Related Searches: Simvastatin

Simvastatin(CAS No. 79902-63-9)

Simvastatin C25H38O5 (cas 79902-63-9) Molecular Structure

79902-63-9 Structure

Identification and Related Records

【Name】
Simvastatin
【Iupac name】
[(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
【CAS Registry number】
79902-63-9
【Synonyms】
Butanoic acid,2,2-dimethyl-,(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]-1-naphthalenyl ester
Colemin
Nivelipol
Butanoic acid, 2,2-dimethyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha,3alpha,7beta,8beta(2S*,4S*),8abeta))-
Simvastatin [USAN:BAN:INN]
Velostatin
Coledis
MK-733
Medipo
MK 0733
Simvastatin (COS)
MK-0733
Labistatin
Simvastatine [French]
Zocor (TN)
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
Sivastin
Rendapid
Synvinolin
Corolin
Butanoic acid, 2,2-dimethyl-, (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)-1-naphthalenyl ester
Liponorm
Lodales
Pantok
[(1S,3R,7R,8S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxo-oxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
Lipex
Vasotenal
【EINECS(EC#)】
404-520-2
【Molecular Formula】
C25H38O5 (Products with the same molecular formula)
【Molecular Weight】
418.57
【Inchi】
InChI=1/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
【InChIKey】
RYMZZMVNJRMUDD-UHFFFAOYSA-N
【Canonical SMILES】
CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
【Isomers 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
【MOL File】
79902-63-9.mol

Chemical and Physical Properties

【Appearance】
white to off- white crystalline powder
【Density】
1.11 g/cm3
【Melting Point】
139 °C
【Boiling Point】
564.9 °C at 760 mmHg
【Refractive Index】
1.53
【Flash Point】
184.8 °C
【Water】
Soluble in DMSO (>25 mg/mL) and ethanol (>25 mg/mL)
【Solubilities】
Soluble in DMSO (>25 mg/mL) and ethanol (>25 mg/mL)
【Color/Form】
Crystals from n-butyl chloride + hexane
White to off-white crystalline powder
【Storage temp】
0-6°C
【Spectral properties】
UV max (acetonitrile): 231, 238, 247 nm (A(1% 1 cm) = 516, 604, 408, respectively)
【Computed Properties】
Molecular Weight:418.56622 [g/mol]
Molecular Formula:C25H38O5
XLogP3:4.7
H-Bond Donor:1
H-Bond Acceptor:5
Rotatable Bond Count:7
Tautomer Count:2
Exact Mass:418.271924
MonoIsotopic Mass:418.271924
Topological Polar Surface Area:72.8
Heavy Atom Count:30
Formal Charge:0
Complexity:706
Isotope Atom Count:0
Defined Atom Stereocenter Count:7
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:3
Effective Rotor Count:9
Conformer Sampling RMSD:1
CID Conformer Count:52

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R36/37/38
【Safety Statements 】
26-36
【HazardClass】
9
【Safety】

Safty information about Simvastatin (CAS NO.79902-63-9) is:
Hazard Codes:?IrritantXi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
RIDADR: 3077
RTECS: EK7798000
HazardClass: 9
PackingGroup: III

【PackingGroup 】
III
【Transport】
3077
【Formulations/Preparations】
Oral: Tablets, film coated: 5 mg Zocor (Merck); 10 mg Zocor (Merck); 20 mg Zocor (Merck); 40 mg Zocor (Merck); 80 mg Zocor (Merck).
Trade names: Denan, Liponorm, Lodales, Simovil, Sinvacor, Sivastin, Zocor, Zocord
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl simvastatin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

?Simvastatin , its cas register number is 79902-63-9. It also can be called?[(1S,3R,7R,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-oxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoat ; Butanoic acid, 2,2-dimethyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro- 4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1-alpha,3-alpha,7- beta,8-beta(2S*,4S*),8a-beta)) ; L-644128-000U ; MK-0733 ; Zocor .It is a?white powder.

