N-Desmethylapalutamide

N-Desmethylapalutamide is a nonsteroidal antiandrogen (NSAA) and the major active metabolite of apalutamide, an NSAA which is used as a hormonal antineoplastic agent in the treatment of metastatic prostate cancer.[2][1] It has similar activity to that of apalutamide and, with apalutamide therapy, circulates at similar concentrations to those of apalutamide at steady state.[1] N-Desmethylapalutamide is formed from apalutamide in the liver by the cytochrome P450 enzymes CYP2C8 and CYP3A4.[1]

N-Desmethylapalutamide
Clinical data
Other namesDesmethylapalutamide; Norapalutamide
Drug classNonsteroidal antiandrogen
Pharmacokinetic data
Protein binding95%[1]
Identifiers
IUPAC name
  • 4-[7-[6-Cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluorobenzamide
PubChem CID
Chemical and physical data
FormulaC20H13F4N5O2S
Molar mass463.41 g·mol−1
3D model (JSmol)
SMILES
  • C1CC2(C1)C(=O)N(C(=S)N2C3=CC(=C(C=C3)C(=O)N)F)C4=CN=C(C(=C4)C(F)(F)F)C#N
InChI
  • InChI=1S/C20H13F4N5O2S/c21-14-7-10(2-3-12(14)16(26)30)29-18(32)28(17(31)19(29)4-1-5-19)11-6-13(20(22,23)24)15(8-25)27-9-11/h2-3,6-7,9H,1,4-5H2,(H2,26,30)
  • Key:BAANHOAPFBHUDX-UHFFFAOYSA-N

References
  1. "ERLEADATM (apalutamide) tablets, for oral use" (PDF). Janssen Biotech, Inc. U.S. Food and Drug Administration.
  2. Pérez-Ruixo C, Pérez-Blanco JS, Chien C, Yu M, Ouellet D, Pérez-Ruixo JJ, Ackaert O (February 2020). "Population Pharmacokinetics of Apalutamide and its Active Metabolite N-Desmethyl-Apalutamide in Healthy and Castration-Resistant Prostate Cancer Subjects". Clinical Pharmacokinetics. 59 (2): 229–244. doi:10.1007/s40262-019-00808-7. PMID 31432469. S2CID 201065140.


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