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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
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
Mahesh Saqcena et al.
Cell cycle (Georgetown, Tex.), 14(14), 2285-2292 (2015-05-07)
Mutations in genes encoding regulators of mTOR, the mammalian target of rapamycin, commonly provide survival signals in cancer cells. Rapamycin and analogs of rapamycin have been used with limited success in clinical trials to target mTOR-dependent survival signals in a
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