Apalutamide

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Apalutamide
File:Apalutamide.svg
Systematic (IUPAC) name
4-[7-[6-Cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide
Clinical data
Pregnancy
category
  • X (Contraindicated)
Routes of
administration		 Oral
Identifiers
CAS Number 956104-40-8
ATC code None
PubChem CID: 24872560
ChemSpider 28424131
Chemical data
Formula C21H15F4N5O2S
Molecular mass 477.434713 g/mol
  • CNC(=O)C1=C(C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CN=C(C(=C4)C(F)(F)F)C#N)F
  • InChI=1S/C21H15F4N5O2S/c1-27-17(31)13-4-3-11(8-15(13)22)30-19(33)29(18(32)20(30)5-2-6-20)12-7-14(21(23,24)25)16(9-26)28-10-12/h3-4,7-8,10H,2,5-6H2,1H3,(H,27,31)
  • Key:HJBWBFZLDZWPHF-UHFFFAOYSA-N

Apalutamide (INN) (developmental code name ARN-509, also JNJ-56021927) is a non-steroidal antiandrogen that is under development for the treatment of prostate cancer.[1] It is similar to enzalutamide both structurally and pharmacologically,[2] acting as a selective competitive antagonist of the androgen receptor (AR), but shows some advantages, including greater potency and reduced central nervous system permeation.[1][3][4] Apalutamide binds weakly to the GABAA receptor similarly to enzalutamide, but due to its relatively lower central concentrations, may have a lower risk of seizures in comparison.[1][3][5] The drug has been found to be effective and well-tolerated in clinical trials thus far,[2][4] with the most common side effects reported including fatigue, nausea, abdominal pain, and diarrhea.[6][3][5] Apalutamide is currently in phase III clinical trials for castration-resistant prostate cancer.[7]

Recently, the acquired F876L mutation of the AR identified in advanced prostate cancer cells was found to confer resistance to both enzalutamide and apalutamide.[8][9] A newer antiandrogen, ODM-201, is not affected by this mutation, nor has it been found to be affected by any other tested/well-known AR mutations.[10]

Apalutamide may be effective in a subset of prostate cancer patients with acquired resistance to abiraterone acetate.[2]

See also

References

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External links



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  2. ↑ 2.0 2.1 2.2 Lua error in package.lua at line 80: module 'strict' not found.
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