N-Desmethylenzalutamide

N-Desmethylenzalutamide
Clinical data
Other names	Desmethylenzalutamide; Norenzalutamide
Drug class	Nonsteroidal antiandrogen
Pharmacokinetic data
Protein binding	95%
Elimination half-life	7.8 days
Identifiers
	IUPAC name 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-fluorobenzamide;
CAS Number	1242137-16-1 ;
PubChem CID	70678916;
ChemSpider	28533218;
UNII	567TX6UB9S;
ChEBI	CHEBI:68538;
CompTox Dashboard (EPA)	DTXSID601111408 ;
Chemical and physical data
Formula	C20H14F4N4O2S
Molar mass	450.41 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(C(=O)N(C(=S)N1C2=CC(=C(C=C2)C(=O)N)F)C3=CC(=C(C=C3)C#N)C(F)(F)F)C;
	InChI InChI=1S/C20H14F4N4O2S/c1-19(2)17(30)27(11-4-3-10(9-25)14(7-11)20(22,23)24)18(31)28(19)12-5-6-13(16(26)29)15(21)8-12/h3-8H,1-2H3,(H2,26,29); Key:JSFOGZGIBIQRPU-UHFFFAOYSA-N;

N-Desmethylenzalutamide is a nonsteroidal antiandrogen (NSAA) and the major metabolite of enzalutamide, an NSAA which is used as a hormonal antineoplastic agent in the treatment of metastatic prostate cancer.^[3]^[4]^[2] It has similar activity to that of enzalutamide and, with enzalutamide therapy, circulates at similar concentrations to those of enzalutamide at steady state.^[3]^[4]^[2] N-Desmethylenzalutamide is formed from enzalutamide in the liver by the cytochrome P450 enzymes CYP2C8 and CYP3A4.^[4] It has a longer terminal half-life than enzalutamide (7.8 days versus 5.8 days).^[2]