GDC-0917 (CUDC-427)

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

MedKoo CAT#: 205468

CAS#: 1446182-94-0

Description: CUDC-427, also known as, GDC-0917, is an orally available, monovalent mimetic of second mitochondrial-derived activator of caspases (Smac/DIABLO) and inhibitor of IAPs (Inhibitor of Apoptosis Proteins) with potential antineoplastic activity. Smac mimetic CUDC-427 binds to the Smac binding groove on IAPs, including the direct caspase inhibitor X chromosome-linked IAP (XIAP) and the cellular IAPs 1 and 2. This inhibits the activities of these IAPs and promotes the induction of apoptosis through apoptotic signaling pathways.


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10mg
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25mg
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GDC-0917 is not in stock, but 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

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Theoretical Analysis

MedKoo Cat#: 205468
Name: GDC-0917 (CUDC-427)
CAS#: 1446182-94-0
Chemical Formula: C29H36N6O4S
Exact Mass: 564.25187
Molecular Weight: 564.7
Elemental Analysis: C, 61.68; H, 6.43; N, 14.88; O, 11.33; S, 5.68


Synonym: GDC0917; GDC-0917; GDC 0917; CUDC427; CUDC-427; CUDC 427.

IUPAC/Chemical Name: (S)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)-N-(2-(oxazol-2-yl)-4-phenylthiazol-5-yl)pyrrolidine-2-carboxamide

InChi Key: HSHPBORBOJIXSQ-HARLFGEKSA-N

InChi Code: InChI=1S/C29H36N6O4S/c1-18(30-2)24(36)32-23(20-12-7-4-8-13-20)29(38)35-16-9-14-21(35)25(37)34-27-22(19-10-5-3-6-11-19)33-28(40-27)26-31-15-17-39-26/h3,5-6,10-11,15,17-18,20-21,23,30H,4,7-9,12-14,16H2,1-2H3,(H,32,36)(H,34,37)/t18-,21-,23-/m0/s1

SMILES Code: O=C([C@H]1N(C([C@H](C2CCCCC2)NC([C@@H](NC)C)=O)=O)CCC1)NC3=C(C4=CC=CC=C4)N=C(C5=NC=CO5)S3


Technical Data

Appearance:
white 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:
GDC-0917 free base is soluble in DMSO, not water soluble. GDC-0917 TFA salt is water soluble.

Shelf Life:
>2 years if stored properly

Drug Formulation:
GDC-0917 TFA was used, which is water soluble. GDC-0917 TFA was formulated in PBS.

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

 CUDC-427 is currently developed by Curis, Inc , who licensed from Genentech. CUDC-417 is an orally bioavailable small molecule that triggers tumor cell apoptosis by selectively antagonizing IAP proteins. CUDC-427 was designed to mimic the endogenous IAP antagonist, second mitochondria-derived activator of caspases/direct IAP-binding protein (Smac/DIABLO) that is released into the cytoplasm in response to pro-apoptotic stimuli. CUDC-427 has demonstrated single-agent and combination therapy anti-tumor activity in mouse xenograft tumor models when administered orally, and IND-enabling safety studies have shown it to be well tolerated when dosed daily by oral administration, potentially enabling sustained target inhibition.
 CUDC-427 is currently developed by
, who licensed from Genentech. CUDC-417 is an orally bioavailable small molecule that triggers tumor cell apoptosis by selectively antagonizing IAP proteins. CUDC-427 was designed to mimic the endogenous IAP antagonist, second mitochondria-derived activator of caspases/direct IAP-binding protein (Smac/DIABLO) that is released into the cytoplasm in response to pro-apoptotic stimuli. CUDC-427 has demonstrated single-agent and combination therapy anti-tumor activity in mouse xenograft tumor models when administered orally, and IND-enabling safety studies have shown it to be well tolerated when dosed daily by oral administration, potentially enabling sustained target inhibition.
   
 


References

1: Wong H, Gould SE, Budha N, Darbonne WC, Kadel EE 3rd, La H, Alicke B, Halladay JS, Erickson R, Portera C, Tolcher AW, Infante JR, Mamounas M, Flygare JA, Hop CE, Fairbrother WJ. Learning and Confirming with Preclinical Studies: Modeling and Simulation in the Discovery of GDC-0917, an IAP Antagonist. Drug Metab Dispos. 2013 41:2104-2113.  PubMed PMID: 24041744.