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M2537

Sigma-Aldrich

Mevastatin

≥98% (HPLC), powder or crystals

Sinonimo/i:

Compactin, ML-236B

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About This Item

Formula empirica (notazione di Hill):
C23H34O5
Numero CAS:
Peso molecolare:
390.51
Beilstein:
1269441
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

Saggio

≥98% (HPLC)

Forma fisica

powder or crystals

Colore

white to light yellow

Punto di fusione

151 °C

Solubilità

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

Spettro attività antibiotica

neoplastics

Modalità d’azione

enzyme | inhibits

Ideatore

Daiichi-Sankyo

Temperatura di conservazione

2-8°C

Stringa SMILE

[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
AJLFOPYRIVGYMJ-INTXDZFKSA-N

Informazioni sul gene

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Descrizione generale

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

Applicazioni

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

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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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
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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
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