WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 206089
Description: AZD5582 is a potent IAP inhibitor, which is a dimeric compound based on the AVPI motif of Smac. AZD5582 binds potently to the BIR3 domains of cIAP1, cIAP2, and XIAP (IC50 = 15, 21, and 15 nM, respectively). AZD5582 causes cIAP1 degradation and induces apoptosis in the MDA-MB-231 breast cancer cell line at subnanomolar concentrations in vitro. When administered intravenously to MDA-MB-231 xenograft-bearing mice, AZD5582 results in cIAP1 degradation and caspase-3 cleavage within tumor cells and causes substantial tumor regressions following two weekly doses of 3.0 mg/kg. Antiproliferative effects are observed with 14 in only a small subset of the over 200 cancer cell lines examined, consistent with other published IAP inhibitors. As a result of its in vitro and in vivo profile, AZD5582 was nominated as a candidate for clinical development.
MedKoo Cat#: 206089
Chemical Formula: C58H78N8O8
Exact Mass: 1014.59426
Molecular Weight: 1015.29
Elemental Analysis: C, 68.61; H, 7.74; N, 11.04; O, 12.61
Synonym: AZD5582; AZD-5582; AZD 5582.
IUPAC/Chemical Name: (S,S,2S,2′S)-N,N′-((1S,1′S,2R,2′R)-2,2′-(Hexa-2,4-diyne-1,6-diylbis(oxy))bis(2,3-dihydro-1H-indene-2,1-diyl))bis(1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)-pyrrolidine-2-carboxamide).
InChi Key: WLMCRYCCYXHPQF-ZVMUOSSASA-N
InChi Code: InChI=1S/C58H78N8O8/c1-37(59-3)53(67)61-49(39-21-9-7-10-22-39)57(71)65-31-19-29-45(65)55(69)63-51-43-27-15-13-25-41(43)35-47(51)73-33-17-5-6-18-34-74-48-36-42-26-14-16-28-44(42)52(48)64-56(70)46-30-20-32-66(46)58(72)50(40-23-11-8-12-24-40)62-54(68)38(2)60-4/h13-16,25-28,37-40,45-52,59-60H,7-12,19-24,29-36H2,1-4H3,(H,61,67)(H,62,68)(H,63,69)(H,64,70)/t37-,38-,45-,46-,47+,48+,49-,50-,51-,52-/m0/s1
SMILES Code: CN[C@@H](C)C(N[C@@H](C1CCCCC1)C(N2[C@H](C(N[C@H]3C(C=CC=C4)=C4C[C@H]3OCC#CC#CCO[C@@H]5CC6=C(C=CC=C6)[C@@H]5NC([C@H](CCC7)N7C([C@H](C8CCCCC8)NC([C@H](C)NC)=O)=O)=O)=O)CCC2)=O)=O.
1. Edward J. Hennessy, Ammar Adam, Brian M. Aquila, Lillian M. Castriotta, Donald Cook, Maureen Hattersley, Alexander W. Hird, Christopher Huntington, Victor M. Kamhi, Naomi M. Laing, Danyang Li, Terry MacIntyre, Charles A. Omer, Vibha Oza, Troy Patterson, Galina Repik, Michael T. Rooney, Jamal C. Saeh, Li Sha, Melissa M. Vasbinder, Haiyun Wang, and David Whitston. Discovery of a Novel Class of Dimeric Smac Mimetics as Potent IAP Antagonists Resulting in a Clinical Candidate for the Treatment of Cancer (AZD5582). J. Med. Chem. 2013, 56(24), pp 9897Â–9919.