A939572
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MedKoo CAT#: 526965

CAS#: 1032229-33-6

Description: A939572 is is a potent and orally bioavailable inhibitor of stearoyl-CoA desaturase1 (SCD1) with IC50 value of 37nM. Stearoyl-CoA desaturase 1 is a novel molecular therapeutic target for clear cell renal cell carcinoma.


Chemical Structure

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A939572
CAS# 1032229-33-6

Theoretical Analysis

MedKoo Cat#: 526965
Name: A939572
CAS#: 1032229-33-6
Chemical Formula: C20H22ClN3O3
Exact Mass: 387.135
Molecular Weight: 387.864
Elemental Analysis: C, 61.93; H, 5.72; Cl, 9.14; N, 10.83; O, 12.37

Price and Availability

Size Price Availability Quantity
5.0mg USD 250.0 2 Weeks
10.0mg USD 450.0 2 Weeks
50.0mg USD 950.0 2 Weeks
500.0mg USD 3650.0 2 Weeks
1.0g USD 4950.0 2 Weeks
2.0g USD 7950.0 2 Weeks
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Synonym: A939572; A-939572; A 939572; SCD1 Inhibitor; Stearoyl-CoA Desaturase 1 Inhibitor;

IUPAC/Chemical Name: 4-(2-chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-piperidinecarboxamide

InChi Key: DPYTYQFYDLYWHZ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(N1CCC(OC2=CC=CC=C2Cl)CC1)NC3=CC=CC(C(NC)=O)=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: A939572 is a stearoyl-CoA desaturase1 (SCD1) inhibitor with IC50 values of <4 nM and 37 nM for mSCD1 and hSCD1, respectively.
In vitro activity: To test whether SCD activity is necessary for PDAC, this study analyzed the role of SCD1 in human PDAC cell line, PANC-1. PANC-1 reduced its proliferation by treatment with A939572 (10–100 μM) for 2 days (Fig. 5A). However, this study did not observe induction of cytotoxicity by A939572 (Fig. 5B). Western blot analysis showed induction of phosphorylation and expression of eIF2α by 5 and 20 μM of A939572 in PANC-1 (Fig. 5C). However, A939572 treatment did not induce the cleavage of Caspase-3 (Fig. 5C) or PARP (data not shown), indicating that the suppression of SCD1 induces the UPR but does not induce cell death in PANC-1. Reference: Pancreas. 2021 Feb 1;50(2):219-226. https://pubmed.ncbi.nlm.nih.gov/33565799/
In vivo activity: To further investigate the correlation between MUFAs and FAAH activity in the liver, HFD-fed WT, CB1R−/−, and htgCB1R−/− mice were treated with vehicle or 5 mg/kg/d of the SCD1 inhibitor A939572 for 12 wk. A939572 treatment effectively inhibited SCD1 activity in the liver and reversed the HFD-induced decrease in hepatic FAAH activity and the associated increase in hepatic AEA levels in WT and htgCB1R−/− mice, but not in the CB1R−/− mice (Fig. 5). In WT and htgCB1R−/− mice, but not in CB1R−/− mice, the SCD1 inhibitor also normalized plasma insulin levels as well as liver triglyceride content and improved glucose tolerance and insulin sensitivity (Fig. 5). These results clearly support the link between the hepatic endocannabinoid/CB1R system and SCD1 activity. Reference: Proc Natl Acad Sci U S A. 2013 Nov 19; 110(47): 18832–18837. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3839776/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 46.95 121.05
DMF 1.0 2.58
DMF:PBS (pH 7.2) (1:1) 0.5 1.29
Ethanol 2.75 7.09

