WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201572
Description: Saridegib, also known as IPI-926, is an orally bioavailable, cyclopamine-derived (for structure comparison see Fig 1) inhibitor of the Hedgehog (Hh) pathway with potential antineoplastic activity. Specifically, Hedgehog pathway inhibitor IPI-926 binds to and inhibits the cell membrane-spanning G-protein coupled receptor SMO, which may result in the suppression of Hh pathway signaling and a decrease in tumor cell proliferation and survival. SMO is activated upon binding of Hh ligand to the cell surface receptor Patched (PTCH); inappropriate activation of Hh signaling and uncontrolled cellular proliferation may be associated with SMO mutations.
MedKoo Cat#: 201572
Chemical Formula: C29H48N2O3S
Exact Mass: 504.33856
Molecular Weight: 504.76802
Elemental Analysis: C, 69.00; H, 9.58; N, 5.55; O, 9.51; S, 6.35
Synonym: IPI 926; IPI-926; IPI926; Saridegib
IUPAC/Chemical Name: N-((2S,3R,3aS,3'R,4a'R,6S,6a'R,6b'S,7aR,12a'S,12b'S)-3,6,11',12b'-tetramethyl-2',3a,3',4,4',4a',5,5',6,6',6a',6b',7,7a,7',8',10',12',12a',12b'-icosahydro-1'H,3H-spiro[furo[3,2-b]pyridine-2,9'-naphtho[2,1-a]azulen]-3'-yl)methanesulfonamide
InChi Key: HZLFFNCLTRVYJG-WWGOJCOQSA-N
InChi Code: InChI=1S/C29H48N2O3S/c1-17-12-26-27(30-16-17)19(3)29(34-26)11-9-22-23-7-6-20-13-21(31-35(5,32)33)8-10-28(20,4)25(23)14-24(22)18(2)15-29/h17,19-23,25-27,30-31H,6-16H2,1-5H3/t17-,19+,20+,21+,22-,23-,25-,26+,27-,28-,29-/m0/s1
SMILES Code: CS(=O)(N[C@H](CC[C@@]12C)C[C@@]1([H])CC[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)=O
Fig 1. Chemical structure comparison between IPI-926 and cyclopamine
IPI-926 is currently developed by Infinity Pharmaceuticals, Inc. Malignant activation of the Hedgehog pathway is implicated in multiple cancer settings and Infinity's development strategy is designed to enable IPI-926 to target a broad range of critical oncology targets - from the tumor cell to the cancer microenvironment. This broadly applicable, targeted approach represents an innovative method for fighting cancer and has potential in treating a range of cancers, including pancreatic cancer, small cell lung cancer, ovarian cancer, bladder cancer, medulloblastoma, basal cell carcinoma, and certain hematological malignancies.
1. Austad, B.; Bahadoor, A.; Belani, J. D.; Janardanannair, S.; Johannes, C. W.; Keaney, G. F.; Lo, C. K.; Wallerstein, S. L. Enzymatic transamination of cyclopamine analogs. WO2011017551A1.