Saridegib

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
Names
IUPAC name
N-[(5βH)-5,6-Dihydro-17,23β-epoxy-16a-homoveratraman-3α-yl]methanesulfonamide
Preferred 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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • 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
SMILES
  • [H][C@]12[C@@]([C@@]3([H])C(C2)=C(C)C[C@@]4(O[C@@](C[C@H](C)CN5)([H])[C@]5([H])[C@H]4C)CC3)([H])CC[C@]6([H])C[C@H](NS(C)(=O)=O)CC[C@@]61C
Properties
Chemical formula
 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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Infobox references

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

References
  1. "Pipeline: IPI-926". Infinity Pharmaceuticals. Archived from the original on 2012-01-19.{{cite web}}: CS1 maint: unfit URL (link)
  2. 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.
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