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M2537 Sigma-Aldrich

Mevastatin

≥98% (HPLC), powder or crystals

Synonym: Compactin, ML-236B

  • CAS Number 73573-88-3

  • Empirical Formula (Hill Notation) C23H34O5

  • Molecular Weight 390.51

  •  Beilstein/REAXYS Number 1269441

  •  MDL number MFCD05662341

  •  PubChem Substance ID 24278540

  •  NACRES NA.77

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Mechanism of Action,
Quality Level   200
assay   ≥98% (HPLC)
form   powder or crystals
color   white to light yellow
mp   151  °C
solubility   ethanol: 25-26 mg/mL, clear, colorless
Mode of action   enzyme | inhibits
antibiotic activity spectrum   neoplastics
originator   Daiichi-Sankyo
storage temp.   2-8°C
SMILES string   [H][C@]12[C@H](CCC=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/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
InChI key   AJLFOPYRIVGYMJ-INTXDZFKSA-N
Gene Information   human ... HMGCL(3155), HMGCR(3156)
rat ... Hmgcr(25675)

Description

General description

Chemical structure: statin

Biochem/physiol Actions

HMG-CoA reductase inhibitor. Cholesterol lowering drug. Inhibits myoblast formation. An antibiotic shown to cause apoptosis, apparently by inhibiting post-translational prenylation of proteins such as Ras. Similarly, mevastatin increases eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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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 Lipid Signaling Research

Within mammalian cells, a multitude of lipid compounds are found with a variety of cellular functions, including structural components of cell membranes and as second messengers in cell signaling pat...
Keywords: Absorption, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell signaling, Diabetes, Digestions, Diseases, Growth factors, Hormones, Inflammation, Lipid Metabolism, Lipid signaling, Metabolism

Peer-Reviewed Papers
15

References

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