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Merck
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Dokumente

M2147

Sigma-Aldrich

Mevinolin from Aspergillus sp.

≥98% (HPLC)

Synonym(e):

Monacolin K

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About This Item

Empirische Formel (Hill-System):
C24H36O5
CAS-Nummer:
75330-75-5
Molekulargewicht:
404.54
MDL-Nummer:
MFCD00072164
UNSPSC-Code:
12161501
PubChem Substanz-ID:
24896706
NACRES:
NA.77

Qualitätsniveau

300

Assay

≥98% (HPLC)

Form

crystalline powder

mp (Schmelzpunkt)

175.4 °C

Löslichkeit

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

Ersteller

Abbott

Lagertemp.

2-8°C

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

InChIKey

PCZOHLXUXFIOCF-BXMDZJJMSA-N

Angaben zum Gen

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

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Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Health hazard
GHS08

Signalwort

Warning

H-Sätze

H351,H361f

Gefahreneinstufungen

Carc. 2 - Repr. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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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
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
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
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
Yong-Seok Lee et al.
Nature neuroscience, 17(12), 1736-1743 (2014-11-11)
In Noonan syndrome (NS) 30-50% of subjects show cognitive deficits of unknown etiology and with no known treatment. Here, we report that knock-in mice expressing either of two NS-associated mutations in Ptpn11, which encodes the nonreceptor protein tyrosine phosphatase Shp2
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