CB-839
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MedKoo CAT#: 206153

CAS#: 1439399-58-2

Description: CB-839 an is orally bioavailable inhibitor of glutaminase, with potential antineoplastic activity. Upon oral administration, CB-839 selectively and irreversibly inhibits glutaminase, a mitochondrial enzyme that is essential for the conversion of the amino acid glutamine into glutamate. By blocking glutamine utilization, proliferation in rapidly growing cells is impaired. Glutamine-dependent tumors rely on the conversion of exogenous glutamine into glutamate and glutamate metabolites to both provide energy and generate building blocks for the production of macromolecules, which are needed for cellular growth and survival.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 750
1g
USD 3450
Size
Price

25mg
USD 250
200mg
USD 1250
2g
USD 5950
Size
Price

50mg
USD 450
500mg
USD 1950
5g
Ask price

CB-839, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 2g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206153
Name: CB-839
CAS#: 1439399-58-2
Chemical Formula: C26H24F3N7O3S
Exact Mass: 571.16134
Molecular Weight: 571.57
Elemental Analysis: C, 54.63; H, 4.23; F, 9.97; N, 17.15; O, 8.40; S, 5.61


Synonym: CB839; CB-839; CB 839.

IUPAC/Chemical Name: 2-(pyridin-2-yl)-N-(5-(4-(6-(2-(3-(trifluoromethoxy)phenyl)acetamido)pyridazin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)acetamide

InChi Key: PRAAPINBUWJLGA-UHFFFAOYSA-N

InChi Code: InChI=1S/C26H24F3N7O3S/c27-26(28,29)39-20-9-5-6-17(14-20)15-22(37)31-21-12-11-18(33-34-21)7-1-2-10-24-35-36-25(40-24)32-23(38)16-19-8-3-4-13-30-19/h3-6,8-9,11-14H,1-2,7,10,15-16H2,(H,31,34,37)(H,32,36,38)

SMILES Code: O=C(NC1=CC=C(CCCCC2=NN=C(NC(CC3=NC=CC=C3)=O)S2)N=N1)CC4=CC(OC(F)(F)F)=CC=C4


Technical Data

Appearance:
Solid powder

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

Safety Data Sheet (MSDS):

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, not in water

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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Gross MI, Demo SD, Dennison JB, Chen L, Chernov-Rogan T, Goyal B, Janes JR, Laidig GJ, Lewis ER, Li J, Mackinnon AL, Parlati F, Rodriguez ML, Shwonek PJ, Sjogren EB, Stanton TF, Wang T, Yang J, Zhao F, Bennett MK. Antitumor activity of the glutaminase inhibitor CB-839 in triple-negative breast cancer. Mol Cancer Ther. 2014 Apr;13(4):890-901. doi: 10.1158/1535-7163.MCT-13-0870. PubMed PMID: 24523301.

2: McDermott LA, Iyer P, Vernetti L, Rimer S, Sun J, Boby M, Yang T, Fioravanti M, O'Neill J, Wang L, Drakes D, Katt W, Huang Q, Cerione R. Design and evaluation of novel glutaminase inhibitors. Bioorg Med Chem. 2016 Apr 15;24(8):1819-39. doi: 10.1016/j.bmc.2016.03.009. PubMed PMID: 26988803.

3: Momcilovic M, Bailey ST, Lee JT, Fishbein MC, Magyar C, Braas D, Graeber T, Jackson NJ, Czernin J, Emberley E, Gross M, Janes J, Mackinnon A, Pan A, Rodriguez M, Works M, Zhang W, Parlati F, Demo S, Garon E, Krysan K, Walser TC, Dubinett SM, Sadeghi S, Christofk HR, Shackelford DB. Targeted Inhibition of EGFR and Glutaminase Induces Metabolic Crisis in EGFR Mutant Lung Cancer. Cell Rep. 2017 Jan 17;18(3):601-610. doi: 10.1016/j.celrep.2016.12.061. PubMed PMID: 28099841; PubMed Central PMCID: PMC5260616.

4: Ramachandran S, Pan CQ, Zimmermann SC, Duvall B, Tsukamoto T, Low BC, Sivaraman J. Structural basis for exploring the allosteric inhibition of human kidney type glutaminase. Oncotarget. 2016 Sep 6;7(36):57943-57954. doi: 10.18632/oncotarget.10791. PubMed PMID: 27462863.

