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RU-58841

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
RU-58841
Clinical data
Other namesPSK-3841; HMR-3841
Drug classNonsteroidal antiandrogen
Identifiers
  • 4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)benzonitrile
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H18F3N3O3
Molar mass369.344 g·mol−1
3D model (JSmol)
  • CC1(C(=O)N(C(=O)N1CCCCO)C2=CC(=C(C=C2)C#N)C(F)(F)F)C
  • 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

RU-58841, also known asPSK-3841 orHMR-3841, is anonsteroidal antiandrogen (NSAA) which was initially developed in the 1980s byRoussel 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 atopical treatment forandrogen-dependent conditions includingacne,pattern hair loss,[1] andexcessive hair growth.[2][3][1] The compound is similar in structure to the NSAARU-58642 but contains a differentside-chain.[4] These compounds are similar inchemical structure tonilutamide,[5] which is related toflutamide,bicalutamide, andenzalutamide, all of which are NSAAs similarly.[6] RU-58841 can besynthesized either by building thehydantoinmoiety or byarylcoupling to 5,5-dimethylhydantoin.[7]

RU-58841 producescyanonilutamide (RU-56279) and RU-59416 asmetabolites in animals.[8] Cyanonilutamide has relatively low affinity for the androgen receptor but shows significantantiandrogenic activity in animals.[8] RU-59416 has very low affinity for the androgen receptor.[8]

See also

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References

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  1. ^abMünster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, et al. (January 2005)."RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia".Die Pharmazie.60 (1):8–12.PMID 15700772.
  2. ^"PSK-3841 (HMR-3841, RU-58841)".AdisInsight. Springer Nature Switzerland AG.
  3. ^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".The Journal of Steroid Biochemistry and Molecular Biology.48 (1):55–60.doi:10.1016/0960-0760(94)90250-X.PMID 8136306.S2CID 31052540.
  4. ^Van Dort ME, Jung YW (April 2001). "Synthesis and structure-activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands".Bioorganic & Medicinal Chemistry Letters.11 (8):1045–1047.doi:10.1016/s0960-894x(01)00146-9.PMID 11327585.
  5. ^Poulos GA, Mirmirani P (February 2005). "Investigational medications in the treatment of alopecia".Expert Opinion on Investigational Drugs.14 (2):177–184.doi:10.1517/13543784.14.2.177.PMID 15757393.S2CID 24694921.
  6. ^Elancheran R, Maruthanila VL, Ramanathan M, Kabilan S, Devi R, Kunnumakara A, Kotoky J (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.
  7. ^Leonard MJ, Lingham AR, Niere JO, Jackson NR, McKay PG, Hügel HM (2014)."Alternative synthesis of the anti-baldness compound RU58841".RSC Adv.4 (27):14143–14148.Bibcode:2014RSCAd...414143L.doi:10.1039/C4RA00332B.ISSN 2046-2069.
  8. ^abcCousty-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".The Journal of Steroid Biochemistry and Molecular Biology.51 (1–2):47–55.doi:10.1016/0960-0760(94)90114-7.PMID 7947350.S2CID 29752252.

Further reading

[edit]
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
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