N-Desmethylapalutamide

N-Desmethylapalutamide
Clinical data
Other names	Desmethylapalutamide; Norapalutamide
Drug class	Nonsteroidal antiandrogen
Pharmacokinetic data
Protein binding	95%
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;
CAS Number	1332391-11-3 ;
PubChem CID	86683490;
ChemSpider	68007182;
UNII	13RV85F63R;
CompTox Dashboard (EPA)	DTXSID501336279 ;
Chemical and physical data
Formula	C20H13F4N5O2S
Molar mass	463.41 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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. It has similar activity to that of apalutamide and, with apalutamide therapy, circulates at similar concentrations to those of apalutamide at steady state. N-Desmethylapalutamide is formed from apalutamide in the liver by the cytochrome P450 enzymes CYP2C8 and CYP3A4.