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M2537

Sigma-Aldrich

Mevastatin

≥98% (HPLC), powder or crystals

Sinônimo(s):

Compactin, ML-236B

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5 MG
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5 MG
R$ 1.361,00

About This Item

Fórmula empírica (Notação de Hill):
C23H34O5
Número CAS:
Peso molecular:
390.51
Beilstein:
1269441
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

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Ensaio

≥98% (HPLC)

Formulário

powder or crystals

cor

white to light yellow

pf

151 °C

solubilidade

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

espectro de atividade do antibiótico

neoplastics

Modo de ação

enzyme | inhibits

originador

Daiichi-Sankyo

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

AJLFOPYRIVGYMJ-INTXDZFKSA-N

Informações sobre genes

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Descrição geral

Chemical structure: statin
Mevastatin is a polyketide that belongs to the class of statins. It contains a hydroxy-hexahydronaphthalene ring.[1]

Aplicação

Mevastatin has been used:
  • to analyze its effects on chronic lymphocytic leukemia (CLL) cells by cytotoxic assay[2]
  • as a prenylation inhibitor to analyze its effects on human embryonic kidney (HEK) cells transfected with K-Ras[3]
  • as a statin agent to study its anti-cancer effect on human breast cancer cells and glioblastoma in vitro[4]

Ações bioquímicas/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.[1] 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.[5] Mevastatin increases endothelial nitric oxide synthase (eNOS) mRNA and protein levels by blocking the geranylgeranylation of transcription factor Rho.[6]

Características e benefícios

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

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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Visite a Biblioteca de Documentos

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
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
Nathan J Schuld et al.
The Journal of biological chemistry, 289(10), 6862-6876 (2014-01-15)
Ras family small GTPases localize at the plasma membrane, where they can activate oncogenic signaling pathways. Understanding the mechanisms that promote membrane localization of GTPases will aid development of new therapies to inhibit oncogenic signaling. We previously reported that SmgGDS

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