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SML2356

Sigma-Aldrich

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:
1032229-33-6
Molecular Weight:
387.86
MDL number:
MFCD10698997
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

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)

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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Keane K Y Lai et al.
Gastroenterology, 152(6), 1477-1491 (2017-02-02)
Stearoyl-CoA desaturase (SCD) synthesizes monounsaturated fatty acids (MUFAs) and has been associated with the development of metabolic syndrome, tumorigenesis, and stem cell characteristics. We investigated whether and how SCD promotes liver fibrosis and tumor development in mice. Rodent primary hepatic
Uri Ben-David et al.
Cell stem cell, 12(2), 167-179 (2013-01-16)
The use of human pluripotent stem cells (hPSCs) in cell therapy is hindered by the tumorigenic risk from residual undifferentiated cells. Here we performed a high-throughput screen of over 52,000 small molecules and identified 15 pluripotent cell-specific inhibitors (PluriSIns), nine
Jingwei Zhang et al.
Adipocyte, 10(1), 646-657 (2021-11-19)
Obesity and associated complications are becoming a pandemic. Inhibiting adipogenesis is an important intervention for the treatment of obesity. Despite intensive investigations, numerous mechanistic aspects of adipogenesis remain unclear, and many potential therapeutic targets have yet to be discovered. Transcriptomics
Urvashi V Roongta et al.
Molecular cancer research : MCR, 9(11), 1551-1561 (2011-09-29)
Emerging literature suggests that metabolic pathways play an important role in the maintenance and progression of human cancers. In particular, recent studies have implicated lipid biosynthesis and desaturation as a requirement for tumor cell survival. In the studies reported here
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
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