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Substance Name: Simvastatin [USAN:USP:INN:BAN]
RN: 79902-63-9
UNII: AGG2FN16EV
InChIKey: RYMZZMVNJRMUDD-HGQWONQESA-N

Note

  • 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.

Molecular Formula

  • C25-H38-O5

Molecular Weight

  • 418.57
 

Classification Codes

  • Anticholesteremic Agents
  • Antihyperlipidemic
  • Antimetabolites
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • Hypolipidemic Agents
  • Lipid Regulating Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Simvastatin
  • Simvastatin [USAN:USP:INN:BAN]

MeSH Heading

  • Simvastatin

Synonyms

  • 2,2-Dimethylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one
  • BRN 4768037
  • 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))-
  • CCRIS 7558
  • Cholestat
  • Coledis
  • Colemin
  • Corolin
  • Denan
  • DRG-0320
  • HSDB 7208
  • L 644128-000U
  • Labistatin
  • Lipex
  • Lodales
  • Medipo
  • MK 0733
  • MK-0733
  • MK-733
  • Nivelipol
  • Pantok
  • Rechol
  • Rendapid
  • Simovil
  • Simvastatin
  • Simvastatina
  • Simvastatina [Spanish]
  • Simvastatine
  • Simvastatine [French]
  • Simvastatinum
  • Simvastatinum [Latin]
  • Sinvacor
  • Sivastin
  • Synvinolin
  • UNII-AGG2FN16EV
  • Vasotenal
  • Velostatin
  • Zocor
  • Zorced
  • Zosta

Systematic Names

  • 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
  • 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

Mixture Name

  • Vytorin

Registry Numbers

CAS Registry Number

  • 79902-63-9

FDA UNII

  • AGG2FN16EV

System Generated Number

  • 0079902639

Structure Descriptors

InChI

1S/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-HGQWONQESA-N

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

Toxicity

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) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Oyo Yakuri. Pharmacometrics. Vol. 39, Pg. 95, 1990.
mouse LD50 oral 3gm/kg (3000mg/kg) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
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) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Australian and New Zealand Journal of Medicine. Vol. 25, Pg. 745, 1995.
women TDLo oral 2800ug/kg/7D- (2.8mg/kg)   Medical Journal of Australia. Vol. 155, Pg. 61, 1991.
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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 135-138 deg C   EXP
log P (octanol-water) 4.68 (none)   EXP
Water Solubility 0.765 mg/L 25 EST
Vapor Pressure 6.41E-13 mm Hg 25 EST
Henry's Law Constant 2.81E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.29E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.