IPI-269609

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

MedKoo CAT#: 205773

CAS#: NONE

Description: IPI-269609 is a novel, orally bioavailable small-molecule Hedgehog inhibitor. IPI-269609 was tested using in vitro and in vivo model systems. In vitro treatment of pancreatic cancer cell lines with IPI-269609 resembled effects observed using cyclopamine (i.e., Gli-responsive reporter knockdown, down-regulation of the Hedgehog target genes Gli1 and Ptch, as well as abrogation of cell migration and colony formation in soft agar). Single-agent IPI-269609 profoundly inhibited systemic metastases in orthotopic xenografts established from human pancreatic cancer cell lines, although Hedgehog blockade had minimal effect on primary tumor volume. The only discernible phenotype observed within the treated primary tumor was a significant reduction in the population of aldehyde dehydrogenase-bright cells, which we have previously identified as a clonogenic tumor-initiating population in pancreatic cancer. Selective ex vivo depletion of aldehyde dehydrogenase-bright cells with IPI-269609 was accompanied by significant reduction in tumor engraftment rates in athymic mice. (source: Mol Cancer Ther. 2008 Sep;7(9):2725-35.)


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IPI-269609 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#: 205773
Name: IPI-269609
CAS#: NONE
Chemical Formula: C28H41NO2
Exact Mass: 423.31373
Molecular Weight: 423.63
Elemental Analysis: C, 79.39; H, 9.76; N, 3.31; O, 7.55


Synonym: IPI269609; IPI 269609; IPI-269609; IPI609; IPI 609; IPI-609

IUPAC/Chemical Name: (2S,3R,3aS,6S,6a'S,6b'S,7aR,12a'S,12b'R)-3,6,11',12b'-tetramethyl-3a,4,5,5',6,6',6a',6b',7,7a,7',8',10',12',12a',12b'-hexadecahydro-1'H,3H-spiro[furo[3,2-b]pyridine-2,9'-naphtho[2,1-a]azulen]-3'(2'H)-one

InChi Key: MQLNLMKPNAHPDZ-LLMUXGIESA-N

InChi Code: InChI=1S/C28H41NO2/c1-16-11-25-26(29-15-16)18(3)28(31-25)10-8-21-22-6-5-19-12-20(30)7-9-27(19,4)24(22)13-23(21)17(2)14-28/h12,16,18,21-22,24-26,29H,5-11,13-15H2,1-4H3/t16-,18+,21-,22-,24-,25+,26-,27-,28-/m0/s1

SMILES Code: O=C(CC[C@@]12C)C=C1CC[C@]3([H])[C@]2([H])CC4=C(C)C[C@@](O5)(CC[C@@]34[H])[C@H](C)[C@@]6([H])[C@@]5([H])C[C@H](C)CN6


Technical Data

Appearance:
Solid powder

Purity:
>98%

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:
>5 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: Katoh Y, Katoh M. Hedgehog target genes: mechanisms of carcinogenesis induced by aberrant hedgehog signaling activation. Curr Mol Med. 2009 Sep;9(7):873-86. Review. PubMed PMID: 19860666.

2: Tremblay MR, Lescarbeau A, Grogan MJ, Tan E, Lin G, Austad BC, Yu LC, Behnke ML, Nair SJ, Hagel M, White K, Conley J, Manna JD, Alvarez-Diez TM, Hoyt J, Woodward CN, Sydor JR, Pink M, MacDougall J, Campbell MJ, Cushing J, Ferguson J, Curtis MS, McGovern K, Read MA, Palombella VJ, Adams J, Castro AC. Discovery of a potent and orally active hedgehog pathway antagonist (IPI-926). J Med Chem. 2009 Jul 23;52(14):4400-18. PubMed PMID: 19522463.

3: Feldmann G, Fendrich V, McGovern K, Bedja D, Bisht S, Alvarez H, Koorstra JB, Habbe N, Karikari C, Mullendore M, Gabrielson KL, Sharma R, Matsui W, Maitra A. An orally bioavailable small-molecule inhibitor of Hedgehog signaling inhibits tumor initiation and metastasis in pancreatic cancer. Mol Cancer Ther. 2008 Sep;7(9):2725-35. PubMed PMID: 18790753; PubMed Central PMCID: PMC2605523.