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

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.

RU-56187

Clinical data
Drug class	Nonsteroidal antiandrogen
Identifiers
IUPAC name 2-(Trifluoromethyl)-4-(3,4,4-trimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl)benzonitrile
CAS Number	143782-25-6
PubChem CID	132581
ChemSpider	117054
ChEMBL	ChEMBL1099140
CompTox Dashboard (EPA)	DTXSID90162545
Chemical and physical data
Formula	C14H12F3N3OS
Molar mass	327.33 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC1(C(=O)N(C(=S)N1C)C2=CC(=C(C=C2)C#N)C(F)(F)F)C
InChI InChI=1S/C14H12F3N3OS/c1-13(2)11(21)20(12(22)19(13)3)9-5-4-8(7-18)10(6-9)14(15,16)17/h4-6H,1-3H3 Key:HLBUAKQNKJTEIU-UHFFFAOYSA-N

See also

• RU-57073
• RU-58642
• RU-59063

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.