Cyanonilutamide

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Cyanonilutamide
Cyanonilutamide.svg
Clinical data
SynonymsRU-56279
Drug classNonsteroidal antiandrogen
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H10F3N3O2
Molar mass297.237 g·mol−1
3D model (JSmol)

Cyanonilutamide (developmental code name RU-56279) is a nonsteroidal antiandrogen which was never marketed.[1][2] Both RU-56187 and RU-58841 appear to be prodrugs of cyanonilutamide in vivo in animals.[2] It has relatively low affinity for the androgen receptor but nonetheless shows significant antiandrogenic activity in animals.[2]

Affinities of a selection of androgen receptor
ligands at steroid hormone receptors

Compound AR ER PR GR MR
Metribolone 290 < 0.1 190 4 38
Dihydrotestosterone 180 ? ? ? ?
Testosterone 100 ? ? ? ?
Cyproterone acetate 10 ? ? ? ?
Bicalutamide 1.8 ? ? ? ?
Nilutamide 0.8 ? ? ? ?
Hydroxyflutamide 0.8 ? ? ? ?
RU-59063 300 <0.1 <0.1 <0.1 <0.1
RU-58841 150 ? ? ? ?
RU-58642 46 <0.1 <0.1 <0.1 <0.1
RU-57073 163 <0.1 <0.1 <0.1 <0.1
RU-56187 92 <0.1 <0.1 <0.1 <0.1
Notes: Values are RBAs (%). Reference ligands (100%) were testosterone for the AR, estradiol for the ERα and ERβ, progesterone for the PR, dexamethasone for the GR, and aldosterone for the MR. Sources: See template.

See also[edit]

References[edit]

  1. ^ Gryder BE, Akbashev MJ, Rood MK, Raftery ED, Meyers WM, Dillard P, Khan S, Oyelere AK (November 2013). "Selectively targeting prostate cancer with antiandrogen equipped histone deacetylase inhibitors". ACS Chem. Biol. 8 (11): 2550–60. doi:10.1021/cb400542w. PMC 3836611. PMID 24004176.
  2. ^ a b c Cousty-Berlin D, Bergaud B, Bruyant MC, Battmann T, Branche C, Philibert D (October 1994). "Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite". J. Steroid Biochem. Mol. Biol. 51 (1–2): 47–55. doi:10.1016/0960-0760(94)90114-7. PMID 7947350.