5: Jacque N, Ronchetti AM, Larrue C, Meunier G, Birsen R, Willems L, Saland E, Decroocq J, Maciel TT, Lambert M, Poulain L, Hospital MA, Sujobert P, Joseph L, Chapuis N, Lacombe C, Moura IC, Demo S, Sarry JE, Recher C, Mayeux P, Tamburini J, Bouscary D. Targeting glutaminolysis has antileukemic activity in acute myeloid leukemia and synergizes with BCL-2 inhibition. Blood. 2015 Sep 10;126(11):1346-56. doi: 10.1182/blood-2015-01-621870. PubMed PMID: 26186940; PubMed Central PMCID: PMC4608389.

6: Matre P, Velez J, Jacamo R, Qi Y, Su X, Cai T, Chan SM, Lodi A, Sweeney SR, Ma H, Davis RE, Baran N, Haferlach T, Su X, Flores ER, Gonzalez D, Konoplev S, Samudio I, DiNardo C, Majeti R, Schimmer AD, Li W, Wang T, Tiziani S, Konopleva M. Inhibiting glutaminase in acute myeloid leukemia: metabolic dependency of selected AML subtypes. Oncotarget. 2016 Nov 29;7(48):79722-79735. doi: 10.18632/oncotarget.12944. PubMed PMID: 27806325.

7: Zimmermann SC, Wolf EF, Luu A, Thomas AG, Stathis M, Poore B, Nguyen C, Le A, Rojas C, Slusher BS, Tsukamoto T. Allosteric Glutaminase Inhibitors Based on a 1,4-Di(5-amino-1,3,4-thiadiazol-2-yl)butane Scaffold. ACS Med Chem Lett. 2016 Mar 13;7(5):520-4. doi: 10.1021/acsmedchemlett.6b00060. PubMed PMID: 27200176; PubMed Central PMCID: PMC4868099.

8: Katt WP, Lukey MJ, Cerione RA. A tale of two glutaminases: homologous enzymes with distinct roles in tumorigenesis. Future Med Chem. 2017 Jan;9(2):223-243. doi: 10.4155/fmc-2016-0190. PubMed PMID: 28111979.

9: Lorendeau D, Rinaldi G, Boon R, Spincemaille P, Metzger K, Jäger C, Christen S, Dong X, Kuenen S, Voordeckers K, Verstreken P, Cassiman D, Vermeersch P, Verfaillie C, Hiller K, Fendt SM. Dual loss of succinate dehydrogenase (SDH) and complex I activity is necessary to recapitulate the metabolic phenotype of SDH mutant tumors. Metab Eng. 2016 Nov 12. pii: S1096-7176(16)30217-8. doi: 10.1016/j.ymben.2016.11.005. [Epub ahead of print] PubMed PMID: 27847310.

10: Elgogary A, Xu Q, Poore B, Alt J, Zimmermann SC, Zhao L, Fu J, Chen B, Xia S, Liu Y, Neisser M, Nguyen C, Lee R, Park JK, Reyes J, Hartung T, Rojas C, Rais R, Tsukamoto T, Semenza GL, Hanes J, Slusher BS, Le A. Combination therapy with BPTES nanoparticles and metformin targets the metabolic heterogeneity of pancreatic cancer. Proc Natl Acad Sci U S A. 2016 Sep 6;113(36):E5328-36. doi: 10.1073/pnas.1611406113. PubMed PMID: 27559084; PubMed Central PMCID: PMC5018752.

11: Guo L, Zhou B, Liu Z, Xu Y, Lu H, Xia M, Guo E, Shan W, Chen G, Wang C. Blockage of glutaminolysis enhances the sensitivity of ovarian cancer cells to PI3K/mTOR inhibition involvement of STAT3 signaling. Tumour Biol. 2016 Aug;37(8):11007-15. doi: 10.1007/s13277-016-4984-3. PubMed PMID: 26894601.

12: Chakrabarti G, Moore ZR, Luo X, Ilcheva M, Ali A, Padanad M, Zhou Y, Xie Y, Burma S, Scaglioni PP, Cantley LC, DeBerardinis RJ, Kimmelman AC, Lyssiotis CA, Boothman DA. Targeting glutamine metabolism sensitizes pancreatic cancer to PARP-driven metabolic catastrophe induced by ß-lapachone. Cancer Metab. 2015 Oct 12;3:12. doi: 10.1186/s40170-015-0137-1. PubMed PMID: 26462257; PubMed Central PMCID: PMC4601138.