N-Desmethylenzalutamide

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]

N-Desmethylenzalutamide
Clinical data
Other namesDesmethylenzalutamide; Norenzalutamide
Drug classNonsteroidal antiandrogen
Pharmacokinetic data
Protein binding95%[1]
Elimination half-life7.8 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
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC20H14F4N4O2S
Molar mass450.41 g·mol−1
3D model (JSmol)
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

References
  1. https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/203415s011lbl.pdf
  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: 235–45. doi:10.4137/CMO.S11670. PMC 3813614. PMID 24179414.


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