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'''RU-58841''', also known as '''PSK-3841''' or '''HMR-3841''', is a [[nonsteroidal antiandrogen]] (NSAA) which was initially developed in the 1980s by [[Roussell 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 medication|topical]] treatment for [[androgen-dependent condition]]s including [[acne]], [[pattern hair loss]],<ref>{{cite web |title=RU58841 studies and information |url=https://www.anagen.com/blogs/hair-loss-blog/ru58841-for-hair-loss-what-is-it |website=Anagen |language=en}}</ref> and [[hirsutism|excessive hair growth]].<ref name="AdisInsight">[http://adisinsight.springer.com/drugs/800005990 PSK-3841 (HMR-3841, RU-58841) - AdisInsight]</ref><ref name="pmid8136306">{{cite journal | vauthors = Battmann T, Bonfils A, Branche C, Humbert J, Goubet F, Teutsch G, Philibert D | title = RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism | journal = J. Steroid Biochem. Mol. Biol. | volume = 48 | issue = 1 | pages = 55–60 | date = January 1994 | pmid = 8136306 | doi = 10.1016/0960-0760(94)90250-X | s2cid = 31052540 }}</ref><ref name="pmid15700772">{{cite journal | vauthors = Münster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, Schaller M, Korting HC, Zouboulis C, Blume-Peytavi U, Schäfer-Korting M | title = RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia | journal = Pharmazie | volume = 60 | issue = 1 | pages = 8–12 | date = January 2005 | pmid = 15700772 | url = http://www.ingentaconnect.com/content/govi/pharmaz/2005/00000060/00000001/art00002}}</ref><ref>{{Cite web|date=2019-03-10|title=RU58841 for Hair Loss – Underused Finasteride Alternative?|url=https://hairverse.com/ru58841/|access-date=2020-07-14|website=Hairverse|language=en-US}}</ref> The compound is similar in structure to the NSAA [[RU-58642]] but contains a different [[side chain|side-chain]].<ref name="pmid11327585">{{cite journal | vauthors = Van Dort ME, Jung YW | title = Synthesis and structure-activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands | journal = Bioorg. Med. Chem. Lett. | volume = 11 | issue = 8 | pages = 1045–7 | date = April 2001 | pmid = 11327585 | doi = 10.1016/s0960-894x(01)00146-9 }}</ref> These compounds are similar in [[chemical structure]] to [[nilutamide]],<ref name="pmid15757393">{{cite journal | vauthors = Poulos GA, Mirmirani P | title = Investigational medications in the treatment of alopecia | journal = Expert Opin Investig Drugs | volume = 14 | issue = 2 | pages = 177–84 | date = February 2005 | pmid = 15757393 | doi = 10.1517/13543784.14.2.177 | s2cid = 24694921 }}</ref> which is related to [[flutamide]], [[bicalutamide]], and [[enzalutamide]], all of which are NSAAs similarly.<ref name="ElancheranMaruthanila2015">{{cite journal|last1=Elancheran|first1=R.|last2=Maruthanila|first2=V. L.|last3=Ramanathan|first3=M.|last4=Kabilan|first4=S.|last5=Devi|first5=R.|last6=Kunnumakara|first6=A.|last7=Kotoky|first7=Jibon|title=Recent discoveries and developments of androgen receptor based therapy for prostate cancer|journal=MedChemComm|volume=6|issue=5|year=2015|pages=746–768|issn=2040-2503|doi=10.1039/C4MD00416G|s2cid=72654573|url=https://semanticscholar.org/paper/39b718b11cf367476218d3b8a8cb0574392262b9}}</ref> RU-58841 can be [[chemical synthesis|synthesized]] either by building the [[hydantoin]] [[moiety (chemistry)|moiety]] or by [[aryl group|aryl]] [[coupling reaction|coupling]] to 5,5-dimethylhydantoin.<ref name="LeonardLingham2014">{{cite journal|last1=Leonard|first1=Matthew J.|last2=Lingham|first2=Anthony R.|last3=Niere|first3=Julie O.|last4=Jackson|first4=Neale R. C.|last5=McKay|first5=Peter G.|last6=Hügel|first6=Helmut M.|title=Alternative synthesis of the anti-baldness compound RU58841|journal=RSC Adv.|volume=4|issue=27|year=2014|pages=14143–14148|issn=2046-2069|doi=10.1039/C4RA00332B}}</ref>
'''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 medication|topical]] treatment for [[androgen-dependent condition]]s including [[acne]], [[pattern hair loss]],<ref>{{cite web |title=RU58841 studies and information |url=https://www.anagen.com/blogs/hair-loss-blog/ru58841-for-hair-loss-what-is-it |website=Anagen |language=en}}</ref> and [[hirsutism|excessive hair growth]].<ref name="AdisInsight">[http://adisinsight.springer.com/drugs/800005990 PSK-3841 (HMR-3841, RU-58841) - AdisInsight]</ref><ref name="pmid8136306">{{cite journal | vauthors = Battmann T, Bonfils A, Branche C, Humbert J, Goubet F, Teutsch G, Philibert D | title = RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism | journal = J. Steroid Biochem. Mol. Biol. | volume = 48 | issue = 1 | pages = 55–60 | date = January 1994 | pmid = 8136306 | doi = 10.1016/0960-0760(94)90250-X | s2cid = 31052540 }}</ref><ref name="pmid15700772">{{cite journal | vauthors = Münster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, Schaller M, Korting HC, Zouboulis C, Blume-Peytavi U, Schäfer-Korting M | title = RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia | journal = Pharmazie | volume = 60 | issue = 1 | pages = 8–12 | date = January 2005 | pmid = 15700772 | url = http://www.ingentaconnect.com/content/govi/pharmaz/2005/00000060/00000001/art00002}}</ref><ref>{{Cite web|date=2019-03-10|title=RU58841 for Hair Loss – Underused Finasteride Alternative?|url=https://hairverse.com/ru58841/|access-date=2020-07-14|website=Hairverse|language=en-US}}</ref> The compound is similar in structure to the NSAA [[RU-58642]] but contains a different [[side chain|side-chain]].<ref name="pmid11327585">{{cite journal | vauthors = Van Dort ME, Jung YW | title = Synthesis and structure-activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands | journal = Bioorg. Med. Chem. Lett. | volume = 11 | issue = 8 | pages = 1045–7 | date = April 2001 | pmid = 11327585 | doi = 10.1016/s0960-894x(01)00146-9 }}</ref> These compounds are similar in [[chemical structure]] to [[nilutamide]],<ref name="pmid15757393">{{cite journal | vauthors = Poulos GA, Mirmirani P | title = Investigational medications in the treatment of alopecia | journal = Expert Opin Investig Drugs | volume = 14 | issue = 2 | pages = 177–84 | date = February 2005 | pmid = 15757393 | doi = 10.1517/13543784.14.2.177 | s2cid = 24694921 }}</ref> which is related to [[flutamide]], [[bicalutamide]], and [[enzalutamide]], all of which are NSAAs similarly.<ref name="ElancheranMaruthanila2015">{{cite journal|last1=Elancheran|first1=R.|last2=Maruthanila|first2=V. L.|last3=Ramanathan|first3=M.|last4=Kabilan|first4=S.|last5=Devi|first5=R.|last6=Kunnumakara|first6=A.|last7=Kotoky|first7=Jibon|title=Recent discoveries and developments of androgen receptor based therapy for prostate cancer|journal=MedChemComm|volume=6|issue=5|year=2015|pages=746–768|issn=2040-2503|doi=10.1039/C4MD00416G|s2cid=72654573|url=https://semanticscholar.org/paper/39b718b11cf367476218d3b8a8cb0574392262b9}}</ref> RU-58841 can be [[chemical synthesis|synthesized]] either by building the [[hydantoin]] [[moiety (chemistry)|moiety]] or by [[aryl group|aryl]] [[coupling reaction|coupling]] to 5,5-dimethylhydantoin.<ref name="LeonardLingham2014">{{cite journal|last1=Leonard|first1=Matthew J.|last2=Lingham|first2=Anthony R.|last3=Niere|first3=Julie O.|last4=Jackson|first4=Neale R. C.|last5=McKay|first5=Peter G.|last6=Hügel|first6=Helmut M.|title=Alternative synthesis of the anti-baldness compound RU58841|journal=RSC Adv.|volume=4|issue=27|year=2014|pages=14143–14148|issn=2046-2069|doi=10.1039/C4RA00332B}}</ref>


RU-58841 produces [[cyanonilutamide]] (RU-56279) and RU-59416 as [[metabolite]]s in animals.<ref name="pmid7947350">{{cite journal | vauthors = Cousty-Berlin D, Bergaud B, Bruyant MC, Battmann T, Branche C, Philibert D | title = Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite | journal = J. Steroid Biochem. Mol. Biol. | volume = 51 | issue = 1–2 | pages = 47–55 | date = October 1994 | pmid = 7947350 | doi = 10.1016/0960-0760(94)90114-7 | s2cid = 29752252 }}</ref> Cyanonilutamide has relatively low affinity for the androgen receptor but shows significant [[antiandrogen]]ic activity in animals.<ref name="pmid7947350" /> RU-59416 has very low affinity for the androgen receptor.<ref name="pmid7947350" />
RU-58841 produces [[cyanonilutamide]] (RU-56279) and RU-59416 as [[metabolite]]s in animals.<ref name="pmid7947350">{{cite journal | vauthors = Cousty-Berlin D, Bergaud B, Bruyant MC, Battmann T, Branche C, Philibert D | title = Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite | journal = J. Steroid Biochem. Mol. Biol. | volume = 51 | issue = 1–2 | pages = 47–55 | date = October 1994 | pmid = 7947350 | doi = 10.1016/0960-0760(94)90114-7 | s2cid = 29752252 }}</ref> Cyanonilutamide has relatively low affinity for the androgen receptor but shows significant [[antiandrogen]]ic activity in animals.<ref name="pmid7947350" /> RU-59416 has very low affinity for the androgen receptor.<ref name="pmid7947350" />

Revision as of 23:37, 27 February 2021

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
PubChem CID
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 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][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]

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

  1. ^ "RU58841 studies and information". Anagen.
  2. ^ PSK-3841 (HMR-3841, RU-58841) - AdisInsight
  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". J. Steroid Biochem. Mol. Biol. 48 (1): 55–60. doi:10.1016/0960-0760(94)90250-X. PMID 8136306. S2CID 31052540.
  4. ^ 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.
  5. ^ "RU58841 for Hair Loss – Underused Finasteride Alternative?". Hairverse. 2019-03-10. Retrieved 2020-07-14.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ a b c 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

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