ESI-09 is a novel noncyclic nucleotide EPAC antagonist that is capable of specifically blocking intracellular EPAC-mediated Rap1 activation and Akt phosphorylation, as well as EPAC-mediated insulin secretion in pancreatic β cells. EPAC1 plays an important role in pancreatic cancer cell migration and invasion, and thus represents a potential target for developing novel therapeutic strategies for pancreatic cancer. MedKoo Cat#: 406603 Name: ESI-09 CAS#: 263707-16-0 Chemical Formula: C16H15ClN4O2 Exact Mass: 330.08835 Molecular Weight: 330.77 Elemental Analysis: C, 58.10; H, 4.57; Cl, 10.72; N, 16.94; O, 9.67 Synonym: ESI09; ESI 09; ESI-09. IUPAC/Chemical Name: (E)-2-(5-(tert-butyl)isoxazol-3-yl)-N'-(3-chlorophenyl)-2-oxoacetohydrazonoyl cyanide InChi Key: DXEATJQGQHDURZ-DEDYPNTBSA-N InChi Code: InChI=1S/C16H15ClN4O2/c1-16(2,3)14-8-12(21-23-14)15(22)13(9-18)20-19-11-6-4-5-10(17)7-11/h4-8,19H,1-3H3/b20-13+ SMILES Code: N#C/C(C(C1=NOC(C(C)(C)C)=C1)=O)=N\NC2=CC=CC(Cl)=C2 Technical Data 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, 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: Aslam M, Tanislav C, Troidl C, Schulz R, Hamm C, Gündüz D. cAMP controls the restoration of endothelial barrier function after thrombin-induced hyperpermeability via Rac1 activation. Physiol Rep. 2014 Oct 24;2(10). pii: e12175. doi: 10.14814/phy2.12175. Print 2014 Oct 1. PubMed PMID: 25344477; PubMed Central PMCID: PMC4254100. 2: Mediero A, Perez-Aso M, Cronstein BN. Activation of EPAC1/2 is essential for osteoclast formation by modulating NFκB nuclear translocation and actin cytoskeleton rearrangements. FASEB J. 2014 Nov;28(11):4901-13. doi: 10.1096/fj.14-255703. Epub 2014 Aug 13. PubMed PMID: 25122553; PubMed Central PMCID: PMC4200330. 3: Bacallao K, Monje PV. Opposing roles of PKA and EPAC in the cAMP-dependent regulation of schwann cell proliferation and differentiation [corrected]. PLoS One. 2013 Dec 11;8(12):e82354. doi: 10.1371/journal.pone.0082354. eCollection 2013. Erratum in: PLoS One. 2014;9(1). doi:10.1371/annotation/fa651e8d-ed5a-4937-8d7e-8009b10dcbe0. PubMed PMID: 24349260; PubMed Central PMCID: PMC3859537. 4: Gong B, Shelite T, Mei FC, Ha T, Hu Y, Xu G, Chang Q, Wakamiya M, Ksiazek TG, Boor PJ, Bouyer DH, Popov VL, Chen J, Walker DH, Cheng X. Exchange protein directly activated by cAMP plays a critical role in bacterial invasion during fatal rickettsioses. Proc Natl Acad Sci U S A. 2013 Nov 26;110(48):19615-20. doi: 10.1073/pnas.1314400110. Epub 2013 Nov 11. PubMed PMID: 24218580; PubMed Central PMCID: PMC3845138. 5: Li X, Guo Q, Gao J, Yang J, Zhang W, Liang Y, Wu D, Liu Y, Weng J, Li Q, Zhang Y. The adenylyl cyclase inhibitor MDL-12,330A potentiates insulin secretion via blockade of voltage-dependent K(+) channels in pancreatic beta cells. PLoS One. 2013 Oct 29;8(10):e77934. doi: 10.1371/journal.pone.0077934. eCollection 2013. PubMed PMID: 24205033; PubMed Central PMCID: PMC3812155. 6: Rehmann H. Epac-inhibitors: facts and artefacts. Sci Rep. 2013 Oct 23;3:3032. doi: 10.1038/srep03032. PubMed PMID: 24149987; PubMed Central PMCID: PMC3805970. 7: Chen H, Ding C, Wild C, Liu H, Wang T, White MA, Cheng X, Zhou J. Efficient Synthesis of ESI-09, A Novel Non-cyclic Nucleotide EPAC Antagonist. Tetrahedron Lett. 2013 Mar 20;54(12):1546-1549. PubMed PMID: 23459418; PubMed Central PMCID: PMC3580859. 8: Almahariq M, Tsalkova T, Mei FC, Chen H, Zhou J, Sastry SK, Schwede F, Cheng X. A novel EPAC-specific inhibitor suppresses pancreatic cancer cell migration and invasion. Mol Pharmacol. 2013 Jan;83(1):122-8. doi: 10.1124/mol.112.080689. Epub 2012 Oct 11. PubMed PMID: 23066090; PubMed Central PMCID: PMC3533471.