N-Desmethylenzalutamide - Misplaced Pages

(Redirected from N-desmethylenzalutamide) Chemical compound Pharmaceutical compound

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--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
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).

References

^ "XTANDI® (enzalutamide)" (PDF). Archived (PDF) from the original on 27 August 2021. Retrieved 10 July 2024.
^ 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.
^ 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.
^ 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.

ARTooltip Androgen receptor

Agonists

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
5α-Dihydronormethandrone

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone

SARMsTooltip Selective androgen receptor modulator

Antagonists

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

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