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Basic information

  • Name:

  • Simvastatin

  • CAS No.:

  • 79902-63-9

  • Formula:
  • C25H38O5
  • 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;

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Chemistry

Molecular structure of Simvastatin (CAS NO.79902-63-9) is:

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 
Molecular Weight: 418.56622 g/mol
Molecular Formula: C25H38O5  
XLogP3: 4.7
H-Bond Donor: 1
H-Bond Acceptor: 5 
Index of Refraction: 1.53
Molar Refractivity: 116.37 cm3
Molar Volume: 376.5 cm3
Melting Point: 139 °C
Surface Tension: 43 dyne/cm
Density: 1.11 g/cm3
Flash Point: 184.8 °C
Enthalpy of Vaporization: 97.49 kJ/mol
Boiling Point: 564.9 °C at 760 mmHg
Vapour Pressure: 4.12E-15 mmHg at 25 °C
Classification Code: Anticholesteremic agents; Antihyperlipidemic; Antilipemic agents; Antimetabolites; Drug / Therapeutic Agent; Enzyme Inhibitors; Human Data; Hydroxymethylglutaryl-CoA reductase inhibitors; Reproductive Effect

History

In 1956, mevalonic acid was isolated from a yeast extract by Karl Folkers.
In 1959, the HMG-CoA reductase enzyme was discovered by researchers at the Max Planck Institute.
By 1976, Akira Endo had isolated the first inhibitor (Compactin, ML-236B) from the fungus, Penicillium citrinium in Sankyo, Japan.
In 1979, Hoffman and colleagues isolated lovastatin from a strain of the fungus Aspergillus terreus.

Uses

 Simvastatin (CAS NO.79902-63-9) is used to control hypercholesterolemia and to prevent cardiovascular disease. It is a powerful lipid-lowering drug that can decrease low density lipoprotein (LDL) levels by up to 50%.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
mouse LD50 intraperitoneal 798mg/kg (798mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
mouse LD50 oral 3gm/kg (3000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES		 Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
mouse LD50 subcutaneous 1009mg/kg (1009mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
rat LD50 intraperitoneal 705mg/kg (705mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
rat LD50 oral 4438mg/kg (4438mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES		 Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
rat LD50 subcutaneous 672mg/kg (672mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
women LDLo oral 108mg/kg/77W- (108mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 Australian and New Zealand Journal of Medicine. Vol. 25, Pg. 745, 1995.
women TDLo oral 2800ug/kg/7D- (2.8mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: LIVER FUNCTION TESTS IMPAIRED		 Medical Journal of Australia. Vol. 155, Pg. 61, 1991.

Safety Profile

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

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.

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