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Encyclopedia

Simvastatin

Base Information Edit
  • Chemical Name:Simvastatin
  • CAS No.:79902-63-9
  • Deprecated CAS:118607-03-7
  • Molecular Formula:C25H38O5
  • Molecular Weight:418.574
  • Hs Code.:29322090
  • European Community (EC) Number:616-751-8,691-267-8,692-956-6
  • NSC Number:758706,633782
  • UNII:AGG2FN16EV
  • DSSTox Substance ID:DTXSID0023581
  • Nikkaji Number:J152.218C
  • Wikipedia:Simvastatin
  • Wikidata:Q670131
  • NCI Thesaurus Code:C29454
  • RXCUI:36567
  • Pharos Ligand ID:NZ548L771W7J
  • Metabolomics Workbench ID:42962
  • ChEMBL ID:CHEMBL1064
  • Mol file:79902-63-9.mol
Simvastatin

Synonyms:MK 733;MK-733;MK733;Simvastatin;Synvinolin;Zocor

Suppliers and Price of Simvastatin
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Simvastatin
  • 100mg
  • $ 95.00
  • Tocris
  • Simvastatin ≥98%(HPLC)
  • 50
  • $ 196.00
  • TCI Chemical
  • Simvastatin >97.0%(HPLC)
  • 1g
  • $ 485.00
  • TCI Chemical
  • Simvastatin >97.0%(HPLC)
  • 100mg
  • $ 82.00
  • Sigma-Aldrich
  • Simvastatin analytical standard
  • 10mg
  • $ 102.00
  • Sigma-Aldrich
  • Simvastatin Pharmaceutical Secondary Standard; Certified Reference Material
  • 1g
  • $ 78.90
  • Sigma-Aldrich
  • Simvastatin ≥97% (HPLC), solid
  • 5mg
  • $ 43.90
  • Sigma-Aldrich
  • Simvastatin ≥97% (HPLC), solid
  • 25mg
  • $ 163.00
  • Sigma-Aldrich
  • Simvastatin
  • 50mg
  • $ 217.37
  • Sigma-Aldrich
  • Simvastatin British Pharmacopoeia (BP) Reference Standard
  • $ 190.00
Total 294 raw suppliers
Chemical Property of Simvastatin Edit
Chemical Property:
  • Appearance/Colour:White powder 
  • Vapor Pressure:4.12E-15mmHg at 25°C 
  • Melting Point:139 °C 
  • Refractive Index:1.53 
  • Boiling Point:564.9 °C at 760 mmHg 
  • PKA:13.49±0.40(Predicted) 
  • Flash Point:184.8 °C 
  • PSA:72.83000 
  • Density:1.11 g/cm3  
  • LogP:4.58560 
  • Storage Temp.:0-6°C 
  • Solubility.:DMSO: ≥20mg/mL 
  • XLogP3:4.7
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:5
  • Rotatable Bond Count:7
  • Exact Mass:418.27192431
  • Heavy Atom Count:30
  • Complexity:706
Purity/Quality:

Above 99% *data from raw suppliers

Simvastatin *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi 
  • Statements: 36/37/38 
  • Safety Statements: 26-36-24/25 
MSDS Files:

