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Merck

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:
Peso molecular:
390.51
Beilstein:
1269441
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

Análisis

≥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

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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)


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
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
R Chakravarti et al.
Applied microbiology and biotechnology, 64(5), 618-624 (2004-03-23)
Compactin, a hypocholesterolemic molecule, is a competitive inhibitor of 3-hydroxy-3-methyl-glutaryl (HMG)-CoA reductase, which is a regulatory enzyme for cholesterol biosynthesis. The structural similarity and high affinity of the acid form of compactin and HMG, the natural substrate of enzyme, results
Ml Pinzón-Daza et al.
British journal of pharmacology, 167(7), 1431-1447 (2012-07-14)
The passage of drugs across the blood-brain barrier (BBB) limits the efficacy of chemotherapy in brain tumours. For instance, the anticancer drug doxorubicin, which is effective against glioblastoma in vitro, has poor efficacy in vivo, because it is extruded by

Artículos

Cholesterol synthesis regulation by dietary levels, LDL receptors control lipid-rich LDL particle transport in cells.

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