Tenivastatin sodium

Base Information

• Chemical Name: Tenivastatin sodium
• CAS No.: 101314-97-0
• Molecular Formula: C25H39NaO6
• Molecular Weight: 458.56
• European Community (EC) Number: 641-864-4
• UNII: 2L6JSY5YGL
• ChEMBL ID: CHEMBL487720
• Nikkaji Number: J428.165I
• Wikidata: Q27254885
• Mol file: 101314-97-0.mol

Synonyms:Tenivastatin sodium;simvastatin sodium;101314-97-0;Simvastatin Hydroxy Acid Sodium Salt;Simvastatin, Sodium Salt;2L6JSY5YGL;J428.165I;CHEMBL487720;Simvastatin hydroxy acid (sodium);sodium (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-dihydroxyheptanoate;Simvastatin (sodium);UNII-2L6JSY5YGL;Simvastatin sodium?;simvastatinsodiumsalt;SCHEMBL10390708;RLWRROYWKHUVKF-OKDJMAGBSA-M;BDBM50455629;(betaR,deltaR,1S,2S,6R,8S,8aR)-8-(2,2-Dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2,6-dimethyl-1-naphthaleneheptanoic acid, monosodium salt;1-Naphthaleneheptanoic acid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2,6-dimethyl-, monosodium salt, (betaR,deltaR,1S,2S,6R,8S,8aR)-;PD015663;HY-115292;CS-0034900;J-000363;Q27254885;(.BETA.R,.DELTA.R,1S,2S,6R,8S,8AR)-8-(2,2-DIMETHYL-1-OXOBUTOXY)-1,2,6,7,8,8A-HEXAHYDRO-.BETA.,.DELTA.-DIHYDROXY-2,6-DIMETHYL-1-NAPHTHALENEHEPTANOIC ACID, MONOSODIUM 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;1-Naphthaleneheptanoic acid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-.beta.,.delta.-dihydroxy-2,6-dimethyl-, monosodium salt, (.beta.R,.delta.R,1S,2S,6R,8S,8aR)-;Simvastatin Imp. A (EP);Simvastatin Imp. A (EP) as Sodium Salt;Tenivastatin Sodium Salt;Simvastatin Impurity A as Sodium Salt;sodium;(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

Chemical Property of Tenivastatin sodium

Chemical Property:

• PSA: 106.89000
• LogP: 2.88350
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 458.26443324
• Heavy Atom Count: 32
• Complexity: 701

Purity/Quality:

98%Min ^*data from raw suppliers

SimvastatinHydroxyAcidSodiumSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)[O-])O)O)C.[Na+]
• 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](C[C@H](CC(=O)[O-])O)O)C.[Na+]
• 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.

Technology Process of Tenivastatin sodium

There total 7 articles about Tenivastatin sodium 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:

Reference yield: 77.8%

simvastatin (123049-81-0,79902-63-9) → simvastatin sodium salt (101314-97-0)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; acetone; acetonitrile;

Reference yield:

simvastatin → simvastatin sodium salt (101314-97-0)

Guidance literature:

With sodium hydroxide; In acetone; at 20 ℃; for 4h;

Reference yield:

methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate (938063-63-9) + (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 (132748-10-8) → simvastatin sodium salt (101314-97-0)

Guidance literature:

(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; With sodium hydroxide; In water; at 25 ℃;

With hydrogenchloride; LovD acyltransferase; pyrographite; In water; at 25 ℃; for 0.0833333h; Enzymatic reaction;

methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate; In water; at 25 ℃; Enzymatic reaction;

upstream raw materials:

simvastatin

2,2-dimethylbutanoyl chloride

methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate

(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

Downstream raw materials:

simvastatin ammonium salt

Refernces

• 1、 -. "Furoxan azoxyNO donor type tadine derivative and preparation method thereof (by machine translation)". Paragraph 0110; 0118-0121. . Retrieved 2019/10/01.
• 2、 -. "COMPOSITIONS AND TREATMENTS FOR INHIBITING KINASE AND/OR HMG-COA REDUCTASE". Page/Page column 53. . Retrieved 2008/06/13.