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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
Differential regulation of apolipoprotein B secretion from HepG2 cells by two HMG-CoA reductase inhibitors, atorvastatin and simvastatin.
1999 Jun
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
Rhabdomyolysis and acute renal failure after changing statin-fibrate combinations.
2000
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
Does vitamin E beneficially affect muscle pains during HMG-Co-enzyme-A-reductase inhibitors without CK-elevation?
2000 Mar
Compactin and simvastatin, but not pravastatin, induce bone morphogenetic protein-2 in human osteosarcoma cells.
2000 May 19
Simvastatin modulates cytokine-mediated endothelial cell adhesion molecule induction: involvement of an inhibitory G protein.
2000 Sep 1
A new simvastatin (mevinolin)-resistance marker from Haloarcula hispanica and a new Haloferax volcanii strain cured of plasmid pHV2.
2001 Apr
Clinical and biochemical features, molecular diagnosis and long-term management of a case of cerebrotendinous xanthomatosis.
2001 Apr
Comparative study of HMG-CoA reductase inhibitors on fibrinogen.
2001 Apr
Efficacy and safety of combination simvastatin and colesevelam in patients with primary hypercholesterolemia.
2001 Apr 1
Effect of hydroxymethyl glutaryl coenzyme a reductase inhibitor therapy on high sensitive C-reactive protein levels.
2001 Apr 17
Cost-minimization analysis of simvastatin versus atorvastatin for maintenance therapy in patients with coronary or peripheral vascular disease.
2001 Feb
Clinical relevance of statins: their role in secondary prevention.
2001 Feb
[Statins: intervention studies, facts and perspectives].
2001 Feb
Do HMG-CoA reductase inhibitors affect fibrinogen?
2001 Feb
Anti-inflammatory effects of simvastatin in subjects with hypercholesterolemia.
2001 Feb
Vascular effects of HMG CoA-reductase inhibitors (statins) unrelated to cholesterol lowering: new concepts for cardiovascular disease.
2001 Feb 1
Similar effects of atorvastatin, simvastatin and pravastatin on thrombogenic and inflammatory parameters in patients with hypercholesterolemia.
2001 Jan
How cost-effective is the treatment of dyslipidemia in patients with diabetes but without cardiovascular disease?
2001 Jan
Effective use of statins to prevent coronary heart disease.
2001 Jan 15
Effectiveness of high doses of simvastatin as monotherapy in mixed hyperlipidemia.
2001 Jan 15
[The role of HDL in the prevention of cardiovascular events].
2001 Jan 21
Statins for stroke: the second story?
2001 Jan 23
Simvastatin promotes osteoblast differentiation and mineralization in MC3T3-E1 cells.
2001 Jan 26
Statin therapy--what now?
2001 Mar
Effect of simvastatin on vascular smooth muscle responsiveness: involvement of Ca(2+) homeostasis.
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
Effect of simvastatin in preventing progression of carotid artery stenosis.
2001 Mar 1
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
Pro and con: low-density lipoprotein cholesterol lowering is and will be the key to the future of lipid management.
2001 Mar 8
Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor.
2001 Mar 8
An omega-3 polyunsaturated fatty acid concentrate administered for one year decreased triglycerides in simvastatin treated patients with coronary heart disease and persisting hypertriglyceridaemia.
2001 May
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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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