N-Desmethylenzalutamide

N-Desmethylenzalutamide

Clinical data
Other names	Desmethylenzalutamide; Norenzalutamide
Drug class	Nonsteroidal antiandrogen
Pharmacokinetic data
Protein binding	95% [1]
Elimination half-life	7.8 days [2] [1]
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  Y
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]

References

1. "XTANDI® (enzalutamide)" (PDF). Archived (PDF) from the original on 27 August 2021. Retrieved 10 July 2024.
2. Benoist GE, Hendriks RJ, Mulders PF, Gerritsen WR, Somford DM, Schalken JA, van Oort IM, Burger DM, van Erp NP (2016). "Pharmacokinetic Aspects of the Two Novel Oral Drugs Used for Metastatic Castration-Resistant Prostate Cancer: Abiraterone Acetate and Enzalutamide". Clin Pharmacokinet. 55 (11): 1369–1380. doi:10.1007/s40262-016-0403-6. PMC   5069300 . PMID   27106175.
3. Keating GM (2015). "Enzalutamide: a review of its use in chemotherapy-naïve metastatic castration-resistant prostate cancer". Drugs Aging. 32 (3): 243–9. doi:10.1007/s40266-015-0248-y. PMID   25711765. S2CID   29563345.
4. El-Amm J, Patel N, Freeman A, Aragon-Ching JB (2013). "Metastatic castration-resistant prostate cancer: critical review of enzalutamide". Clin Med Insights Oncol. 7 CMO.S11670: 235–45. doi:10.4137/CMO.S11670. PMC   3813614 . PMID   24179414.