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N-Desmethylapalutamide

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(Redirected from N-desmethylapalutamide) Chemical compound Pharmaceutical compound
N-Desmethylapalutamide
Clinical data
Other namesDesmethylapalutamide; Norapalutamide
Drug classNonsteroidal antiandrogen
Pharmacokinetic data
Protein binding95%
Identifiers
IUPAC name
  • 4--8-oxo-6-sulfanylidene-5,7-diazaspirooctan-5-yl]-2-fluorobenzamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H13F4N5O2S
Molar mass463.41 g·mol
3D model (JSmol)
SMILES
  • C1CC2(C1)C(=O)N(C(=S)N2C3=CC(=C(C=C3)C(=O)N)F)C4=CN=C(C(=C4)C(F)(F)F)C#N
InChI
  • InChI=1S/C20H13F4N5O2S/c21-14-7-10(2-3-12(14)16(26)30)29-18(32)28(17(31)19(29)4-1-5-19)11-6-13(20(22,23)24)15(8-25)27-9-11/h2-3,6-7,9H,1,4-5H2,(H2,26,30)
  • Key:BAANHOAPFBHUDX-UHFFFAOYSA-N

N-Desmethylapalutamide is a nonsteroidal antiandrogen (NSAA) and the major active metabolite of apalutamide, an NSAA which is used as a hormonal antineoplastic agent in the treatment of metastatic prostate cancer. It has similar activity to that of apalutamide and, with apalutamide therapy, circulates at similar concentrations to those of apalutamide at steady state. N-Desmethylapalutamide is formed from apalutamide in the liver by the cytochrome P450 enzymes CYP2C8 and CYP3A4.

References

  1. ^ "ERLEADATM (apalutamide) tablets, for oral use" (PDF). Janssen Biotech, Inc. U.S. Food and Drug Administration.
  2. Pérez-Ruixo C, Pérez-Blanco JS, Chien C, Yu M, Ouellet D, Pérez-Ruixo JJ, Ackaert O (February 2020). "Population Pharmacokinetics of Apalutamide and its Active Metabolite N-Desmethyl-Apalutamide in Healthy and Castration-Resistant Prostate Cancer Subjects". Clinical Pharmacokinetics. 59 (2): 229–244. doi:10.1007/s40262-019-00808-7. PMID 31432469. S2CID 201065140.
Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids


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