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M2147

Sigma-Aldrich

Mevinolin from Aspergillus sp.

≥98% (HPLC)

Synonim(y):

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

Wzór empiryczny (zapis Hilla):
C24H36O5
Numer CAS:
75330-75-5
Masa cząsteczkowa:
404.54
Numer MDL:
MFCD00072164
Kod UNSPSC:
12161501
Identyfikator substancji w PubChem:
24896706
NACRES:
NA.77

Poziom jakości

300

Próba

≥98% (HPLC)

Formularz

crystalline powder

mp

175.4 °C

rozpuszczalność

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

inicjator

Abbott

temp. przechowywania

2-8°C

ciąg 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

Klucz InChI

PCZOHLXUXFIOCF-BXMDZJJMSA-N

informacje o genach

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

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Działania biochem./fizjol.

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.

Cechy i korzyści

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.
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Piktogramy

Health hazard
GHS08

Hasło ostrzegawcze

Warning

Zwroty wskazujące rodzaj zagrożenia

H351,H361f

Zwroty wskazujące środki ostrożności

P201 - P202 - P280 - P308 + P313 - P405 - P501

Klasyfikacja zagrożeń

Carc. 2 - Repr. 2

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

Eyeshields, Gloves, type N95 (US)

Wybierz jedną z najnowszych wersji:

Certyfikaty analizy (CoA)

Lot/Batch Number
089M4072V
14181009
068M4153V
14171214
057M4007V

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

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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Produkty

Dietary Terpenes

Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. LDL receptors regulate the cellular transport of lipid rich low density lipoprotein (LDL) particles.

Antilipemic Agents

Randomized controlled clinical studies have suggested 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors (statins) are effective in both primary and secondary prevention of cardiovascular disease (CVD) events.

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