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S5944

Sigma-Aldrich

S-15176 difumarate salt

≥98% (HPLC), solid

Synonim(y):

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

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About This Item

Wzór liniowy:
C31H48N2O4S · 2 C4H4O4
Numer CAS:
148913-55-7
Masa cząsteczkowa:
776.93
Numer MDL:
MFCD11046049
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
329824557
NACRES:
NA.77

Próba

≥98% (HPLC)

Postać

solid

rozpuszczalność

DMSO: soluble 16 mg/mL
H2O: insoluble

temp. przechowywania

2-8°C

ciąg SMILES

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+

Klucz InChI

ANXPOPNCJIJXJW-LVEZLNDCSA-N

Zastosowanie

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

Działania biochem./fizjol.

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.
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

Piktogramy

Exclamation mark
GHS07

Hasło ostrzegawcze

Warning

Zwroty wskazujące rodzaj zagrożenia

H315,H319,H335

Zwroty wskazujące środki ostrożności

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

Klasyfikacja zagrożeń

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

Organy docelowe

Respiratory system

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

dust mask type N95 (US), Eyeshields, Gloves

Certyfikaty analizy (CoA)

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Odwiedź Bibliotekę dokumentów

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)].
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
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
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
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

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