SML2356
A939572
≥98% (HPLC)
Synonym(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
Empirical Formula (Hill Notation):
C20H22ClN3O3
CAS Number:
Molecular Weight:
387.86
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
SMILES string
Clc1c(cccc1)OC2CCN(CC2)C(=O)Nc3cc(ccc3)C(=O)NC
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)
InChI key
DPYTYQFYDLYWHZ-UHFFFAOYSA-N
Biochem/physiol Actions
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).
Orally available, potent and selective stearoyl-CoA-desaturase 1 (SCD1) inhibitor.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_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.
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
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