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.[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 names	Desmethylapalutamide; Norapalutamide
Drug class	Nonsteroidal antiandrogen
Pharmacokinetic data
Protein binding	95%[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	86683490
Chemical and physical data
Formula	C20H13F4N5O2S
Molar mass	463.411 g/mol 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