Record Information
Version3.6
Creation Date2006-10-16 12:27:59 UTC
Update Date2013-05-15 21:21:53 UTC
HMDB IDHMDB05007
Secondary Accession Numbers
  • HMDB14779
Metabolite Identification
Common NameSimvastatin
DescriptionSimvastatin is a hypolipidemic drug belonging to the class of pharmaceuticals called 'statins'. It is used to control hypercholesterolemia (elevated cholesterol levels) and to prevent cardiovascular disease. Simvastatin is a synthetic derivate of a fermentation product of Aspergillus terreus; Simvastatin is a powerful lipid-lowering drug that can decrease low density lipoprotein (LDL) levels by up to 50 percent. It is used in doses of 5 mg up to 80 mg. Higher doses (160 mg) have been found to be too toxic, while giving only minimal benefit in terms of lipid lowering. There is no real effect on HDL and triglyceride levels. Simvastatin (INN) is a hypolipidemic drug belonging to the class of pharmaceuticals called 'statins'. It is used to control hypercholesterolemia (elevated cholesterol levels) and to prevent cardiovascular disease. Simvastatin is a synthetic derivate of a fermentation product of Aspergillus terreus; The drug is the form of an inactive lactone that is hydrolized after ingestion to produce the active agent. It is a white, nonhygroscopic, crystalline powder that is practically insoluble in water, and freely soluble in chloroform, methanol and ethanol; Ezetimibe/simvastatin is a combination product to lower lipids and marketed as Vytorin.
Structure
Thumb
Synonyms
  1. (+)-Simvastatin
  2. Cholestat
  3. Denan
  4. Eucor
  5. Kolestevan
  6. Lipex
  7. Lipinorm
  8. Liponorm
  9. Lipovas
  10. Lodales
  11. Modutrol
  12. Nor-Vastina
  13. Pepstatin
  14. Rechol
  15. Simcor
  16. Simovil
  17. Simvastatin
  18. Simvastatin lactone
  19. Simvotin
  20. Sinvacor
  21. Sinvascor
  22. Sivastin
  23. Statin
  24. Synvinolin
  25. Valemia
  26. Velostatin
  27. Zocor
  28. Zocord
Chemical FormulaC25H38O5
Average Molecular Weight418.5662
Monoisotopic Molecular Weight418.271924326
IUPAC Name(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
Traditional IUPAC Namesimvastatin
CAS Registry Number79902-63-9
SMILES
[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC
InChI Identifier
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
InChI KeyRYMZZMVNJRMUDD-HGQWONQESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassN/A
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • a small molecule(Cyc)
Substituents
  • Carboxylic Acid Ester
  • Cyclohexene
  • Dicarboxylic Acid Derivative
  • Lactone
  • Oxane
  • Secondary Alcohol
Direct ParentFatty Acid Esters
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Endogenous
  • Food
Biofunction
  • Anticholesteremic Agents
  • Antilipemic Agents
  • Cell signalling
  • Fuel and energy storage
  • Fuel or energy source
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • Membrane integrity/stability
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point135 - 138 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.22e-02 g/LNot Available
LogP4.68HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility0.012 g/LALOGPS
logP4.51ALOGPS
logP4.46ChemAxon
logS-4.5ALOGPS
pKa (strongest acidic)14.91ChemAxon
pKa (strongest basic)-2.8ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area72.83ChemAxon
rotatable bond count7ChemAxon
refractivity117.68ChemAxon
polarizability47.81ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.044 +/- 0.011 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00641
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023580
KNApSAcK IDNot Available
Chemspider ID49179
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSimvastatin
NuGOwiki LinkHMDB05007
Metagene LinkHMDB05007
METLIN ID2443
PubChem Compound54454
PDB IDNot Available
ChEBI ID9150
References
Synthesis ReferenceWillard, Alvin K.; Smith, Robert L.; Hoffman, William F. 6(R)-[2-(8-acyloxy-2-methyl-6-methyl (or hydrogen)-polyhydro-1-naphthyl)ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones, the hydroxy acid forms of these pyranones, salts and esters thereof, and a pharmaceutical antihypercholesterolemic composition containing them. Eur. Pat. Appl. (1981), 54 pp. CODEN: EPXXDW EP 33538 19810812 CAN 95:219968 AN 1981:619968
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mahboobi SK, Shohat EZ, Jellinek SP, Rose M: Systemic infections can decrease the threshold of statin-induced muscle injury. South Med J. 2006 Apr;99(4):403-4. Pubmed: 16634254
  2. Antons KA, Williams CD, Baker SK, Phillips PS: Clinical perspectives of statin-induced rhabdomyolysis. Am J Med. 2006 May;119(5):400-9. Pubmed: 16651050
  3. Tsivgoulis G, Spengos K, Karandreas N, Panas M, Kladi A, Manta P: Presymptomatic neuromuscular disorders disclosed following statin treatment. Arch Intern Med. 2006 Jul 24;166(14):1519-24. Pubmed: 16864763
  4. Finsterer J, Zuntner G: Rhabdomyolysis from Simvastatin triggered by infection and muscle exertion. South Med J. 2005 Aug;98(8):827-9. Pubmed: 16144183
  5. Soininen K, Niemi M, Kilkki E, Strandberg T, Kivisto KT: Muscle symptoms associated with statins: a series of twenty patients. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):51-4. Pubmed: 16433891
  6. Davidson MH, Maccubbin D, Stepanavage M, Strony J, Musliner T: Striated muscle safety of ezetimibe/simvastatin (Vytorin). Am J Cardiol. 2006 Jan 15;97(2):223-8. Epub 2005 Nov 21. Pubmed: 16442367
  7. Hellinger FJ, Encinosa WE: Inappropriate drug combinations among privately insured patients with HIV disease. Med Care. 2005 Sep;43(9 Suppl):III53-62. Pubmed: 16116309
  8. Wolozin B, Wang SW, Li NC, Lee A, Lee TA, Kazis LE: Simvastatin is associated with a reduced incidence of dementia and Parkinson's disease. BMC Med. 2007 Jul 19;5:20. Pubmed: 17640385

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
ACVR1
Uniprot ID:
Q04771
Gene Name:
MAPK3
Uniprot ID:
P27361
Gene Name:
CYP2C8
Uniprot ID:
P10632
Gene Name:
SERPINE1
Uniprot ID:
P05121
Gene Name:
CCL2
Uniprot ID:
P13500
Gene Name:
RHOA
Uniprot ID:
P61586
Gene Name:
TNF
Uniprot ID:
P01375
Gene Name:
IFNG
Uniprot ID:
P01579
Gene Name:
ITGB2
Uniprot ID:
P05107
Gene Name:
IL6
Uniprot ID:
P05231
Gene Name:
ICAM1
Uniprot ID:
P05362
Gene Name:
MMP9
Uniprot ID:
P14780
Gene Name:
VEGFA
Uniprot ID:
P15692
Gene Name:
BMP2
Uniprot ID:
P12643
Gene Name:
IL8
Uniprot ID:
P10145
Gene Name:
MMP3
Uniprot ID:
P08254
Gene Name:
AGT
Uniprot ID:
P01019
Gene Name:
COL13A1
Uniprot ID:
Q5TAT6
Gene Name:
LTB
Uniprot ID:
Q06643