Production Method 1

139893-43-9

79902-63-9

Reaction Conditions

1.1 Solvents: Toluene ;  5 h, reflux; 30 min, heated

Reference

Improved synthesis of simvastatin

Li, Wei; et al, Zhongguo Xinyao Zazhi, 2007, 16(3), 225-226

Production Method 2

134970-33-5

79902-63-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide
1.2 Reagents: Ammonium hydroxide ,  Hydrochloric acid
2.1 Reagents: Methanesulfonic acid Solvents: Dichloromethane

Reference

Improvement of synthesis of simvastatin

Fan, Yinglei; et al, Guangdong Huagong, 2015, 42(17),

Production Method 3

134970-30-2

79902-63-9

Reaction Conditions

1.1 Reagents: Butyllithium ,  Pyrrolidine Solvents: Tetrahydrofuran ,  Hexane
2.1 Reagents: Methanesulfonic acid ,  Water Solvents: Methanol
3.1 Reagents: Sodium hydroxide Solvents: Water
3.2 Reagents: Hydrochloric acid Solvents: Water
3.3 Reagents: Ammonia Solvents: Water
3.4 Reagents: Ammonia Solvents: Methanol ,  Water
4.1 Solvents: Toluene

Reference

Synthesis of synvinolin: extremely high conversion alkylation of an ester enolate

Askin, D.; et al, Journal of Organic Chemistry, 1991, 56(16), 4929-32

Production Method 4

139893-43-9

79902-63-9

Reaction Conditions

1.1 Solvents: Toluene ;  0.5 h, 105 °C

Reference

A Cost-Efficient Synthesis of Simvastatin via High-Conversion Methylation of an Alkoxide Ester Enolate

Thaper, Rajesh K.; et al, Organic Process Research & Development, 1999, 3(6), 476-479

Production Method 5

479482-40-1

79902-63-9

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  3 h, rt

Reference

A new synthesis of the antihypercholesterolemic agent simvastatin

Dabak, Kadir; et al, Helvetica Chimica Acta, 2003, 86(3), 673-677

Production Method 6

79902-63-9

Reaction Conditions

1.1 Reagents: Acetic acid ,  Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  24 h, rt

Reference

Synthesis and application of dimethylphenylsilyl chloride to simvastatin asymmetric synthesis

Deng, Fengjie; et al, Zhongguo Yiyao Gongye Zazhi, 2006, 37(4), 225-226

Production Method 7

79902-63-9

Reaction Conditions

1.1 Reagents: Methanesulfonic acid Solvents: Dichloromethane ;  10 - 15 °C; 1 h, 10 - 15 °C
1.2 Reagents: Sodium carbonate ;  0.5 h

Reference

A modified synthetic route of simvastatin

Zhang, Yongtang; et al, Zhongguo Yaowu Huaxue Zazhi, 2010, 20(3), 195-197

Production Method 8

132748-10-8

938063-63-9

79902-63-9

Reaction Conditions

1.1 Solvents: Dimethyl sulfoxide ,  Water ;  25 °C

Reference

Immobilization and Stabilization of an Engineered Acyltransferase for the Continuous Biosynthesis of Simvastatin in Packed-Bed Reactors

Garcia-Marquina, Guillermo; et al, ACS Sustainable Chemistry & Engineering, 2022, 10(30), 9899-9910

Production Method 9

132748-10-8

938063-63-9

79902-63-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ;  8 h, rt
1.2 Catalysts: Acyltransferase Solvents: Dimethyl sulfoxide ;  25 °C

Reference

Biosynthesis of simvastatin

Zhu, Liping; et al, Shengwu Jiagong Guocheng, 2011, 9(5), 11-16

Production Method 10

134970-31-3

79902-63-9

Reaction Conditions

Reference

Method for preparing simvastatin amide disiloxane as simvastatin intermediate

, China, , ,

Simvastatin Raw materials

• Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-8-[(3R,5R)-7-(butylamino)-3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-oxoheptyl]-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl ester
• Simvastatin Impurity 10
• Monacolinic acid J
• Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-8-[2-[(7R,9R)-9-hydroxy-1,4,6-trioxaspiro[4.5]dec-7-yl]ethyl]-3,7-dimethyl-1-naphthalenyl ester
• Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-8-[(3R,5R)-7-(butylamino)-3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-oxoheptyl]-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl ester, (2S)-
• Simvastatin acid ammonium
• Methyl 3-(2,2-Dimethylbutanoylthio)propanoate

Simvastatin Preparation Products

• Simvastatin (79902-63-9)