Preparing Stock Solutions

The following data is based on the product molecular weight 387.864 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Skrypek K, Balog S, Eriguchi Y, Asahina K. Inhibition of Stearoyl-CoA Desaturase Induces the Unfolded Protein Response in Pancreatic Tumors and Suppresses Their Growth. Pancreas. 2021 Feb 1;50(2):219-226. doi: 10.1097/MPA.0000000000001737. PMID: 33565799; PMCID: PMC7880535. 2. Lucarelli G, Ferro M, Loizzo D, Bianchi C, Terracciano D, Cantiello F, Bell LN, Battaglia S, Porta C, Gernone A, Perego RA, Maiorano E, Cobelli O, Castellano G, Vincenti L, Ditonno P, Battaglia M. Integration of Lipidomics and Transcriptomics Reveals Reprogramming of the Lipid Metabolism and Composition in Clear Cell Renal Cell Carcinoma. Metabolites. 2020 Dec 13;10(12):509. doi: 10.3390/metabo10120509. PMID: 33322148; PMCID: PMC7763669. 3. Liu J, Cinar R, Xiong K, Godlewski G, Jourdan T, Lin Y, Ntambi JM, Kunos G. Monounsaturated fatty acids generated via stearoyl CoA desaturase-1 are endogenous inhibitors of fatty acid amide hydrolase. Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):18832-7. doi: 10.1073/pnas.1309469110. Epub 2013 Nov 4. PMID: 24191036; PMCID: PMC3839776. 4. Paton CM, Ntambi JM. Loss of stearoyl-CoA desaturase activity leads to free cholesterol synthesis through increased Xbp-1 splicing. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E1066-75. doi: 10.1152/ajpendo.00388.2010. Epub 2010 Oct 5. PMID: 20923962; PMCID: PMC3006250.
In vitro protocol: 1. Skrypek K, Balog S, Eriguchi Y, Asahina K. Inhibition of Stearoyl-CoA Desaturase Induces the Unfolded Protein Response in Pancreatic Tumors and Suppresses Their Growth. Pancreas. 2021 Feb 1;50(2):219-226. doi: 10.1097/MPA.0000000000001737. PMID: 33565799; PMCID: PMC7880535. 2. Lucarelli G, Ferro M, Loizzo D, Bianchi C, Terracciano D, Cantiello F, Bell LN, Battaglia S, Porta C, Gernone A, Perego RA, Maiorano E, Cobelli O, Castellano G, Vincenti L, Ditonno P, Battaglia M. Integration of Lipidomics and Transcriptomics Reveals Reprogramming of the Lipid Metabolism and Composition in Clear Cell Renal Cell Carcinoma. Metabolites. 2020 Dec 13;10(12):509. doi: 10.3390/metabo10120509. PMID: 33322148; PMCID: PMC7763669.
In vivo protocol: 1. Liu J, Cinar R, Xiong K, Godlewski G, Jourdan T, Lin Y, Ntambi JM, Kunos G. Monounsaturated fatty acids generated via stearoyl CoA desaturase-1 are endogenous inhibitors of fatty acid amide hydrolase. Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):18832-7. doi: 10.1073/pnas.1309469110. Epub 2013 Nov 4. PMID: 24191036; PMCID: PMC3839776. 2. Paton CM, Ntambi JM. Loss of stearoyl-CoA desaturase activity leads to free cholesterol synthesis through increased Xbp-1 splicing. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E1066-75. doi: 10.1152/ajpendo.00388.2010. Epub 2010 Oct 5. PMID: 20923962; PMCID: PMC3006250.

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1: Bednarski T, Olichwier A, Opasinska A, Pyrkowska A, Gan AM, Ntambi JM, Dobrzyn P. Stearoyl-CoA desaturase 1 deficiency reduces lipid accumulation in the heart by activating lipolysis independently of peroxisome proliferator-activated receptor α. Biochim Biophys Acta. 2016 Oct 15;1861(12 Pt A):2029-2037. doi: 10.1016/j.bbalip.2016.10.005. [Epub ahead of print] PubMed PMID: 27751891.

2: Liu J, Cinar R, Xiong K, Godlewski G, Jourdan T, Lin Y, Ntambi JM, Kunos G. Monounsaturated fatty acids generated via stearoyl CoA desaturase-1 are endogenous inhibitors of fatty acid amide hydrolase. Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):18832-7. doi: 10.1073/pnas.1309469110. PubMed PMID: 24191036; PubMed Central PMCID: PMC3839776.

3: von Roemeling CA, Marlow LA, Wei JJ, Cooper SJ, Caulfield TR, Wu K, Tan WW, Tun HW, Copland JA. Stearoyl-CoA desaturase 1 is a novel molecular therapeutic target for clear cell renal cell carcinoma. Clin Cancer Res. 2013 May 1;19(9):2368-80. doi: 10.1158/1078-0432.CCR-12-3249. PubMed PMID: 23633458; PubMed Central PMCID: PMC3644999.

4: Paton CM, Ntambi JM. Loss of stearoyl-CoA desaturase activity leads to free cholesterol synthesis through increased Xbp-1 splicing. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E1066-75. doi: 10.1152/ajpendo.00388.2010. PubMed PMID: 20923962; PubMed Central PMCID: PMC3006250.

A939572

5.0mg / USD 250.0