RU-58642

RU-58642 is a nonsteroidal antiandrogen (NSAA) derived from nilutamide with very high affinity and selectivity for the androgen receptor (AR), which made it among the most potent and efficacious antiandrogens known at the time of its discovery.^[1] It was investigated for topical application for the treatment of androgenetic alopecia (male-pattern baldness), but development did not proceed past initial trial stages, and it is now only used for scientific research into the AR.^[2][3]

RU-58642

Clinical data
Drug class	Nonsteroidal antiandrogen
Identifiers
IUPAC name 4-[3-(cyanomethyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
CAS Number	143782-63-2 Y
PubChem CID	9840708
ChemSpider	8016425
UNII	DX44GS85HK
CompTox Dashboard (EPA)	DTXSID50162546
Chemical and physical data
Formula	C15H11F3N4O2
Molar mass	336.274 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C1N(CC#N)C(C)(C)C(=O)N1c(cc2C(F)(F)F)ccc2C#N
InChI InChI=1S/C15H11F3N4O2/c1-14(2)12(23)22(13(24)21(14)6-5-19)10-4-3-9(8-20)11(7-10)15(16,17)18/h3-4,7H,6H2,1-2H3 Key:ZVWXHSNUBLIKJH-UHFFFAOYSA-N

See also

• Cyanonilutamide
• RU-56187
• RU-57073
• RU-58841
• RU-59063

References

1. Battmann T, Branche C, Bouchoux F, Cerede E, Philibert D, Goubet F, Teutsch G, Gaillard-Kelly M (January 1998). "Pharmacological profile of RU 58642, a potent systemic antiandrogen for the treatment of androgen-dependent disorders". The Journal of Steroid Biochemistry and Molecular Biology. 64 (1–2): 103–11. doi:10.1016/S0960-0760(97)00151-9. PMID 9569015. S2CID 290926.
2. Sims NA, Clément-Lacroix P, Minet D, Fraslon-Vanhulle C, Gaillard-Kelly M, Resche-Rigon M, Baron R (May 2003). "A functional androgen receptor is not sufficient to allow estradiol to protect bone after gonadectomy in estradiol receptor-deficient mice". The Journal of Clinical Investigation. 111 (9): 1319–27. doi:10.1172/JCI17246. PMC 154447. PMID 12727923.
3. Windahl SH, Galien R, Chiusaroli R, Clément-Lacroix P, Morvan F, Lepescheux L, Nique F, Horne WC, Resche-Rigon M, Baron R (September 2006). "Bone protection by estrens occurs through non-tissue-selective activation of the androgen receptor". The Journal of Clinical Investigation. 116 (9): 2500–9. doi:10.1172/JCI28809. PMC 1555662. PMID 16955145.