan 22
High-dose simvastin (80 mg/day) decreases plasma concentrations of total homocyst(e)ine in patients with hypercholesteromia.
2001 Mar
Effect of simvastatin on vascular smooth muscle responsiveness: involvement of Ca(2+) homeostasis.
2001 Mar
Making the most of cholesterol-lowering margarines.
2001 Mar
Cholesterol metabolism in primary biliary cirrhosis during simvastatin and UDCA administration.
2001 Mar
HMG-CoA reductase inhibitors and P-glycoprotein modulation.
2001 Mar
Simvastatin treatment on postprandial hypertriglyceridemia in type 2 diabetes mellitus patients with combined hyperlipidemia.
2001 Mar
Simvastatin improves arterial compliance in the lower limb but not in the aorta.
2001 Mar
Effects of simvastatin treatment on sICAM-1 and sE-selectin levels in hypercholesterolemic subjects.
2001 Mar
A comparison of the effects of 3-hydroxy-3-methylglutaryl-coenzyme a (HMG-CoA) reductase inhibitors on the CYP3A4-dependent oxidation of mexazolam in vitro.
2001 Mar
Coronary artery reactivity after treatment with simvastatin.
2001 Mar
Comparison of efficacy and safety of atorvastatin (10mg) with simvastatin (10mg) at six weeks. ASSET Investigators.
2001 Mar 1
Magnetic resonance detects changes in phosphocholine associated with Ras activation and inhibition in NIH 3T3 cells.
2001 Mar 2
Cost effectiveness of HMG-CoA reductase inhibition in Canada.
2001 Spring
Patents

Sample Use Guides

In Vivo Use Guide
Dose range is 5 to 40 mg/day. Recommended usual starting dose is 10 or 20 mg once a day in the evening (for patients at high risk of Coronary heart defect is 40 mg/day). Due to the increased risk of myopathy, including rhabdomyolysis, use of the 80-mg dose of Simvastatin should be restricted to patients who have been taking simvastatin 80 mg chronically (e.g., for 12 months or more) without evidence of muscle toxicity.
Route of Administration: Oral
In Vitro Use Guide
Simvastatin (30 μM) significantly (P <0.01) inhibited the proliferative effect of H2O2 (0.5 mM) and its stimulatory actions on ERK1/2 phosphorylation, NF-κB activation and IL-8 production.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:42:28 UTC 2019
Edited
by admin
on Mon Oct 21 20:42:28 UTC 2019
Record UNII
AGG2FN16EV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SIMVASTATIN
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
SIMVASTATIN [EP]
Common Name English
SIMVASTATIN [MI]
Common Name English
SIMVASTATIN [JAN]
Common Name English
MK-0733
Code English
ZOCOR
Brand Name English
SIMVASTATIN [INN]
Common Name English
SIMVASTATIN COMPONENT OF SIMCOR
Common Name English
C10AA01
Code English
SIMCOR COMPONENT SIMVASTATIN
Common Name English
SIMVASTATIN [MART.]
Common Name English
SYNVINOLIN
Common Name English
SIMVASTATIN [ORANGE BOOK]
Common Name English
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-ONE
Common Name English
VYTORIN COMPONENT SIMVASTATIN
Common Name English
SIMVASTATIN [VANDF]
Common Name English
MK-733
Code English
SIMVASTATIN [HSDB]
Common Name English
SIMVASTATIN [USAN]
Common Name English
SIMVASTATIN [WHO-DD]
Common Name English
POLYCAP COMPONENT SIMVASTATIN
Brand Name English
SIMVASTATIN [USP]
Common Name English
BUTANOIC ACID, 2,2-DIMETHYL-, 1,2,3,7,8,8A-HEXAHYDRO-3,7-DIMETHYL-8-(2-(TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-1-NAPHTHALENYL ESTER, (1S-(1.ALPHA.,3.ALPHA.,7.BETA.,8.BETA.(2S*,4S*),8A.BETA.))-
Common Name English
SIMVASTATIN [USP-RS]
Common Name English
SIMVASTATIN COMPONENT OF VYTORIN
Common Name English
Classification Tree Code System Code
WHO-ATC C10BX04
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-ATC C10BA04
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-VATC QC10BA04
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
NCI_THESAURUS C1655
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-ATC A10BH51
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
NDF-RT N0000175589
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
LIVERTOX 888
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-VATC QC10BA02
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-VATC QC10AA01
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-VATC QA10BH51
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-ATC C10BA02
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
NDF-RT N0000000121
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-ATC C10AA01
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-VATC QC10BX01
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-ATC C10BX01
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 12.6
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
WHO-VATC QC10BX04
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
Code System Code Type Description
LactMed
79902-63-9
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
EPA CompTox
79902-63-9
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
HSDB
79902-63-9
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
ChEMBL
CHEMBL1064
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
NCI_THESAURUS
C29454
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
INN
6147
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
MERCK INDEX
M9947
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY Merck Index
MESH
D019821
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
CAS
79902-63-9
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
WIKIPEDIA
SIMVASTATIN
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
DRUG BANK
DB00641
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
EVMPD
SUB10529MIG
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
PUBCHEM
54454
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
RXCUI
36567
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY RxNorm
IUPHAR
2955
Created by admin on Mon Oct 21 20:42:28 UTC 2019 , Edited by admin on Mon Oct 21 20:42:28 UTC 2019
PRIMARY
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sum of impurities E and F: not more than twice the area of the principal peak in the chromatogram obtained with reference solution (b) (1.0 per cent)
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EP
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SIMVASTATIN ACID
PHARMACOKINETIC
Tmax PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC