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Merck

M2147

Mevinolin

≥98% (HPLC), HMG-CoA reductase inhibitor, crystalline powder

Synonym(s):

2-Methyl-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester butanoic acid, 6-α-Methylcompactin, Lovastatin, Monacolin K

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About This Item

Empirical Formula (Hill Notation):
C24H36O5
CAS Number:
75330-75-5
Molecular Weight:
404.54
UNSPSC Code:
12161501
PubChem Substance ID:
24896706
NACRES:
NA.77
MDL number:
MFCD00072164

Product Name

Mevinolin from Aspergillus sp., ≥98% (HPLC)

SMILES string

[H][C@]12[C@H](C[C@@H](C)C=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/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

InChI key

PCZOHLXUXFIOCF-BXMDZJJMSA-N

assay

≥98% (HPLC)

form

crystalline powder

mp

175.4 °C

solubility

ethanol: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

originator

Abbott

storage temp.

2-8°C

Quality Level

300

Gene Information

human ... HMGCR(3156)
rat ... Hmgcr(25675)

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Biochem/physiol Actions

Lovastatin is a cholesterol lowering drug and competitive inhibitor of HMG-CoA reductase, a rate limiting enzyme in cholesterol synthesis. Blocks the production of mevalonate, a critical compound in the production of cholesterol and isoprenoids. This product is a substrate of Pgp and CYP3A. It increases cellular resistance to anticancer agents such as doxorubicin and induces apoptosis in myeloma cells. The roles of Pgp and CYP3A, possible connection between drug resistance, regulation of the mevalonate pathway, and iosprenylation of signaling proteins in these observations remain to be resolved. The product induces apoptosis in numerous cancer cell lines perhaps, in part, by inhibiting the isoprenylation of Rho family GTPases. It causes cell cycle arrest in G1 and G2/M phases.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Carc. 2 - Repr. 2

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000520218
0000520218
0000143897
0000143897
0000408043

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N W C J van de Donk et al.
Leukemia, 16(7), 1362-1371 (2002-07-03)
Lovastatin is an irreversible inhibitor of HMG-CoA reductase and blocks the production of mevalonate, a critical compound in the production of cholesterol and isoprenoids. Isoprenylation of target proteins, like the GTP-binding protein Ras, is essential for their membrane localization and
Wen-Bin Zhong et al.
Endocrinology, 144(9), 3852-3859 (2003-08-23)
Lovastatin has been used to treat hypercholesterolemia through blocking the mevalonate biosynthesis pathway. Inhibition of mevalonate synthesis may result in antiproliferation and cell apoptosis. The aim of the present study was to examine the apoptotic effect of lovastatin in human
Kimberly A Hartwell et al.
Nature chemical biology, 9(12), 840-848 (2013-10-29)
Efforts to develop more effective therapies for acute leukemia may benefit from high-throughput screening systems that reflect the complex physiology of the disease, including leukemia stem cells (LSCs) and supportive interactions with the bone marrow microenvironment. The therapeutic targeting of
Hee Yeon Kim et al.
Experimental & molecular medicine, 50(10), 1-12 (2018-10-20)
Glioblastoma is a highly malignant tumor that easily acquires resistance to treatment. The stem-cell-like character (stemness) has been thought to be closely associated with the treatment resistance of glioblastoma cells. In this study, we determined that farnesyl diphosphate synthase (FDPS)
Chia-Hao Chen et al.
International journal of pharmaceutics, 444(1-2), 18-24 (2013-01-29)
Lovastatin, categorized as a class II compound according to the Biopharmaceutics Classification System, is mainly responsible for the blood cholesterol lowering effect of red yeast rice (RYR). The aim of this study was to compare the dissolution rate, physical state
View All Related Papers

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