【Octanol/Water Partition Coefficient】
log Kow = 4.68
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Usage】

A competitive inhibitor of HMG-CoA reductase. A synthetic analog of lovastatin

Biomedical Effects and Toxicity

【Biological Activity】
HMG-CoA reductase inhibitor; decreases levels of low density lipoprotein. Has multiple biological effects including bone formation stimulation, inhibition of smooth muscle cell proliferation and migration, and anticancer and anti-inflammatory activity.
【Pharmacological Action】
- Substances used to lower plasma cholesterol levels.
- Compounds that inhibit HMG-CoA reductases. They have been shown to directly lower cholesterol synthesis.
- Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
【Therapeutic Uses】
Antihyperlipidemic
Simvastatin /is/ indicated as adjunctive therapy with other lipid lowering treatments (eg, LDL apheresis) in homozygous familial hypercholesterolemia to reduce total cholesterol (total-C) and LDL-C. /Included in US product labeling/
... Simvastatin /is/ indicated as adjunctive therapy to diet for the treatment of patients with elevated serum triglyceride levels (type IV hyperlipoproteinemia). /Included in US product labeling/
... Simvastatin /is/ indicated for the treatment of dysbetalipopreteinemia (type III hyperlipoproteinemia) in patients who did not respond adequately to diet. /Included in US product labeling/
... Simvastatin /is/ indicated to reduce the risk of total mortality by reducing the incidence of coronary death in patients without symptomatic cardiovascular disease. ... Simvastatin /is/ indicated to reduce the risk of myocardial infarction and the risk of undergoing myocardial revascularization procedures. ... /Included in US product labeling/
Simvastatin is indicated to reduce the risk of stroke or transient ischemic attack in patients with coronary heart disease and hypercholesterolemia. /Included in US product labeling/
Clinical trial evidence strongly favors aggressive risk factor modification in the prevention of coronary artery disease (CAD). The latest landmark trial of therapy using a 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor (statin) is the Heart Protection Study (HPS) of simvastatin versus placebo in a cohort of patients at high risk for CAD. The HPS reported a number of highly significant reductions in the risk for major vascular events with treatment. It also provides new insights into the effects of statin therapy in patient subgroups, such as the elderly, women, and those with noncoronary vascular disease. These data are likely to have an important influence on the future of cardiovascular disease prevention.
The MRC/BHF Heart Protection Study included 5963 participants with diabetes, of whom 2912 had no history of vascular disease at baseline. Patients were randomized to 40 mg simvastatin daily or matching placebo for 5 years, which, on average, reduced LDL by 1.0 mmol/l compared with placebo. Highly significant reductions of about one-quarter in major vascular events were seen both overall and in different types of patient with diabetes, including those with average and below average lipid levels. Recent data from the Antihypertensive and Lipid-Lowering Treatment to Prevent Heart Attack Trial and the Anglo-Scandinavian Cardiac Outcomes Trial support these findings and are consistent with these effects. SUMMARY: Good quality, randomized trials including substantial numbers of patients with diabetes show that such patients obtain the same proportional benefit as other groups studied. Given their increased cardiovascular risk, these findings argue for a simple strategy of considering routine statin therapy for patients with type 2 diabetes and adult patients with type 1 diabetes, irrespective of lipid levels. As generic statins become available this could have a greater impact on the burden of cardiovascular disease in diabetes than restricted and targeted therapy. [Armitage J, Bowman L; Curr Opin Lipidol 15 (4): 439-46 (2004)]
【Biomedical Effects and Toxicity】
In animals studies, after oral dosing, simvastatin achieved substantially higher concentrations in the liver than in non-target tissues. Simvastatin undergoes extensive first-pass extraction in the liver, its primary site of action, with subsequent excretion of drug equivalents in the bile. As a consequence of extensive hepatic extraction of simvastatin (estimated to be > 60% in man), the availability of drug to the general circulation is low. In a single-dose study in nine healthy subjects, it was estimated that less than 5% of an oral dose of simvastatin reaches the general circulation as active inhibitors.
Elimination: Fecal (biliary and unabsorbed): 60%; Renal: 13%.
Absorption in animal study averaged about 85%; bioavailability less than 5%.
It is not known whether simvastatin is distributed into human breast milk.
Following an oral dose of 14(C)-labeled simvastatin in man, 13% of the dose was excreted in urine and 60% in feces. The latter represents absorbed drug equivalents excreted in bile, as well as any unabsorbed drug.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8,400(SRC), determined from a log Kow of 4.68(2) and a regression-derived equation(3), indicates that simvastatin is expected to be immobile in soil(SRC). Volatilization of simvastatin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Simvastatin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-13 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8,400(SRC), determined from a log Kow of 4.68(2) and a regression-derived equation(3), indicates that simvastatin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.8X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 800(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data were not available.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), simvastatin, which has an estimated vapor pressure of 6.4X10-13 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase simvastatin may be removed from the air by wet and dry deposition(SRC).

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