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SML2356

Sigma-Aldrich

A939572

≥98% (HPLC)

Synonyme(s) :

4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide, 4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-piperidinecarboxamide, A 939572, A939

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About This Item

Formule empirique (notation de Hill):
C20H22ClN3O3
Numéro CAS:
1032229-33-6
Poids moléculaire :
387.86
Numéro MDL:
MFCD10698997
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

InChI

1S/C20H22ClN3O3/c1-22-19(25)14-5-4-6-15(13-14)23-20(26)24-11-9-16(10-12-24)27-18-8-3-2-7-17(18)21/h2-8,13,16H,9-12H2,1H3,(H,22,25)(H,23,26)

Clé InChI

DPYTYQFYDLYWHZ-UHFFFAOYSA-N

Actions biochimiques/physiologiques

A939572 is an orally available piperidine-aryl urea-based small molecule that inhibits stearoyl-CoA desaturase 1 (SCD1) with high potency (IC50 = 37 nM/hSCD1 and <4 nM/mSCD1) with little hERG channel blockade activity (IC50 >100 μM). When administered in ob/ob mice, A939572 effectively reduces desaturation indices in vivo (18:0/18:1n9 ratio from 26.9 to 8.47 in liver; from 15.4 to 7.35 in plasma post 5-day 10 mg/kg bid p.o.). A939572 is a useful tool for probing SCD1-mediated physiological and pathological processes both in cultures (50 nM-10 μM) and in vivo (5-10 mg/kg i.p. or 10 mg/kg p.o. in mice).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Hyeonwoo Kim et al.
Cell reports, 13(3), 495-503 (2015-10-13)
Some cancer cells exhibit elevated levels of free fatty acids (FAs) as well as high levels of β-catenin, a transcriptional co-activator that promotes their growth. Here, we link these two phenomena by showing that unsaturated FAs inhibit degradation of β-catenin.
Mohamed A Lounis et al.
American journal of physiology. Endocrinology and metabolism, 313(6), E710-E720 (2017-08-31)
Stearoyl-CoA desaturase-1 (SCD1) is a key player in lipid metabolism. SCD1 catalyzes the synthesis of monounsaturated fatty acids (MUFA). MUFA are then incorporated into triacylglycerols and phospholipids. Previous studies have shown that Scd1 deficiency in mice induces metabolic changes in
Mohamed A Lounis et al.
Biochimica et biophysica acta, 1861(11), 1662-1670 (2016-08-02)
Stearoyl-CoA desaturase 1 (SCD1) is a delta-9 fatty acid desaturase that catalyzes the synthesis of mono-unsaturated fatty acids (MUFA). SCD1 is a critical control point regulating hepatic lipid synthesis and β-oxidation. Scd1 KO mice are resistant to the development of
Ling Chen et al.
Scientific reports, 6, 19665-19665 (2016-01-28)
Inhibition of stearoyl-CoA desaturase 1 (SCD1) has been found to effectively suppress tumor cell proliferation and induce apoptosis in numerous neoplastic lesions. However, mechanism underlying SCD1-mediated anti-tumor effect has maintained unclear. Herein, we reported endo-lipid messenger ceramides played a critical
Justyna Janikiewicz et al.
Journal of lipid research, 56(10), 1901-1911 (2015-08-22)
Autophagy is indispensable for the proper architecture and flawless functioning of pancreatic β-cells. A growing body of evidence indicates reciprocal communication between autophagic pathways, apoptosis, and intracellular lipids. The way in which elevated levels of free saturated or unsaturated FAs
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