SIMVASTATIN

PRODUCT IDENTIFICATION
CAS NO. 79902-63-9

SIMVASTATIN

EINECS NO.  
FORMULA C25H38O5
MOL WT. 418.57

H.S. CODE

 2932.20.5050

TOXICITY

 Oral Rat LD50: 4438mg/kg
SYNONYMS Simvastatin; Simvastatinum
[(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; Sinvacor; Sivastin; Synvinolin; Vasotenal;  Velostatin; Zocor; Zorced; Zosta; Cholestat; Coledis; Colemin; Corolin; 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]-(4R,6R)-1-naphthalenyl ester;
SMILES C1[C@H](OC(=O)C[C@@H]1O)CC[C@@H]1[C@H]2[C@@H] (OC(C(CC)(C)C)=O)C[C@@H](C)C=C2C=C[C@@H]1C

CLASSIFICATION

Anticholesteremic, Antihyperlipidemic, Antilipemic, Hydroxymethylglutaryl-CoA reductase inhibitor, Hypolipidemic, Lipid Regulator

EXTRA NOTES

 A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE white to off-white crystalline powder
MELTING POINT 135 - 138 C
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER Insoluble
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

log P 4.68(Octanol-water)
VAPOR PRESSURE 6.41E-13 (mmHg at 25 C)
HENRY LAW CONSTANT 2.81E-10 (atm-m3/mole at 25 C)
OH RATE CONSTANT 2.29E-10 (cm3/molecule-sec at 25 C Atmospheric)

NFPA RATINGS

Health: 1, Flammability: 0, Reactivity: 0

REFRACTIVE INDEX

  
FLASH POINT

 

STABILITY Stable under ordinary conditions.

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Simvastatin

PubChem Compound Summary - Simvastatin

Drug Bank - Simvastatin

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Simvastatin

http://www.hcc.bcu.ac.uk/
The beneficial effects of statins are the result of their capacity to reduce cholesterol biosyntesis, mainly in the liver, where they are selectively distributed, as well as to the modulation of lipid metabolism, derived from their effect of inhibition upon HMG-CoA reductase. Statins have antiatherosclerotic effects, that positively correlate with the percent decrease in LDL cholesterol. In addition, they can exert antiatherosclerotic effects independently of their hypolipidemic action. Because the mevalonate metabolism generates a series of isoprenoids vital for different cellular functions, from cholesterol synthesis to the control of cell growth and differentiation, HMG-CoA reductase inhibition has beneficial pleiotropic effects. Consequently, statins reduce significantly the incidence of coronary events, both in primary and secondary prevention, being the most efficient hypolipidemic compounds that have reduced the rate of mortality in coronary patients. Independent of their hypolipidemic properties, statins interfere with events involved in bone formation and impede tumor cell growth.

http://www.sigmaaldrich.com/
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).

Local

statins (or hydroxymethylglutaryl coenzyme A reductase inhibitors)

Statin

CAS RN.

Mevastatin

73573-88-3
Lovastatin 75330-75-5
Simvastatin 79902-63-9
Pravastatin 81093-37-0
Fluvastatin 93957-54-1
Fluvastatin Sodium 93957-55-2
Atorvastatin 134523-00-5
Atorvastatin Calcium 134523-03-8
Cerivastatin Sodium 143201-11-0
Cerivastatin 145599-86-6
Pitavastatin 147511-69-1
Rosuvastatin 287714-41-4

 
SALES SPECIFICATION

APPEARANCE

 white to off-white crystalline powder

ASSAY

 98.0 - 101.0%

MELTING POINT

134 - 136 C

LOSS ON DRYING

0.5% max

IMPURITY

Total impurity: 0.5% max
Individual Impurity: 0.2% max
RESIDUE ON IGNITION

0.2% max
TRANSPORTATION
PACKING

 

HAZARD CLASS  
UN NO. Not regulated
SAFETY INFORMATION

Hazard OVERVIEW

Not known

GHS

 
SIGNAL WORD Warning

PICTOGRAMS

None

HAZARD STATEMENTS

H303 May be harmful if swallowed.
EC DIRECTIVES

 
HAZARD CODES

 

SAFETY PHRASES

22 -24/25

PRICE INFORMATION