Key Documents

View All Documentation

S5944

S-15176 difumarate salt

Name: S-15176 difumarate salt
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

N-[(3,5-Di-tert-butyl-4-hydroxy-1-thiophenyl)]-3-propyl-N′-(2,3,4-trimethoxybenzyl)piperazine difumarate salt

Select a Size

Change View

About This Item

Linear Formula:

C₃₁H₄₈N₂O₄S · 2 C₄H₄O₄

CAS Number:

148913-55-7

Molecular Weight:

776.93

NACRES:

NA.77

PubChem Substance ID:

329824557

UNSPSC Code:

12352200

MDL number:

MFCD11046049

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Quality Level

100

assay

≥98% (HPLC)

form

solid

solubility

DMSO: soluble 16 mg/mL, H₂O: insoluble

storage temp.

2-8°C

SMILES string

OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.COc1ccc(CN2CCN(CCCSc3cc(c(O)c(c3)C(C)(C)C)C(C)(C)C)CC2)c(OC)c1OC

InChI

1S/C31H48N2O4S.2C4H4O4/c1-30(2,3)24-19-23(20-25(27(24)34)31(4,5)6)38-18-10-13-32-14-16-33(17-15-32)21-22-11-12-26(35-7)29(37-9)28(22)36-8;2*5-3(6)1-2-4(7)8/h11-12,19-20,34H,10,13-18,21H2,1-9H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+

InChI key

ANXPOPNCJIJXJW-LVEZLNDCSA-N

Related Categories

Bioactive Small Molecule Inhibitors

Application

The protonophoric activity of S-15176 difumarate salt was studied in mitochondria isolated from livers of Wistar rats.⁵

Biochem/physiol Actions

Antioxidant and anti-ischemic agent. Also inhibits mitochondrial permeability transition, prevents the early step in apoptosis by preventing collapse of the electrochemical gradient across the mitochondrial membrane. IC₅₀ for in vitro lipid peroxidation is 0.3 μM. IC₅₀ for carnitine palmitoyltransferase (CPT-1) in heart homogenate is 16.8 μM. The shift from fatty acid to glucose oxidation may contribute to anti-ischemic effect.

Antioxidant and anti-ischemic agent; inhibits mitochondrial permeability transition, prevents the early step in apoptosis by preventing collapse of the electrochemical gradient across the mitochondrial membrane.

S-15176 suppresses the mitochondrial permeability transition in response to calcium ions and inorganic phosphate and inhibits the release of cytochrome c in response to silver ions. It exhibits weak protonophoric activity.⁵

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

084K4616

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

S-15176 inhibits mitochondrial permeability transition via a mechanism independent of its antioxidant properties.

Aziz Elimadi et al.

European journal of pharmacology, 468(2), 93-101 (2003-05-14)

Mitochondrial Ca(2+) accumulation can induce a sudden increase in the permeability of the inner membrane. This phenomenon is due to the generation of a large nonselective ion channel, termed the permeability transition pore (PTP), which contributes to cellular injury during

S-15176 reduces the hepatic injury in rats subjected to experimental ischemia and reperfusion.

A Settaf et al.

European journal of pharmacology, 406(2), 281-292 (2000-10-06)

The protective effect of N-[(3, 5-di-tertiobutyl-4-hydroxy-1-thiophenyl)]-3-propyl-N'-(2,3, 4-trimethoxybenzyl)piperazine (S-15176) on liver injury induced by warm ischemia-reperfusion was investigated using a rat model. Animals were subjected to 2 h of ischemia followed by different reperfusion times. Hepatocyte integrity was assessed by measuring

S-15176 and its methylated derivative suppress the CsA-insensitive mitochondrial permeability transition and subsequent cytochrome c release induced by silver ion, and show weak protonophoric activity.

Satoshi Kawashima et al.

Molecular and cellular biochemistry, 358(1-2), 45-51 (2011-06-21)

A recent report has described that S-15176 (N-[(3,5-di-tert-butyl-4-hydroxy-1-thiophenyl)]-3-propyl-N'-(2,3,4-trimethoxybenzyl) piperazine), an anti-ischemic agent, inhibits the mitochondrial permeability transition (PT) induced by not only Ca(2+) and inorganic phosphate, but also by tert-butylhydroperoxide or phenylarsine oxide [Morin et al. (Biochem Pharmacol 72:911-918, 2006)].

The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure.

Heinz Rupp et al.

Herz, 27(7), 621-636 (2002-11-20)

Partial fatty acid oxidation inhibitors have raised great interest since they are expected to counteract a dysregulated gene expression of hypertrophied cardiocytes. Some of these compounds have been developed for treating non-insulin-dependent diabetes mellitus and stable angina pectoris. A shift

Inhibition of mitochondrial carnitine palmitoyltransferase-1 by a trimetazidine derivative, S-15176.

M Hamdan et al.

Pharmacological research, 44(2), 99-104 (2001-08-23)

The purpose of this study was to investigate the possible effect of the trimetazidine derivative S-15176 on carnitine palmitoyltransferase1 (CPT-1) activity in rat heart and liver mitochondria. S-15176 was compared with the other antianginal agents amiodarone, perhexiline and trimetazidine, which

Global Trade Item Number

SKU	GTIN
S5944-2MG	04061833274217
S5944-10MG	04061833274200

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service