(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

• ChemBase ID: 72804
• Molecular Formular: C25H38O5
• Molecular Mass: 418.56622
• Monoisotopic Mass: 418.27192432
• SMILES: C1[C@H](C=C2[C@H]([C@H]1OC(=O)C(CC)(C)C)[C@H]([C@H](C=C2)C)CC[C@H]1OC(=O)C[C@@H](C1)O)C
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)(C)C
• InChI: 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
• InChIKey: RYMZZMVNJRMUDD-HGQWONQESA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: simvastatin; (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
• Synonyms: Simvastatin; Zocor; Simlup; Simcard; Simvacor; Simvoget; Simvastatin; 2,2-Dimethylbutanoic Acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester; (+)-Simvastatin; Cholestat; Lipex; Novo-Simvastatin; Simvotin; Sinvacor; Statin; Zorced; Colemin; Denan; Liponorm; Lodales; Medipo; Pantok; Sivastin; Synvinolin; Velastatin; Zocord; (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

Database IDs

• CAS Number: 79902-63-9
• MDL Number: MFCD00072007
• PubChem SID: 24724617; 162037725
• PubChem CID: 54454

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.4582014
• LogD (pH = 7.4): 4.4582014
• Log P: 4.4582014
• Molar Refractivity: 117.6834 cm^3
• Polarizability: 46.25644 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO: ≥20 mg/mL; Ether; Ethyl Acetate; Methanol
• Apperance: White Powder; white solid
• Melting Point: 123-125°C; 127-132 °C(lit.)
• Hydrophobicity(logP): 4.481

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS: EK7798000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... HMGCR(3156)rat ... Hmgcr(25675)
• Mechanism of Action: Cholesterol synthesis inhibitor; Decreases LDL cholesterol levels, VLDL cholesterol levels and plasma triglycerides; HMG-CoA reductase inhibitor; Increases HDL cholesterol levels

Product Information

• Purity: ≥97% (HPLC); 95%; 95+%
• Salt Data: Free Base
• Biological Source: Metab. of Aspergillus terreus and Monascus spp.*
• Application(s): Antiarteriosclerotic; Used in the treatment of hypercholesterolaemia, and to reduce risk of death in patients with coronary heart disease and high serum cholesterol levels
• Empirical Formula (Hill Notation): C25H38O5

DETAILS

Selleck Chemicals - S1792

Research Area: Cardiovascular Disease
Biological Activity:
Simvastatin(Zocor) 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. Statins are more effective than other lipid-regulating drugs at lowering LDL-cholesterol concentration but they are less effective than the fibrates in reducing triglyceride concentration. [1]

Sigma Aldrich - S6196

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Simvastatin, a synthetic analog of lovastatin, is a specific inhibitor of HMG-CoA reductase (3-hydroxy-3-methyl-glutaryl-CoA reductase.) HMG-CoA is a major therapeutic target for reduction of low density lipoprotein (LDL) cholesterol. Simvastatin may also have beneficial effects on endothelial function, smooth muscle cell function, hemostasis, vascular wall function, LDL oxidation, and inflammation. Simvastatin can be activated prior to use by treatment with NaOH in EtOH.
Simvastatin is a specific inhibitor of HMG-CoA reductase, the enzyme that catalyzes the conversion of HMG-CoA to mevalonate, an early step in cholesterol biosynthesis. It is used in the treatment of hypercholesterolemia, as it reduces levels of low-density lipoproteins and triglycerides, and raises high-density lipoprotein levels. Simvastatin is a lactone that is readily hydrolyzed in vivo to the corresponding β-hydroxyacid, and can be activated prior to use with NaOH in EtOH treatment. It is a synthetic analog of lovastatin (Cat. No. M2147).

Toronto Research Chemicals - S485000

Simvastatin is a synthetic derivate of a fermentation product of Aspergillus terreus. A competitive inhibitor of HMG-CoA reductase. A synthetic analog of Lovastatin. Antilipemic. Simvastatin, the drug, is sold under the trade name Zocor.

REFERENCES

• http://en.wikipedia.org/wiki/Simvastatin
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• Mol, M.J., et al.: Lancet, 2, 936 (1986)
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• Hopkins, S.J., Drugs of Today (Barcelona), 1989, 25, 645, (rev)
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• Boccuzzi, S.J. et al., Drug Invest., 1993, 5, 135, (clin trials)
• Lancet, 1995, 1274, (clin trial)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1278