RU-58841
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Systematic (IUPAC) name | |
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4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)benzonitrile | |
Identifiers | |
CAS Number | 154992-24-2 |
PubChem | CID 132981 |
Chemical data | |
Formula | C17H18F3N3O3 |
Molar mass | 369.3 g/mol |
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RU-58841 is an experimental drug candidate which is intended 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 non-steroidal anti-androgen drugs similar to nilutamide,[4] which is related to flutamide, bicalutamide, and enzalutamide. RU58841 can be synthesized either by building the hydantoin moiety or by aryl coupling to 5,5-dimethylhydantoin [5]
Synthesis
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RU58841 synthesis (traditional):[1]
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RU58841 synthesis alternative:[5]
References
- 1 2 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.
- ↑ 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.
- ↑ 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.
- ↑ "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.
- 1 2 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.
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