RU-58841

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RU-58841
RU-58841.svg
Systematic (IUPAC) name
4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)benzonitrile
Identifiers
CAS Number 154992-24-2
PubChem CID 132981
ChemSpider 117358
ChEMBL CHEMBL9337
Chemical data
Formula C17H18F3N3O3
Molar mass 369.3 g/mol

RU-58841 (also known as PSK-3841 or HMR-3841) is a non-steroidal antiandrogen which was previously investigated for use as a topical treatment for acne, androgenetic alopecia, and hirsutism.[1][2] The compound is similar in structure to RU-58642 but contains a different side-chain.[3] These compounds are similar in chemical structure to nilutamide,[4] which is related to flutamide, bicalutamide, and enzalutamide. RU-58841 can be synthesized either by building the hydantoin moiety or by aryl coupling to 5,5-dimethylhydantoin [5]

Synthesis[edit]

RU-58841 synthesis #1.[1]
RU-58841 synthesis #2.[5]

See also[edit]

References[edit]

  1. ^ a b Battmann, Bonfils A, Branche C, Humbert J, Goubet F, Teutsch G, Philibert D (January 1994). "RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism". Journal of Steroid Biochemistry and Molecular Biology. 48 (1): 55–60. doi:10.1016/0960-0760(94)90250-x. PMID 8136306. 
  2. ^ Münster U; Nakamura C; Haberland A; Jores K; Mehnert W; Rummel S; Schaller M; Korting HC; Zouboulis ChC; Blume-Peytavi U; Schäfer-Korting M (January 2005). "RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia". Pharmazie. 60 (1): 8–12. PMID 15700772. 
  3. ^ Van Dort ME, Jung YW (2001). "Synthesis and structure–activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands". Bioorg. Med. Chem. Lett. 11 (8): 1045–1047. doi:10.1016/s0960-894x(01)00146-9. PMID 11327585. 
  4. ^ "Investigational medications in the treatment of alopecia". Expert Opinion on Investigational Drugs. 14 (2): 177–184. February 2005. doi:10.1517/13543784.14.2.177. 
  5. ^ a b M. J. Leonard, A. R. Lingham, J. O. Niere, N. R. C. Jackson, P. G. McKay and H. M. Hϋgel (6 Mar 2014). "Alternative synthesis of the anti-baldness compound RU58841". RSC Advances. 4: 14143–14148. doi:10.1039/c4ra00332b.