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Merck
CN

S4194

SR 12813

≥98%, solid

别名:

Tetraethyl 2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethenyl-1,1-bisphosphonate

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关于此项目

经验公式（希尔记法）:
C24H42O7P2
化学文摘社编号:
126411-39-0
分子量:
504.53
NACRES:
NA.77
PubChem Substance ID:
329824541
UNSPSC Code:
12352203
MDL number:
MFCD00888473

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产品名称

SR 12813, ≥98%, solid

InChI

1S/C24H42O7P2/c1-11-28-32(26,29-12-2)21(33(27,30-13-3)31-14-4)17-18-15-19(23(5,6)7)22(25)20(16-18)24(8,9)10/h15-17,25H,11-14H2,1-10H3

SMILES string

CCOP(=O)(OCC)C(=C/c1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C)\P(=O)(OCC)OCC

InChI key

YQLJDECYQDRSBI-UHFFFAOYSA-N

biological source

synthetic (organic)

assay

≥98%

form

solid

solubility

DMSO: ≥10 mg/mL
H2O: insoluble

originator

GlaxoSmithKline

Quality Level

100

相关类别

Application

SR-12813 was used as control in pregnane X receptor (PXR) binding assay performed in HepG2 liver carcinoma cells and PXR-activation assay mediated by dehydroepiandrosterone in human hepatocytes.

Biochem/physiol Actions

SR 12813 is a pregnane X receptor (PXR, NR 112) agonist; cholesterol lowering drug; HMGCoA reductase inhibitor.
SR-12813 is a 1,1-bisphosphonate ester that exhibits hypocholesterolemic activity. It decreases the biosynthesis of cholesterol by enhancing the degradation of HMG-CoA reductase.

Features and Benefits

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

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

法规信息

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分析证书(COA)

Lot/Batch Number
0000523404
0000523404
0000350449
0000334077
0000350449

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Zdeněk Dvořák et al.
EMBO molecular medicine, 12(4), e11621-e11621 (2020-03-11)
The human PXR (pregnane X receptor), a master regulator of drug metabolism, has essential roles in intestinal homeostasis and abrogating inflammation. Existing PXR ligands have substantial off-target toxicity. Based on prior work that established microbial (indole) metabolites as PXR ligands
T A Berkhout et al.
The Journal of biological chemistry, 271(24), 14376-14382 (1996-06-14)
SR-12813 (tetra-ethyl 2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethenyl-1, 1-bisphosphonate) lowers plasma cholesterol in five species. In this paper we investigate the underlying mechanism using Hep G2 cells. SR-12813 inhibited incorporation of tritiated water into cholesterol with an IC50 of 1.2 microM but had no effect
Marija Pinne et al.
PloS one, 11(10), e0164642-e0164642 (2016-10-13)
The pregnane X receptor (PXR/SXR, NR1I2) and constitutive androstane receptor (CAR, NR1I3) are nuclear receptors (NRs) involved in the regulation of many genes including cytochrome P450 enzymes (CYPs) and transporters important in metabolism and uptake of both endogenous substrates and
Krisztina Kohalmy et al.
Drug metabolism and disposition: the biological fate of chemicals, 35(9), 1495-1501 (2007-06-27)
Dehydroepiandrosterone (DHEA), the major precursor of androgens and estrogens, has several beneficial effects on the immune system, on memory function, and in modulating the effects of diabetes, obesity, and chemical carcinogenesis. Treatment of rats with DHEA influences expression of cytochrome
Navdar Sever et al.
The Journal of biological chemistry, 279(41), 43136-43147 (2004-07-13)
Insig-1 and Insig-2 are membrane proteins of the endoplasmic reticulum that regulate lipid metabolism by the following two actions: 1) sterol-induced binding to 3-hydroxy-3-methylglutaryl-coenzyme A reductase, an action that leads to ubiquitination and degradation of the enzyme; and 2) sterol-induced
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商品

Cholesterol Biosynthesis Regulation

Cholesterol synthesis regulation by dietary levels, LDL receptors control lipid-rich LDL particle transport in cells.

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