RU-58841

RU-58841, also known as PSK-3841 or HMR-3841, is a nonsteroidal antiandrogen (NSAA) which was initially developed in the 1980s by Roussel Uclaf, the French pharmaceutical company from which it received its name. It was formerly under investigation by ProStrakan (previously ProSkelia and Strakan) for potential use as a topical treatment for androgen-dependent conditions including acne, pattern hair loss,^[1] and excessive hair growth.^[2][3][1] The compound is similar in structure to the NSAA RU-58642 but contains a different side-chain.^[4] These compounds are similar in chemical structure to nilutamide,^[5] which is related to flutamide, bicalutamide, and enzalutamide, all of which are NSAAs similarly.^[6] RU-58841 can be synthesized either by building the hydantoin moiety or by aryl coupling to 5,5-dimethylhydantoin.^[7]

Other namesPSK-3841; HMR-3841

Drug classNonsteroidal antiandrogen

CAS Number

• 154992-24-2

PubChem CID

• 132981

Quick facts Clinical data, Other names ...

RU-58841

Clinical data
Other names	PSK-3841; HMR-3841
Drug class	Nonsteroidal antiandrogen
Identifiers
IUPAC name 4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)benzonitrile
CAS Number	154992-24-2
PubChem CID	132981
ChemSpider	117358
UNII	0D8FJQ0ADW
ChEMBL	ChEMBL9337
CompTox Dashboard (EPA)	DTXSID20165781
Chemical and physical data
Formula	C17H18F3N3O3
Molar mass	369.344 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1(C(=O)N(C(=O)N1CCCCO)C2=CC(=C(C=C2)C#N)C(F)(F)F)C
InChI InChI=1S/C17H18F3N3O3/c1-16(2)14(25)23(15(26)22(16)7-3-4-8-24)12-6-5-11(10-21)13(9-12)17(18,19)20/h5-6,9,24H,3-4,7-8H2,1-2H3 Key:ARBYGDBJECGMGA-UHFFFAOYSA-N

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RU-58841 produces cyanonilutamide (RU-56279) and RU-59416 as metabolites in animals.^[8] Cyanonilutamide has relatively low affinity for the androgen receptor but shows significant antiandrogenic activity in animals.^[8] RU-59416 has very low affinity for the androgen receptor.^[8]