• USA Home
  • M2147 - Mevinolin from Aspergillus sp.

EMAIL THIS PAGE TO A FRIEND
M2147 Sigma-Aldrich

Mevinolin from Aspergillus sp.

≥98% (HPLC)

Synonym: 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, Lovastatin, Monacolin K

  • CAS Number 75330-75-5

  • Empirical Formula (Hill Notation) C24H36O5

  • Molecular Weight 404.54

  •  MDL number MFCD00072164

  •  PubChem Substance ID 24896706

  •  NACRES NA.77

Purchase

Properties

Related Categories Abbott, Antitumor Agents, Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index,
Quality Level   300
assay   ≥98% (HPLC)
solubility   ethanol: 9.80-10.20 mg/mL, clear, colorless to faintly yellow
originator   Abbott
storage temp.   2-8°C
SMILES string   [H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(=O)O3)OC(=O)[C@@H](C)CC
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
InChI key   PCZOHLXUXFIOCF-BXMDZJJMSA-N
Gene Information   human ... HMGCR(3156)
rat ... Hmgcr(25675)

Description

Packaging

25 mg in glass bottle

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.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
EK7907000

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number
Protocols & Articles

Articles

Antilipemic Agents

Randomized controlled clinical studies have suggested 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors (statins) are effective in both primary and secondary prevention of cardiova...
Sami Barghshoon
BioFiles v7 n5, 2012, 21–24
Keywords: Anti-inflammatory agents, Cardiovascular, Chemical vapor deposition, Clinical, Diabetes, Inflammation, Oxidations, Transcription

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. When dietary intake of cholesterol is high, synthesis is decreased and when dietary inta...
BioFiles 2007, 2.7, 6.
Keywords: Gene expression, Transcription

Dietary Terpenes

Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.1 While the enzymes responsible for terpene synthesis are fo...
BioFiles 2008, 3.9, 4.
Keywords: Anti-inflammatory agents, Antimicrobials, Antiparasitics, Apoptosis, Building blocks, Cancer, Carcinogens, Cell division, Condensations, Detergents, Gene expression, Hormones, Insecticides, Isomerizations, Metabolites, Neurotransmitters, Poisons, Pollination, Reproduction, Vitamins

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

Related Content

Carcinogen Selector - Digestive System - Liver

From our library of Related Content, Sigma-Aldrich presents Carcinogen Selector - Digestive System - Liver
Keywords: Cancer, Carcinogens, Respiratory

Carcinogen Selector - Digestive System - Stomach

From our library of Related Content, Sigma-Aldrich presents Carcinogen Selector - Digestive System - Stomach
Keywords: Cancer, Carcinogens, Respiratory

Carcinogen Selector - Digestive System

From our library of Related Content, Sigma-Aldrich presents Carcinogen Selector - Digestive System
Keywords: Cancer, Carcinogens, Respiratory

Carcinogen Selector - Endocrine System - Liver Endocrine

The Carcinogen Selector gives researchers the ability to select carcinogens by the mouse organs that they promote cancer in. The tool includes over 750 carcinogens that target 35 specific organs acro...
Keywords: Cancer, Carcinogens, Respiratory

Carcinogen Selector - Endocrine System

The Carcinogen Selector gives researchers the ability to select carcinogens by the mouse organs that they promote cancer in. The tool includes over 750 carcinogens that target 35 specific organs acro...
Keywords: Cancer, Carcinogens, Respiratory

Carcinogen Selector - Reproductive System - Lung

The Carcinogen Selector gives researchers the ability to select carcinogens by the mouse organs that they promote cancer in. The tool includes over 750 carcinogens that target 35 specific organs acro...
Keywords: Cancer, Carcinogens, Respiratory

Carcinogen Selector - Respiratory System

The Carcinogen Selector gives researchers the ability to select carcinogens by the mouse organs that they promote cancer in. The tool includes over 750 carcinogens that target 35 specific organs acro...
Keywords: Cancer, Carcinogens, Respiratory

Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?