RU-58841
RU-58841, also known as PSK-3841 or HMR-3841, is a nonsteroidal antiandrogen (NSAA) which was initially developed in the 1980s. 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][4][5] The compound is similar in structure to the NSAA RU-58642 but contains a different side-chain.[6] These compounds are similar in chemical structure to nilutamide,[7] which is related to flutamide, bicalutamide, and enzalutamide, all of which are NSAAs similarly.[8] RU-58841 can be synthesized either by building the hydantoin moiety or by aryl coupling to 5,5-dimethylhydantoin.[9]
 | |
| Clinical data | |
|---|---|
| Other names | PSK-3841; HMR-3841 |
| Drug class | Nonsteroidal antiandrogen |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C17H18F3N3O3 |
| Molar mass | 369.344 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
RU-58841 produces cyanonilutamide (RU-56279) and RU-59416 as metabolites in animals.[10] Cyanonilutamide has relatively low affinity for the androgen receptor but shows significant antiandrogenic activity in animals.[10] RU-59416 has very low affinity for the androgen receptor.[10]
See also
References
- "RU58841 studies and information". Anagen.
- PSK-3841 (HMR-3841, RU-58841) - AdisInsight
- Battmann T, 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". J. Steroid Biochem. Mol. Biol. 48 (1): 55–60. doi:10.1016/0960-0760(94)90250-X. PMID 8136306. S2CID 31052540.
- Münster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, Schaller M, Korting HC, Zouboulis C, 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.
- "RU58841 for Hair Loss – Underused Finasteride Alternative?". Hairverse. 2019-03-10. Retrieved 2020-07-14.
- Van Dort ME, Jung YW (April 2001). "Synthesis and structure-activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands". Bioorg. Med. Chem. Lett. 11 (8): 1045–7. doi:10.1016/s0960-894x(01)00146-9. PMID 11327585.
- Poulos GA, Mirmirani P (February 2005). "Investigational medications in the treatment of alopecia". Expert Opin Investig Drugs. 14 (2): 177–84. doi:10.1517/13543784.14.2.177. PMID 15757393. S2CID 24694921.
- Elancheran, R.; Maruthanila, V. L.; Ramanathan, M.; Kabilan, S.; Devi, R.; Kunnumakara, A.; Kotoky, Jibon (2015). "Recent discoveries and developments of androgen receptor based therapy for prostate cancer". MedChemComm. 6 (5): 746–768. doi:10.1039/C4MD00416G. ISSN 2040-2503. S2CID 72654573.
- Leonard, Matthew J.; Lingham, Anthony R.; Niere, Julie O.; Jackson, Neale R. C.; McKay, Peter G.; Hügel, Helmut M. (2014). "Alternative synthesis of the anti-baldness compound RU58841". RSC Adv. 4 (27): 14143–14148. doi:10.1039/C4RA00332B. ISSN 2046-2069.
- 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. S2CID 29752252.
Further reading
- Münster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, Schaller M, Korting HC, Zouboulis CC, 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.