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安全信息

S4194

Sigma-Aldrich

SR 12813

≥98%, solid

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别名:
Tetraethyl 2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethenyl-1,1-bisphosphonate
经验公式（希尔记法）:
C24H42O7P2
CAS号:
126411-39-0
分子量:
504.53
MDL编号:
MFCD00888473
UNSPSC代码:
12352203
PubChem化学物质编号:
329824541
NACRES:
NA.77

生物来源

synthetic (organic)

质量水平

100

检测方案

≥98%

形式

solid

溶解性

DMSO: ≥10 mg/mL
H2O: insoluble

创始人

GlaxoSmithKline

SMILES字符串

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

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

InChI key

YQLJDECYQDRSBI-UHFFFAOYSA-N

应用

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.

生化/生理作用

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.
SR 12813 is a pregnane X receptor (PXR, NR 112) agonist; cholesterol lowering drug; HMGCoA reductase inhibitor.

特点和优势

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.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

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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
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
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
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
Wenwei Lin et al.
The Journal of biological chemistry, 283(45), 30650-30657 (2008-09-12)
The human pregnane X receptor (hPXR) regulates the expression of critical drug metabolism enzymes. One of such enzymes, cytochrome P450 3A4 (CYP3A4), plays critical roles in drug metabolism in hepatocytes that are either quiescent or passing through the cell cycle.

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