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S4194

Sigma-Aldrich

SR 12813

≥98%, solid

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C24H42O7P2
Numero CAS:
126411-39-0
Peso molecolare:
504.53
Numero MDL:
MFCD00888473
Codice UNSPSC:
12352203
ID PubChem:
329824541
NACRES:
NA.77

Origine biologica

synthetic (organic)

Livello qualitativo

100

Saggio

≥98%

Forma fisica

solid

Solubilità

DMSO: ≥10 mg/mL
H2O: insoluble

Ideatore

GlaxoSmithKline

Stringa SMILE

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
YQLJDECYQDRSBI-UHFFFAOYSA-N

Applicazioni

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.

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Mevinolina ≥98% (HPLC)

Sigma-Aldrich

M2147

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Alendronate sodium trihydrate ≥97% (NMR), powder

Sigma-Aldrich

A4978

Alendronate sodium trihydrate

Zoledronic acid monohydrate ≥98% (HPLC)

Sigma-Aldrich

SML0223

Zoledronic acid monohydrate

Rifampicin ≥95% (HPLC), powder or crystals

Sigma-Aldrich

R3501

Rifampicin

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
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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