SDS file from LookChem

Useful:
  • Drug Classes:Antilipemic Agents
  • Canonical SMILES:CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
  • Isomeric SMILES:CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C
  • Recent ClinicalTrials:Multi-Center Study of the Effects of Simvastatin on Hepatic Decompensation and Death in Subjects Presenting With High-Risk Compensated Cirrhosis
  • Recent EU Clinical Trials:Randomized phase 2 study of Valproic acid combinEd with Simvastatin and gemcitabine/nab-paclitaxel-based regimens in untreated metastatic Pancreatic Adenocarcinoma patients (The VESPA trial)
  • Recent NIPH Clinical Trials:Study of the Effects of eicosapentaenoic acid on diabetic atherosclerotic lesion
  • Indications 1. Hyperlipidemia: (1) For patients with primary hypercholesterolemia, heterozygous familial hypercholesterolemia or mixed hypercholesterolemia, when diet and other non-drug treatment is not ideal, Simvastatin can be used to reduce the increased total cholesterol, LDL cholesterol, apolipoprotein B and triglycerides. And Simvastatin increases high-density lipoprotein cholesterol, thereby reducing the LDL/HDL and total cholesterol/HDL ratio. (2) For patients with homozygous familial hypercholesterolemia, when diet and non-diet is not ideal, Simvastatin can be used to reduce elevated total cholesterol, LDL cholesterol and apolipoprotein B. 2. Coronary heart disease: Coronary heart disease, Simvastatin can be used to: (1) reduce the risk of death. (2) reduce risk of coronary heart disease death and nonfatal myocardial infarction. (3) reduce risk of stroke and transient ischemic. (4) reduce risk of myocardial revascularization (coronary artery bypass grafting and percutaneous coronary balloon angioplasty). (5) delay the progression of atherosclerosis in the arteries, including the all-new lesions and the occurrence of full clogging. The above information is edited by the lookchem of Liu Yujie.
  • Uses 1. HMG-CoA reductase inhibitors, can reduce the concentration of serum total cholesterol level, inhibit synthesis of cholesterol. For treatment of primary hypercholesterolemia with cholesterol levels greater than 7.8mmol/L which is invalid or not tolerated in other treatments. 2. Has role in reducing cholesterol, low-density lipoprotein cholesterol and very low density lipoprotein cholesterol. A HMGCR inhibitor and anti-proliferative agent. 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. Simvastatin is a synthetic derivative of a fermentation product of Aspergillus terreus. A competitive inhibitor of HMG-CoA reductase. A synthetic analog of Lovastatin. Antilipemic. Simvastatin, the dr ug, is sold under the trade name Zocor. Simvastatin is semi-synthetic, slightly more hydrophobic, analogue of lovastatin. Like lovastatin, simvastatin is a specific inhibitor of HMG-CoA reductase and is used therapeutically to reduce LDL cholesterol. More recently, the statins have become important biochemical probes in cell biology. Their involvement in many events can be correlated to their primary mode of action, however, the mechanism of action of many other effects is less apparent.
  • Description Simvastatin is an once-daily hypolipemic, an analog of lovastatin indicated for the treatment of atherosclerosis. In patients with Type IN or IIB hypercholesterolemia, simvastatin reportedly produces significant reductions in total serum cholesterol, LDL, mglycerides and apolipoprotein-B, while HDL and apolipoprotein-A levels are increased.
  • Therapeutic Function Antihyperlipidemic
  • Clinical Use HMG CoA reductase inhibitor: Primary hypercholesterolaemia
  • Drug interactions Potentially hazardous interactions with other drugs Anti-arrhythmics: increased risk of myopathy with amiodarone - do not exceed 20 mg of simvastatin1 ; increased risk of myopathy with dronedarone. Antibacterials: increased risk of myopathy with clarithromycin, daptomycin, erythromycin and fusidic acid - avoid; possibly increased myopathy with azithromycin; concentration possibly reduced by rifampicin. Anticoagulants: effects of coumarins enhanced. Antiepileptics: concentration reduced by carbamazepine and eslicarbazepine. Antifungals: increased risk of myopathy with fluconazole, itraconazole, posaconazole, ketoconazole, voriconazole and possibly miconazole - avoid; possibly increased risk of myopathy with imidazoles. Antivirals: increased risk of myopathy with atazanavir, indinavir, lopinavir, ritonavir or saquinavir and possibly fosamprenavir, lopinavir or tipranavir - avoid; concentration reduced by efavirenz; avoid with boceprevir, dasabuvir, ombitasvir, paritaprevir and telaprevir; possible increased risk of myopathy with ledipasvir - reduce simvastatin dose; concentration increased by simeprevir - consider reducing simvastatin dose. Calcium-channel blockers: increased risk of myopathy with verapamil, diltiazem and amlodipine - do not exceed 20 mg of simvastatin.1 Ciclosporin: increased risk of myopathy - avoid.1 Cobicistat: avoid with simvastatin. Colchicine: possible increased risk of myopathy. Grapefruit: increased risk of myopathy - avoid. Hormone antagonists: possibly increased risk of myopathy with danazol - avoid.1 Lipid-lowering agents: increased risk of myopathy with fibrates - do not exceed 10 mg of simvastatin except with fenofibrate1 ; gemfibrozil - avoid; concentration increased by lomitapide - do not exceed 40 mg of simvastatin; increased risk of myopathy with nicotinic acid. Ranolazine: concentration increased by ranolazine, maximum dose of simvastatin is 20 mg. Ticagrelor: concentration of simvastatin increased; maximum dose of simvastatin is 40 mg
Technology Process of Simvastatin

There total 49 articles about Simvastatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
In cyclohexane; toluene;
Guidance literature:
In toluene; at 100 ℃; for 6h;
DOI:10.1021/jo00016a023
Guidance literature:
C32H54O5Si; With hydrogenchloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; at 0 - 20 ℃; for 6h;
With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;
Refernces Edit
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