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M2537

Mevastatin

Name: Mevastatin
Brand: SIGMA

≥98% (HPLC), powder or crystals

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Synonym(s):

Compactin, ML-236B

Empirical Formula (Hill Notation):

C₂₃H₃₄O₅

CAS Number:

73573-88-3

Molecular Weight:

390.51

Beilstein:

1269441

MDL number:

MFCD05662341

PubChem Substance ID:

24278540

NACRES:

NA.77

Quality Level

200

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

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

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

InChI key

AJLFOPYRIVGYMJ-INTXDZFKSA-N

Gene Information

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

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General description

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

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Compactin suppresses bone resorption by inhibiting the fusion of prefusion osteoclasts and disrupting the actin ring in osteoclasts.

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

Nitrogen-containing bisphosphonates inhibit the mevalonate pathway and prevent post-translational prenylation of GTP-binding proteins, including Ras.

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

Compactin-a review.

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

The bisphosphonate incadronate (YM175) causes apoptosis of human myeloma cells in vitro by inhibiting the mevalonate pathway.

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

The chaperone protein SmgGDS interacts with small GTPases entering the prenylation pathway by recognizing the last amino acid in the CAAX motif.

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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