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N-Desmethylenzalutamide

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
N-Desmethylenzalutamide
Clinical data
Other namesDesmethylenzalutamide; Norenzalutamide
Drug classNonsteroidal antiandrogen
Pharmacokinetic data
Protein binding95%[1]
Eliminationhalf-life7.8 days[2][1]
Identifiers
  • 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-fluorobenzamide
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H14F4N4O2S
Molar mass450.41 g·mol−1
3D model (JSmol)
  • 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=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 anonsteroidal antiandrogen (NSAA) and the majormetabolite ofenzalutamide, an NSAA which is used as ahormonal antineoplastic agent in the treatment ofmetastaticprostate cancer.[3][4][2] It has similar activity to that of enzalutamide and, with enzalutamide therapy, circulates at similar concentrations to those of enzalutamide atsteady state.[3][4][2]N-Desmethylenzalutamide is formed from enzalutamide in theliver by thecytochrome P450enzymesCYP2C8 andCYP3A4.[4] It has a longerterminal half-life than enzalutamide (7.8 days versus 5.8 days).[2]

References

[edit]
  1. ^ab"XTANDI® (enzalutamide)"(PDF).Archived(PDF) from the original on 27 August 2021. Retrieved10 July 2024.
  2. ^abcdBenoist 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. ^abKeating 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. ^abcEl-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.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists


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