Human Metabolome Database Version 3.5

Showing metabocard for Simvastatin (HMDB05007)

Record Information
Version 3.5
Creation Date 2006-10-16 06:27:59 -0600
Update Date 2013-05-15 15:21:53 -0600
HMDB ID HMDB05007
Secondary Accession Numbers
  • HMDB14779
Metabolite Identification
Common Name Simvastatin
Description Simvastatin 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C25H38O5
Average Molecular Weight 418.5662
Monoisotopic Molecular Weight 418.271924326
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 Name simvastatin
CAS Registry Number 79902-63-9
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 Key RYMZZMVNJRMUDD-HGQWONQESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class N/A
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • a small molecule(Cyc)
Substituents
  • Carboxylic Acid Ester
  • Cyclohexene
  • Dicarboxylic Acid Derivative
  • Lactone
  • Oxane
  • Secondary Alcohol
Direct Parent Fatty Acid Esters
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 135 - 138 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.22e-02 g/L Not Available
LogP 4.68 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.012 g/L ALOGPS
LogP 4.51 ALOGPS
LogP 4.46 ChemAxon
LogS -4.53 ALOGPS
pKa (strongest acidic) 14.91 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 72.83 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 117.68 ChemAxon
Polarizability 47.81 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Muscle
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.044 +/- 0.011 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00641 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023580
KNApSAcK ID Not Available
Chemspider ID 49179 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Simvastatin Link_out
NuGOwiki Link HMDB05007 Link_out
Metagene Link HMDB05007 Link_out
METLIN ID 2443 Link_out
PubChem Compound 54454 Link_out
PDB ID Not Available
ChEBI ID 9150 Link_out
References
Synthesis Reference Willard, 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) Download (PDF)
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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: 3-hydroxy-3-methylglutaryl-coenzyme A reductase
Reactions: Not Available
Gene Name: HMGCR
Uniprot ID: P04035 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Activin receptor type-1
Reactions: Not Available
Gene Name: ACVR1
Uniprot ID: Q04771 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Mitogen-activated protein kinase 3
Reactions: Not Available
Gene Name: MAPK3
Uniprot ID: P27361 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ras-related C3 botulinum toxin substrate 1
Reactions: Not Available
Gene Name: RAC1
Uniprot ID: P63000 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Plasminogen activator inhibitor 1
Reactions: Not Available
Gene Name: SERPINE1
Uniprot ID: P05121 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: C-C motif chemokine 2
Reactions: Not Available
Gene Name: CCL2
Uniprot ID: P13500 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transforming protein RhoA
Reactions: Not Available
Gene Name: RHOA
Uniprot ID: P61586 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Tumor necrosis factor
Reactions: Not Available
Gene Name: TNF
Uniprot ID: P01375 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Interferon gamma
Reactions: Not Available
Gene Name: IFNG
Uniprot ID: P01579 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Integrin beta-2
Reactions: Not Available
Gene Name: ITGB2
Uniprot ID: P05107 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Interleukin-6
Reactions: Not Available
Gene Name: IL6
Uniprot ID: P05231 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Intercellular adhesion molecule 1
Reactions: Not Available
Gene Name: ICAM1
Uniprot ID: P05362 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Matrix metalloproteinase-9
Reactions: Not Available
Gene Name: MMP9
Uniprot ID: P14780 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Vascular endothelial growth factor A
Reactions: Not Available
Gene Name: VEGFA
Uniprot ID: P15692 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisome proliferator-activated receptor alpha
Reactions: Not Available
Gene Name: PPARA
Uniprot ID: Q07869 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bone morphogenetic protein 2
Reactions: Not Available
Gene Name: BMP2
Uniprot ID: P12643 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Interleukin-8
Reactions: Not Available
Gene Name: IL8
Uniprot ID: P10145 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Stromelysin-1
Reactions: Not Available
Gene Name: MMP3
Uniprot ID: P08254 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Angiotensinogen
Reactions: Not Available
Gene Name: AGT
Uniprot ID: P01019 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Collagen alpha-1(XIII) chain
Reactions: Not Available
Gene Name: COL13A1
Uniprot ID: Q5TAT6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Tumor necrosis factor receptor superfamily member 5
Reactions: Not Available
Gene Name: CD40
Uniprot ID: P25942 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lymphotoxin-beta
Reactions: Not Available
Gene Name: LTB
Uniprot ID: Q06643 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA