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. It has similar activity to that of enzalutamide and, with enzalutamide therapy, circulates at similar concentrations to those of enzalutamide at steady state. N-Desmethylenzalutamide is formed from enzalutamide in the liver by the cytochrome P450 enzymes CYP2C8 and CYP3A4. It has a longer terminal half-life than enzalutamide (7.8 days versus 5.8 days).