Saridegib

Saridegib
Names
IUPAC name
N-[(5βH)-5,6-Dihydro-17,23β-epoxy-16a-homoveratraman-3α-yl]methanesulfonamide
Systematic IUPAC name
N-[(2S,3R,3′R,3aS,4′aR,6S,6′aR,6′bS,7aR,12′aS,12′bS)-3,6,11′,12′b-Tetramethyl-2′,3′,3a,4,4′,4′a,5,5′,6,6′,6′a,6′b,7,7′,7a,8′,10′,12′,12′a,12′b-icosahydro-1′H,3H-spiro[furo[3,2-b]pyridine-2,9′-naphtho[2,1-a]azulen]-3′-yl]methanesulfonamide
Other names
saridegib
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • 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
    Key: HZLFFNCLTRVYJG-WWGOJCOQSA-N
  • C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC[C@@H]6C[C@@H](CC[C@@]6([C@H]5CC4=C(C3)C)C)NS(=O)(=O)C)C)NC1
Properties
C29H48N2O3S
Molar mass 504.77 g·mol−1
Pharmacology
Oral
Legal status
  • Investigational
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Saridegib, also known as IPI-926, is an experimental drug candidate undergoing clinical trials for the treatment of various types of cancer, including hard-to-treat hematologic malignancies such as myelofibrosis and ligand-dependent tumors such as chondrosarcoma.[1] IPI-926 exhibits its pharmacological effect by inhibition of the G protein-coupled receptor smoothened, a component of the hedgehog signaling pathway.[2] Chemically, it is a semi-synthetic derivative of the alkaloid cyclopamine. The process begins with cyclopamine extracted from harvested Veratrum californicum which is taken through a series of alterations resulting in an analogue of the natural product cyclopamine, making IPI-926 the only compound in development/testing that is not fully synthetic.[2]

Saridegib is a member of a class of anti-cancer compounds known as hedgehog pathway inhibitors.[citation needed]

References

  1. ^ "Pipeline: IPI-926". Infinity Pharmaceuticals. Archived from the original on 2012-01-19.
  2. ^ a b Tremblay, MR; Lescarbeau, A; Grogan, MJ; Tan, E; Lin, G; Austad, BC; Yu, LC; Behnke, ML; et al. (2009). "Discovery of a potent and orally active hedgehog pathway antagonist (IPI-926)". Journal of Medicinal Chemistry. 52 (14): 4400–18. doi:10.1021/jm900305z. PMID 19522463.