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75330-75-5 molecular structure
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(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 (2S)-2-methylbutanoate

ChemBase ID: 112
Molecular Formular: C24H36O5
Molecular Mass: 404.53964
Monoisotopic Mass: 404.25627425
SMILES and InChIs

SMILES:
O([C@@H]1[C@@H]2[C@H]([C@H](C=CC2=C[C@@H](C1)C)C)CC[C@H]1OC(=O)C[C@H](O)C1)C(=O)[C@H](CC)C
Canonical SMILES:
CC[C@@H](C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
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

Cite this record

CBID:112 http://www.chembase.cn/molecule-112.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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 (2S)-2-methylbutanoate
IUPAC Traditional name
lovastatin
(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 (2S)-2-methylbutanoate
Brand Name
Altocor
Altoprev
Artein
Belvas
Cholestra
Closterol
Colevix
Hipolip
Hipovastin
Lestatin
Lipdip
Lipivas
Lipofren
Lovalip
Lovalord
Lovasterol
Lovastin
Lozutin
Mevacor
Mevinacor
Mevlor
Monacolin K
Nergadan
Paschol
Rodatin
Rovacor
Sivlor
Taucor
Tecnolip
Teroltrat
Synonyms
Lovastatina [Spanish]
Lovastatine [French]
Lovastatinum [Latin]
6 alpha-Methylcompactin
lovastatin
Lovastatin
8-[2-(4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethy l]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthale
(S)-(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-methylbutanoate
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 butanoic acid
6-α-Methylcompactin
Monacolin K
Mevinolin from Aspergillus sp.
(2S)-2-Methylbutanoic Acid (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
(+)-Mevinolin
6α-Methylcompactin
Altocor
Antibiotic MB 530B
L 154803
Lostatin
Lovalip
Lovastatin Lactone
MK 803
MSD 803
Mevacor
Mevinacor
Mevinolin
Mevlor
Monacolin K Lactone
Sivlor
Lipofren
Nergadan
Tancor
lovastatin
(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 (2S)-2-methylbutanoate
洛伐司他汀
CAS Number
75330-75-5
MDL Number
MFCD00072164
PubChem SID
46508223
160963575
24896706
PubChem CID
53232
CHEBI ID
40303
ATC CODE
C10AA02
CHEMBL
503
Chemspider ID
48085
DrugBank ID
DB00227
IUPHAR ligand ID
2739
KEGG ID
D00359
Unique Ingredient Identifier
9LHU78OQFD
Wikipedia Title
Lovastatin
Medline Plus
a688006

