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Substance Name: Lovastatin [USAN:USP:INN:BAN]
RN: 75330-75-5
UNII: 9LHU78OQFD
InChIKey: PCZOHLXUXFIOCF-BXMDZJJMSA-N

Note

  • A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.

Molecular Formula

  • C24-H36-O5

Molecular Weight

  • 404.543
 

Classification Codes

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

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Lovastatin

Synonyms

  • (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 (S)-2-methyl-butyrate
  • (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-2-Methylbutanoic acid 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
  • (S)-2-Methylbutyric 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
  • 1,2,6,7,8,8a-Hexahydro-beta,delta-dihydroxy-2,6-dimethyl-8-(2-methyl-1-oxobutyoxy)-1-naphthaleneheptanoic acid delta-lactone
  • 2beta,6alpha-Dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactone
  • 6-alpha-Methylcompactin
  • 6alpha-Methylcompactin
  • Altocor
  • Altoprev
  • Artein
  • Belvas
  • BRN 3631989
  • Butanoic acid, 2-methyl-, 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(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-
  • CCRIS 8092
  • Cholestra
  • Closterol
  • Colevix
  • EC 616-212-7
  • Hipolip
  • Hipovastin
  • HSDB 6534
  • Lestatin
  • Lipdip
  • Lipivas
  • Lipofren
  • Lovalip
  • Lovalord
  • Lovastatin
  • Lovastatina
  • Lovastatina [Spanish]
  • Lovastatine
  • Lovastatine [French]
  • Lovastatinum
  • Lovastatinum [Latin]
  • Lovasterol
  • Lovastin
  • Lozutin
  • Mevacor
  • Mevinacor
  • Mevinolin
  • Mevlor
  • MK 803
  • MK-803
  • Monacolin K
  • MSD 803
  • Nergadan
  • NSC 758662
  • Paschol
  • Rodatin
  • Rovacor
  • Sivlor
  • Taucor
  • Tecnolip
  • Teroltrat
  • UNII-9LHU78OQFD

Systematic Names

  • (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-8-(2-((4R,6R)-4-hydroxy-2-oxo-2H-pyran-6-yl)ethyl)-3,7-dimethylnaphtyl(S)-2-methylbutyrat
  • Butanoic acid, 2-methyl-, (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, (2S)-
  • Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-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, (2S)-
  • Butanoic acid, 2-methyl-, 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(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-
  • Monacolin K

Superlist Name

  • Lovastatin

Registry Numbers

CAS Registry Number

  • 75330-75-5

FDA UNII

  • 9LHU78OQFD

Other Registry Numbers

  • 71949-96-7
  • 74133-25-8
  • 81739-26-6

System Generated Number

  • 0075330755

Structure Descriptors

InChI

InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

InChIKey

PCZOHLXUXFIOCF-BXMDZJJMSA-N

Smiles

CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H]12

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 17mg/kg/3W-I (17mg/kg) BEHAVIORAL: WAKEFULNESS Lancet. Vol. 343, Pg. 973, 1994.
human TDLo oral 8750ug/kg/14D (8.75mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: WAKEFULNESS		 Clinical Pharmacology and Therapeutics Vol. 50, Pg. 730, 1991.
man TDLo oral 240mg/kg/60W- (240mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Annals of Pharmacotherpy. Vol. 26, Pg. 190, 1992.
mouse LD50 oral > 1gm/kg (1000mg/kg)   Journal of Antibiotics. Vol. 32, Pg. 852, 1979.
women TDLo oral 285mg/kg/30W- (285mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: LIVER FUNCTION TESTS IMPAIRED		 Israel Journal of Medical Sciences. Vol. 28, Pg. 101, 1992.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 4.26 (none)   EXP
Water Solubility 2.140 mg/L 25 EST
Vapor Pressure 1.34E-12 mm Hg 25 EST
Henry's Law Constant 2.12E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.30E-10 cm3/molecule-sec 25 EST

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