RU-56187

RU-56187 is a nonsteroidal antiandrogen which was never marketed.[1][2][3][4][5] It shows 92% of the affinity of testosterone for the androgen receptor and negligible affinity for other steroid hormone receptors.[1][2] The medication is a silent antagonist of the androgen receptor.[5] RU-56187 is 3- to 10-fold more potent as an antiandrogen than bicalutamide or nilutamide in animals.[1] Both RU-56187 and RU-58841 appear to be prodrugs of cyanonilutamide (RU-56279) in vivo in animals.[3]

Affinities of a selection of androgen receptor
ligands at steroid hormone receptors
CompoundARERPRGRMR
Metribolone290< 0.1190438
Dihydrotestosterone180????
Testosterone100????
Cyproterone acetate10????
Bicalutamide1.8????
Nilutamide0.8????
Hydroxyflutamide0.8????
RU-59063300<0.1<0.1<0.1<0.1
RU-58841150????
RU-5864246<0.1<0.1<0.1<0.1
RU-57073163<0.1<0.1<0.1<0.1
RU-5618792<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.
RU-56187
Clinical data
Drug classNonsteroidal antiandrogen
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC14H12F3N3OS
Molar mass327.325 g/mol g·mol−1
3D model (JSmol)

See also

References
  1. Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Curr. Med. Chem. 7 (2): 211–47. doi:10.2174/0929867003375371. PMID 10637363.
  2. Teutsch G, Goubet F, Battmann T, Bonfils A, Bouchoux F, Cerede E, Gofflo D, Gaillard-Kelly M, Philibert D (January 1994). "Non-steroidal antiandrogens: synthesis and biological profile of high-affinity ligands for the androgen receptor". J. Steroid Biochem. Mol. Biol. 48 (1): 111–9. doi:10.1016/0960-0760(94)90257-7. PMID 8136296.
  3. 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.
  4. Matias JR, Gaillard M (June 1995). "Local inhibition of sebaceous gland growth by topically applied RU 58841". Ann. N. Y. Acad. Sci. 761: 56–65. doi:10.1111/j.1749-6632.1995.tb31369.x. PMID 7625751.
  5. Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM (March 1999). "Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone". Mol. Endocrinol. 13 (3): 440–54. doi:10.1210/mend.13.3.0255. PMID 10077001.


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