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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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
- 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/s1InChIKey
PCZOHLXUXFIOCF-BXMDZJJMSA-NSmiles
CC[C@H](C)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.