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.914537  H Acceptors
H Donor LogD (pH = 5.5) 3.9021869 
LogD (pH = 7.4) 3.9021869  Log P 3.9021869 
Molar Refractivity 113.1824 cm3 Polarizability 44.4169 Å3
Polar Surface Area 72.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.11  LOG S -4.22 
Solubility (Water) 2.43e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.0004 mg/mL expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
Hot Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
152-154°C expand Show data source
166 - 168°C expand Show data source
175°C expand Show data source
Hydrophobicity(logP)
4.082 expand Show data source
4.5 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
EK7907000 expand Show data source
European Hazard Symbols
X expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36/37 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
oral expand Show data source
Bioavailability
<5% expand Show data source
Excretion
negligible expand Show data source
Half Life
1.1-1.7 hours expand Show data source
Metabolism
hepatic (CYP3A substrate) expand Show data source
Protein Bound
>95% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
X (US) expand Show data source
Gene Information
human ... HMGCR(3156)rat ... Hmgcr(25675) expand Show data source
Mechanism of Action
Inhibitor of cholesterol biosynthesis expand Show data source
Potent inhibitor of HMG-CoA expand Show data source
Purity
≥98% (HPLC) expand Show data source
95% expand Show data source
97% expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
Metab. of Aspergillus terreus and Monascus ruber expand Show data source
Application(s)
Antihyperlipidaemic agent expand Show data source
Quality Level
PREMIUM expand Show data source
Empirical Formula (Hill Notation)
C24H36O5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich DrugBank DrugBank Wikipedia Wikipedia TRC TRC
Sigma Aldrich - M2147 external link
Biochem/physiol Actions
Lovastatin is a cholesterol lowering drug and competitive inhibitor of HMG-CoA reductase, a rate limiting enzyme in cholesterol synthesis. Blocks the production of mevalonate, a critical compound in the production of cholesterol and isoprenoids. This product is a substrate of Pgp and CYP3A. It increases cellular resistance to anticancer agents such as doxorubicin and induces apoptosis in myeloma cells. The roles of Pgp and CYP3A, possible connection between drug resistance, regulation of the mevalonate pathway, and iosprenylation of signaling proteins in these observations remain to be resolved. The product induces apoptosis in numerous cancer cell lines perhaps, in part, by inhibiting the isoprenylation of Rho family GTPases. It causes cell cycle arrest in G1 and G2/M phases.
DrugBank - DB00227 external link
Item Information
Drug Groups approved; investigational
Description Lovastatin is a cholesterol-lowering agent that belongs to the class of medications called statins. It was the second agent of this class discovered. It was discovered by Alfred Alberts and his team at Merck in 1978 after screening only 18 compounds over 2 weeks. The agent, also known as mevinolin, was isolated from the fungi Aspergillus terreus. Research on this compound was suddenly shut down in 1980 and the drug was not approved until 1987. Interesting, Akira Endo at Sankyo Co. (Japan) patented lovastatin isolated from Monascus ruber four months before Merck. Lovastatin was found to be 2 times more potent than its predecessor, mevastatin, the first discovered statin. Like mevastatin, lovastatin is structurally similar to hydroxymethylglutarate (HMG), a substituent of HMG-Coenzyme A (HMG-CoA), a substrate of the cholesterol biosynthesis pathway via the mevalonic acid pathway. Lovastatin is a competitive inhibitor of HMG-CoA reductase with a binding affinity 20,000 times greater than HMG-CoA. Lovastatin differs structurally from mevastatin by a single methyl group at the 6’ position. Lovastatin is a prodrug that is activated by in vivo hydrolysis of the lactone ring. It, along with mevastatin, has served as one of the lead compounds for the development of the synthetic compounds used today.
Indication For management as an adjunct to diet to reduce elevated total-C, LDL-C, apo B, and TG levels in patients with primary hypercholesterolemia and mixed dyslipidemia. For primary prevention of coronary heart disease and to slow progression of coronary atherosclerosis in patients with coronary heart disease.
Pharmacology The primary cause of cardiovascular disease is atherosclerotic plaque formation. Sustained elevations of cholesterol in the blood increase the risk of cardiovascular disease. Lovastatin lowers hepatic cholesterol synthesis by competitively inhibiting HMG-CoA reductase, the enzyme that catalyzes the rate-limiting step in the cholesterol biosynthesis pathway via the mevalonic acid pathway. Decreased hepatic cholesterol levels causes increased uptake of low density lipoprotein (LDL) cholesterol and reduces cholesterol levels in the circulation. At therapeutic doses, lovastatin decreases serum LDL cholesterol by 29-32%, increases high density lipoprotein (HDL) cholesterol by 4.6-7.3%, and decrease triglyceride levels by 2-12%. HDL cholesterol is thought to confer protective effects against CV disease, whereas high LDL and triglyceride levels are associated with higher risk of disease.
Toxicity LD50>1000 mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation Undergoes first pass hydrolysis to active metabolites β-hydroxyacid and 6'-hydroxy dervative.
Absorption < 5%. Time to peak serum concentration is 2-4 hours.
Half Life 5.3 hours
Protein Binding > 95%
Elimination Lovastatin undergoes extensive first-pass extraction in the liver, its primary site of action, with subsequent excretion of drug equivalents in the bile. 83% of the orally administered dose is excreted in bile and 10% is excreted in urine.
References
Bobek P, Ozdin L, Galbavy S: Dose- and time-dependent hypocholesterolemic effect of oyster mushroom (Pleurotus ostreatus) in rats. Nutrition. 1998 Mar;14(3):282-6. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - L472225 external link
An antihypercholesterolemic agent. A fungal metabolite, which is a potent inhibitor of HMG-CoA reductase.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bobek P, Ozdin L, Galbavy S: Dose- and time-dependent hypocholesterolemic effect of oyster mushroom (Pleurotus ostreatus) in rats. Nutrition. 1998 Mar;14(3):282-6. Pubmed
  • • Bilheimer, D.W., et al.: Proc. Nat. Acad. Sci. USA, 80, 4124 (1983)
  • • Alberts et al (1980) Mevinolin: a highly potent competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase and a cholesterol-lowering agent. Proc.Natl.Acad.Sci.USA 77 3957.
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PATENTS

PATENTS

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INTERNET

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