101314-97-0

Basic information

• Product Name: SIMVASTATIN, SODIUM SALT
• Synonyms: SIMVASTATIN HYDROXY ACID SODIUM SALT;SIMVASTATIN, SODIUM SALT;IMp. A (EP) as SodiuM Salt: (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-DiMethylbutanoyl)oxy]-2,6-diMethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic Acid SodiuM Salt (Tenivastatin SodiuM Salt;SiMvastatin IMp. A (EP) as SodiuM Salt;Simvastatin Impurity as Sodium Salt;Simvastati;Simvastatin EP Impurity A Sodium Salt;FYSMQCWXGBXWLB-VMCZNHHFSA-M
• CAS NO: 101314-97-0
• Molecular Formula: C₂₅H₃₉O₆*Na
• Molecular Weight: 458.56
• Mol File: 101314-97-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: SIMVASTATIN, SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: SIMVASTATIN, SODIUM SALT(101314-97-0)
• EPA Substance Registry System: SIMVASTATIN, SODIUM SALT(101314-97-0)

Safety Data

• Hazardous Substances Data: 101314-97-0(Hazardous Substances Data)

Usage

Description

Simvastatin is a competitive inhibitor of HMG-CoA reductase (Ki = 0.12 nM). Simvastatin reduces plasma cholesterol levels in rats and dogs when administered at doses of 1.2 and 8 mg/kg, respectively. Simvastatin suppresses TNF-induced NF-κB activation (IC50 = ~13 μM) and potentiates apoptosis in human myeloid leukemia cells. It also inhibits glutathione peroxidase 4 (GPX4) activity, increases malondialdehyde (MDA) levels, and induces ferroptosis in MDA-MB-231 and MCF-7 breast cancer cells. Formulations containing simvastatin have been used in the treatment of dyslipidemias.

Uses

Simvastatin Hydroxy Acid Sodium Salt is a metabolite of Simvastatin (S485000), 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 drug, is sold under the trade name Zocor.

in vitro

previous study found that simvastatin could inhibit the incorporation of 14c-acetate to 14c-sterol with an ic50 value of 15 nm in cultured hep g2 cells. in addition, simvastatin was found to be a potent inhibitor of cholesterol synthesis in cultured liver cells, whereas pravastatin inhibited cholesterol synthesis in liver cells only after these cells had been digested by collagenase [1].

in vivo

animal study showd that rats orally dosed with simvastatin had lower plasma cholesterol levels after 4 days of treatment. at the level of 0.02% of the diet, simvastatin lowered plasma cholesterol levels in rats by 64%. moreove, in dogs, simvastatin at a daily oral dosage of 8 mg/kg lower levels of plasma cholesterol. at this dosage, simvastatin was slightly more potent than lovastatin and the levels of plasma cholesterol in these dogs returned to pretreatment levels after stopping the treatment [1].

references

[1] chao, y. ,chen, j.s.,hunt, v.m., et al. lowering of plasma cholesterol levels in animals by lovastatin and simvastatin. european journal of clinical pharmacology 40, s11-s14 (1991).[2] s martande s, kumari m, pradeep ar, pal singh s, kumar suke d. ncomparative evaluation of efficacy of subgingivally delivered 1.2% atorvastatin and 1.2% simvastatin in the treatment of intrabony defects in chronic periodontitis: a randomized controlled trial. j dent res dent clin dent prospects. 2017 winter;11(1):18-25.

Upstream product

• 75330-75-5 lovastatin 
• 938063-63-9 methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate 
• 132748-10-8 (3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid 
• 5856-77-9 2,2-dimethylbutanoyl chloride 
• 123049-81-0 simvastatin 

Downstream Products

• 139893-43-9 simvastatin ammonium salt 

Relevant articles and documents

Furoxan azoxyNO donor type tadine derivative and preparation method thereof (by machine translation)

The invention discloses a furoxan azoxyNO donor type tadine derivative and a preparation method, and belongs to the technical field of chemical synthesis of medicines: the invention has the following structural formula shown in the general formula. Wherein. In addition, coumaric acid is selected as a connecting base, so that the curative effect; in addition, the compound disclosed by the invention can effectively release NO, and beneficial attempts are made for development of NO donor anti-atherosclerotic drugs in an external mode, and the method has the advantages of effectively improving the curative effect of drugs. 4 - R1 R2 (by machine translation)

Lov-D acyltransferase mediated acylation

Methods for the improved acylation of chemical substrates using LovD acyltransferases, thioesters having acyl groups, and (i) thiol scavengers and/or (ii) precipitating agents are presented. An improved method for the production of simvastatin using (i) activated charcoal as a thiol scavenger and/or (ii) ammonium hydroxide as a precipitating agent is also presented.

Parmaceutical

Use of one or more prenylation inhibitors, cholesterol biosynthesis inhibitors or HMG-CoA reductase inhibitors in the manufacture of a medicament for the treatment of hepatitis C virus (HCV) infection. The invention also encompasses a pharmaceutical composition for use in the treatment of HCV infection, the pharmaceutical composition comprising one or more agents capable of inhibiting prenylation, cholesterol biosynthesis or HMG-CoA reductase in the liver, wherein the one or more agents is optionally admixed with a pharmaceutically acceptable carrier, diluent or excipient.