• 1. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 2. An ion-gating multinanochannel system based on a copper-responsive self-cleaving DNAzyme?
  Yang Chen,Di Zhou,Zheyi Meng,Jin Zhai Chem. Commun., 2016,52, 10020-10023
• 3. An aptamer-based keypad lock system?
  Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang Wang Chem. Commun., 2012,48, 802-804
• 4. An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand?
  Philipp Traber,Stephan Kupfer,Stefanie Gr?fe,Isabelle Baussanne,Martine Demeunynck,Jean-Marie Mouesca,Serge Gambarelli,Vincent Artero,Murielle Chavarot-Kerlidou Chem. Sci., 2018,9, 4152-4159
• 5. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Lactones Delta valerolactones

Simvastatin (CAS No. 79902-63-9): A Comprehensive Guide to Its Properties, Applications, and Market Trends

Simvastatin, with the CAS number 79902-63-9, is a well-known cholesterol-lowering drug belonging to the class of HMG-CoA reductase inhibitors, commonly referred to as statins. This compound has garnered significant attention in the pharmaceutical industry due to its efficacy in managing hypercholesterolemia and reducing the risk of cardiovascular diseases. In this article, we delve into the chemical properties, therapeutic applications, and current market trends of Simvastatin, while addressing some of the most frequently searched questions by users.

The molecular formula of Simvastatin is C₂₅H₃₈O₅, and it is a white to off-white crystalline powder that is practically insoluble in water but soluble in organic solvents like ethanol and acetone. Its mechanism of action involves inhibiting HMG-CoA reductase, a key enzyme in the cholesterol biosynthesis pathway. By blocking this enzyme, Simvastatin effectively lowers LDL cholesterol levels, often referred to as "bad cholesterol," while moderately increasing HDL cholesterol, the "good cholesterol."

One of the most searched topics related to Simvastatin is its side effects and safety profile. Common side effects include muscle pain, digestive issues, and headaches, while rare but serious side effects may involve liver dysfunction or muscle damage (rhabdomyolysis). Patients often inquire about drug interactions, particularly with grapefruit juice, which can increase the drug's concentration in the bloodstream, leading to heightened side effects. Additionally, Simvastatin dosage is a frequently searched term, as the recommended dose varies depending on the patient's condition, ranging from 5 mg to 40 mg per day.

The therapeutic applications of Simvastatin extend beyond cholesterol management. Recent studies have explored its potential in anti-inflammatory and neuroprotective effects, sparking interest in its use for conditions like Alzheimer's disease and multiple sclerosis. This has led to a surge in searches for "Simvastatin and brain health" and "Simvastatin for inflammation," reflecting the growing curiosity about its off-label uses.

From a market perspective, Simvastatin remains a widely prescribed medication, particularly in generic form, making it an affordable option for patients. The global demand for statins continues to rise, driven by increasing awareness of cardiovascular health and the prevalence of high cholesterol worldwide. Searches for "Simvastatin price" and "generic Simvastatin vs brand name" are common, as cost-effectiveness is a significant concern for many users.

In conclusion, Simvastatin (CAS No. 79902-63-9) is a cornerstone in the treatment of hypercholesterolemia and cardiovascular risk reduction. Its well-documented efficacy, combined with ongoing research into additional therapeutic benefits, ensures its relevance in modern medicine. Whether you're a healthcare professional, researcher, or patient, understanding the properties and applications of Simvastatin can provide valuable insights into its role in promoting health and wellness.

• 79902-60-6(Butanoic acid,2-ethyl-2-methyl-,1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenylester, [1S-[1a,3a,7b,8b(2S*,4S*),8ab]]-(9CI))
• 128241-03-2(Butanoic acid,2,2-dimethyl-,1,2,3,7,8,8a-hexahydro-3-(hydroxymethyl)-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenylester, [1S-[1a,3a,7a,8b(2S*,4S*),8ab]]-(9CI))
• 114801-27-3(Butanoic acid,2,2-dimethyl-,1,2,3,7,8,8a-hexahydro-3-(hydroxymethyl)-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenylester, [1S-[1a,3b,7b,8b(2S*,4S*),8ab]]-(9CI))
• 145576-25-6(4'-Acetyl Simvastatin)
• 121624-18-8(6’-Exomethylene Simvastatin)
• 864357-88-0(Simvastatin 4’-Methyl Ether)
• 476305-24-5(Simvastatin Dimer)
• 126313-98-2(3??-HYDROXY SIMVASTATIN)
• 79902-62-8(3-Methylene Simvastatin Impurity)
• 114883-29-3(6’-Hydroxymethyl Simvastatin)