RU-56187

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
RU-56187
RU-56187.svg
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)

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

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. ^ a b c 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. ^ a b 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. ^ a b 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. ^ a b 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.