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M2147

Sigma-Aldrich

Mevinolin from Aspergillus sp.

≥98% (HPLC)

Sinónimos:

Monacolin K

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About This Item

Fórmula empírica (notación de Hill):
C24H36O5
Número de CAS:
75330-75-5
Peso molecular:
404.54
Número MDL:
MFCD00072164
Código UNSPSC:
12161501
ID de la sustancia en PubChem:
24896706
NACRES:
NA.77

Nivel de calidad

300

Análisis

≥98% (HPLC)

formulario

crystalline powder

mp

175.4 °C

solubilidad

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

emisor

Abbott

temp. de almacenamiento

2-8°C

cadena SMILES

[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

Clave InChI

PCZOHLXUXFIOCF-BXMDZJJMSA-N

Información sobre el gen

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

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Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Pictogramas

Health hazard
GHS08

Palabra de señalización

Warning

Frases de peligro

H351,H361f

Clasificaciones de peligro

Carc. 2 - Repr. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sarah Ouahoud et al.
British journal of cancer, 124(12), 1978-1987 (2021-03-21)
Epidemiological studies and meta-analyses show an association between statin use and a reduced incidence of colorectal cancer (CRC). We have shown that statins act on CRC through bone morphogenetic protein (BMP) signalling, but the exact cellular targets and underlying mechanism
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
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
Ryohei Miyata et al.
Toxicology and applied pharmacology, 272(1), 1-11 (2013-06-13)
Exposure to ambient air particulate matter (particles less than 10μm or PM10) has been shown to be an independent risk factor for the development and progression of atherosclerosis. The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors (statins) have well-established anti-inflammatory properties. The
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