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M2537

Sigma-Aldrich

Mevastatin

≥98% (HPLC), powder or crystals

Synonyme(s) :

Compactin, ML-236B

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About This Item

Formule empirique (notation de Hill) :
C23H34O5
Numéro CAS:
73573-88-3
Poids moléculaire :
390.51
Beilstein:
1269441
Numéro MDL:
MFCD05662341
Code UNSPSC :
12352200
ID de substance PubChem :
24278540
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Forme

powder or crystals

Couleur

white to light yellow

Pf

151 °C

Solubilité

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

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

enzyme | inhibits

Auteur

Daiichi-Sankyo

Température de stockage

2-8°C

Chaîne 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

Clé InChI

AJLFOPYRIVGYMJ-INTXDZFKSA-N

Informations sur le gène

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

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Catégories apparentées

Description générale

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

Application

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

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

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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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Articles

Dietary Terpenes

Dietary Terpenes

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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