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M2537

Sigma-Aldrich

Mevastatin

≥98% (HPLC), powder or crystals

Sinónimos:

Compactin, ML-236B

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About This Item

Fórmula empírica (notación de Hill):
C23H34O5
Número de CAS:
73573-88-3
Peso molecular:
390.51
Beilstein:
1269441
Número MDL:
MFCD05662341
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24278540
NACRES:
NA.77

Ensayo

≥98% (HPLC)

Formulario

powder or crystals

color

white to light yellow

mp

151 °C

solubilidad

ethanol: 25-26 mg/mL, clear, colorless

espectro de actividad antibiótica

neoplastics

Modo de acción

enzyme | inhibits

emisor

Daiichi-Sankyo

temp. de almacenamiento

2-8°C

cadena SMILES

[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

Clave InChI

AJLFOPYRIVGYMJ-INTXDZFKSA-N

Información sobre el gen

human ... HMGCL(3155) , HMGCR(3156)
rat ... Hmgcr(25675)

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Descripción general

Chemical structure: statin
Mevastatin is a polyketide that belongs to the class of statins. It contains a hydroxy-hexahydronaphthalene ring.

Aplicación

Mevastatin has been used:
  • to analyze its effects on chronic lymphocytic leukemia (CLL) cells by cytotoxic assay
  • as a prenylation inhibitor to analyze its effects on human embryonic kidney (HEK) cells transfected with K-Ras
  • as a statin agent to study its anti-cancer effect on human breast cancer cells and glioblastoma in vitro

Acciones bioquímicas o fisiológicas

Mevastatin is a selective inhibitor of 3-hydroxy 3-methyl glutaryl coenzyme(A) reductase (HMG-CoA reductase), a major enzyme involved in cholesterol synthesis. It acts as a cholesterol-lowering agent. Mevastatin is obtained from various species of fungi. It acts as an antiresorptive agent and has therapeutic effects to treat osteoporosis. Mevastatin inhibits bone resorption by triggering osteoclast apoptosis. It is also involved in the inhibition of prenylation of proteins such as Ras. Mevastatin increases endothelial nitric oxide synthase (eNOS) mRNA and protein levels by blocking the geranylgeranylation of transcription factor Rho.

Características y beneficios

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

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
049M4755V
048M4833V
126M4789V
086M4819V
056M4775V

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Visite la Librería de documentos

C M Shipman et al.
Cancer research, 58(23), 5294-5297 (1998-12-16)
It has recently been suggested that bisphosphonates may have direct antitumor effects in vivo, in addition to their therapeutic antiresorptive properties. Bisphosphonates can inhibit proliferation and cause apoptosis in human myeloma cells in vitro. In macrophages, bisphosphonate-induced apoptosis was recently
F P Coxon et al.
Molecular pharmacology, 54(4), 631-638 (1998-10-10)
The exact mechanisms of action of antiresorptive bisphosphonate drugs remain unclear, although they may inhibit bone resorption by mechanisms that can lead to osteoclast apoptosis. These drugs also cause apoptosis in J774 macrophages, probably as a consequence of inhibition of
J T Woo et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 15(4), 650-662 (2000-04-26)
Compactin (mevastatin), which inhibits 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, and thus biosynthesis of cholesterol and the prenylation of proteins, inhibits osteoclastic bone resorption. Although it has been suggested that compactin inhibits bone resorption by inducing apoptosis of osteoclasts, the pathway by
U Laufs et al.
The Journal of biological chemistry, 273(37), 24266-24271 (1998-09-03)
The mechanism by which 3-hydroxy-3-methylglutaryl (HMG)-CoA reductase inhibitors increase endothelial nitric oxide synthase (eNOS) expression is unknown. To determine whether changes in isoprenoid synthesis affects eNOS expression, human endothelial cells were treated with the HMG-CoA reductase inhibitor, mevastatin (1-10 microM)
S P Luckman et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 13(4), 581-589 (1998-04-29)
Bisphosphonates are currently the most important class of antiresorptive drugs used for the treatment of metabolic bone diseases. Although the molecular targets of bisphosphonates have not been identified, these compounds inhibit bone resorption by mechanisms that can lead to osteoclast
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Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. LDL receptors regulate the cellular transport of lipid rich low density lipoprotein (LDL) particles.

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 cardiovascular disease (CVD) events.

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