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Merck

M2537

Mevastatin

≥98% (HPLC), 3-hydroxy 3-methyl glutaryl coenzyme(A) reductase (HMG-CoA reductase) inhibitor, powder or crystals

Synonyme(s) :

Compactin, ML-236B

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A propos de cet article

Formule empirique (notation de Hill) :
C23H34O5
Numéro CAS:
73573-88-3
Poids moléculaire :
390.51
NACRES:
NA.77
PubChem Substance ID:
24278540
UNSPSC Code:
12352200
MDL number:
MFCD05662341
Beilstein/REAXYS Number:
1269441
Assay:
≥98% (HPLC)
Form:
powder or crystals
Quality level:
200

Principaux documents

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Nom du produit

Mevastatin, ≥98% (HPLC), powder or crystals

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

SMILES string

[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 key

AJLFOPYRIVGYMJ-INTXDZFKSA-N

assay

≥98% (HPLC)

form

powder or crystals

color

white to light yellow

mp

151 °C

solubility

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

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

originator

Daiichi-Sankyo

storage temp.

2-8°C

Quality Level

200

Gene Information

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

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Catégories apparentées

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

Biochem/physiol Actions

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.

Features and Benefits

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

General description

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000439793
0000439793
0000189655
0000144969
0000246558

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Consulter la Bibliothèque de documents

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
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
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
Uyen T T Nguyen et al.
Nature chemical biology, 5(4), 227-235 (2009-02-17)
Protein prenylation is a widespread phenomenon in eukaryotic cells that affects many important signaling molecules. We describe the structure-guided design of engineered protein prenyltransferases and their universal synthetic substrate, biotin-geranylpyrophosphate. These new tools allowed us to detect femtomolar amounts of
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Product Information Sheet - M2537

Product Information Sheet

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