5N-Bicalutamide

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5N-Bicalutamide
Clinical data
Other names5-Azabicalutamide
Drug classNonsteroidal antiandrogen
ATC code
  • None
Identifiers
  • N-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methylpropanamide
JSmol)
  • CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CN=C(C(=C2)C(F)(F)F)C#N)O
  • InChI=1S/C17H13F4N3O4S/c1-16(26,9-29(27,28)12-4-2-10(18)3-5-12)15(25)24-11-6-13(17(19,20)21)14(7-22)23-8-11/h2-6,8,26H,9H2,1H3,(H,24,25)
  • Key:JWQMHMGGGRQTSY-UHFFFAOYSA-N

5N-Bicalutamide, or 5-azabicalutamide, is a highly potent

mutated prostate cancer cells are planned or underway and it is anticipated that N-bicalutamide may be able to overcome resistance.[1] to current antiandrogens that are used in the treatment of prostate cancer.[1]

second-generation NSAAs like RD-162 and apalutamide were derived from bicalutamide and as a result are similar to it in chemical structure.[1] They have up to about 10-fold higher affinity for the AR than does bicalutamide and hence are comparatively more potent and efficacious antiandrogens.[1] However, their structures are rigidified such that the analogous structural modification that was done with bicalutamide to create 5N-bicalutamide could not be used to increase affinity or potency with them.[1] Enzalutamide was described in 2013 as "the emperor of all antiandrogens" and other second-generation NSAAs have similar potency to it,[3] so 5N-bicalutamide would appear to be among the most potent AR antagonists to have been developed thus far.[1]

See also

References

  1. ^
    S2CID 24974359
    .
  2. ^ US Patent 10053433B2, England, Pamela M.; Fletterick, R. J. & Kuchenbecker, K. et al., published 2016 
  3. PMID 24076589
    .
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