(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编号: 72804
• 分子式: C25H38O5
• 平均质量: 418.56622
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: 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
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 14.914537
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 4.4582014
• LogD (pH = 7.4): 4.4582014
• Log P: 4.4582014
• 摩尔折射率: 117.6834 cm^3
• 极化性: 46.25644 Å^3
• 极化表面积: 72.83 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Dichloromethane; DMSO: ≥20 mg/mL; Ether; Ethyl Acetate; Methanol
• 外观: White Powder; white solid
• 熔点: 123-125°C; 127-132 °C(lit.)
• 疏水性(logP): 4.481

安全信息

• 保存条件: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS编号: EK7798000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... HMGCR(3156)rat ... Hmgcr(25675)
• 生物活性机理: Cholesterol synthesis inhibitor; Decreases LDL cholesterol levels, VLDL cholesterol levels and plasma triglycerides; HMG-CoA reductase inhibitor; Increases HDL cholesterol levels

产品相关信息

• 纯度: ≥97% (HPLC); 95%; 95+%
• 成盐信息: Free Base
• 生物来源: Metab. of Aspergillus terreus and Monascus spp.*
• 应用领域: 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

详细说明

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.

参考文献

• http://en.wikipedia.org/wiki/Simvastatin
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• Mol, M.J., et al.: Lancet, 2, 936 (1986)
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• Am. J. Med., Suppl. 4A, 1989, 87, (rev)
• Hopkins, S.J., Drugs of Today (Barcelona), 1989, 25, 645, (rev)
• Pietro, D.A. et al., Cardiovasc. Drug Rev., 1990, 8, 220, (rev)
• Todd, P. et al., Drugs, 1990, 40, 583, (rev)
• Uchiyama, N. et al., Chem. Pharm. Bull., 1991, 39, 236
• Grundy, S.M., Drug Treatment of Hyperlipidemia, (Ed. Rifkind, B.M.), M. Dekker, 1991, 139, (rev)
• Carlucci, G. et al., J. Pharm. Biomed. Anal., 1992, 10, 693, (hplc)
• Ellison, D.K. et al., Anal. Profiles Drug Subst., 1993, 22, 359, (rev)
• Mauro, V.F., Clin. Pharmacokinet., 1993, 24, 195, (rev)
• 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