AZD-5582

WARNING: This product is for research use only, not for human or veterinary use.

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.

Price and Availability

AZD-5582,is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 206089Name: AZD-5582CAS#: 1258392-53-8Chemical Formula: C58H78N8O8Exact Mass: 1014.59426Molecular Weight: 1015.29Elemental 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.

Technical Data

Additional Information

References

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, DanyangLi, Terry MacIntyre, Charles A. Omer, Vibha Oza, Troy Patterson, GalinaRepik, Michael T. Rooney, Jamal C. Saeh, Li Sha, Melissa M. Vasbinder,Haiyun Wang, and David Whitston. Discovery of a Novel Class of DimericSmac Mimetics as Potent IAP Antagonists Resulting in a ClinicalCandidate for the Treatment of Cancer (AZD5582). J. Med. Chem. 2013,56(24), pp 9897–9919.