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Roxindole

From Wikipedia, the free encyclopedia
Dopaminergic & serotonergic drug developed for schizophrenia treatment
Pharmaceutical compound
Roxindole
Clinical data
Other namesEMD-49980; EMD49980
ATC code
  • None
Identifiers
  • 3-[4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)butyl]-1H-indol-5-ol
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H26N2O
Molar mass346.474 g·mol−1
3D model (JSmol)
  • Oc1ccc2c(c1)c(c[nH]2)CCCCN4C/C=C(/c3ccccc3)CC4

Roxindole (developmental code nameEMD-49980) is adopaminergic andserotonergicdrug which was originally developed by Merck KGaA for the treatment ofschizophrenia.[1][2][3] Inclinical trials itsantipsychotic efficacy was only modest but it was unexpectedly found to produce potent and rapidantidepressant andanxiolytic effects.[2][3] As a result, roxindole was further researched for the treatment ofdepression instead.[1][4] It has also been investigated as a therapy forParkinson's disease andprolactinoma.[5][6] However, it has never been marketed.[7]

Roxindole acts as anagonist at the followingreceptors:[8][9]

At D2 and possibly D3 receptors roxindole is apartial agonist with preferential actions atautoreceptors and has been touted as a 'selective' autoreceptor agonist, hence the justification of its application as an antipsychotic.[10][11] Weaker activity at the serotonin 1B and 1D receptors has been seen.[12] It is also aserotonin reuptake inhibitor (IC50 = 1.4 nM) and has been reported to act as a5-HT2A receptorantagonist as well.[9][10][11][13]

References

[edit]
  1. ^abGründer G, Wetzel H, Hammes E, Benkert O (1993). "Roxindole, a dopamine autoreceptor agonist, in the treatment of major depression".Psychopharmacology.111 (1):123–126.doi:10.1007/BF02257418.PMID 7870927.S2CID 8154586.
  2. ^abKlimke A, Klieser E (July 1991). "Antipsychotic efficacy of the dopaminergic autoreceptor agonist EMD 49980 (Roxindol). Results of an open clinical study".Pharmacopsychiatry.24 (4):107–112.doi:10.1055/s-2007-1014451.PMID 1684439.
  3. ^abKasper S, Fuger J, Zinner HJ, Bäuml J, Möller HJ (March 1992). "Early clinical results with the neuroleptic roxindole (EMD 49,980) in the treatment of schizophrenia--an open study".European Neuropsychopharmacology.2 (1):91–95.doi:10.1016/0924-977X(92)90041-6.PMID 1353388.S2CID 21861347.
  4. ^Maj J, Kolodziejczyk K, Rogóz Z, Skuza G (1996). "Roxindole, a potential antidepressant. I. Effect on the dopamine system".Journal of Neural Transmission.103 (5):627–641.doi:10.1007/bf01273159.PMID 8811507.S2CID 33701841.
  5. ^Bravi D, Davis TL, Mouradian MM, Chase TN (April 1993). "Treatment of Parkinson's disease with the partial dopamine agonist EMD 49980".Movement Disorders.8 (2):195–197.doi:10.1002/mds.870080214.PMID 8097280.S2CID 23676084.
  6. ^Jaspers C, Benker G, Reinwein D (June 1994). "Treatment of prolactinoma patients with the new non-ergot dopamine agonist roxindol: first results".The Clinical Investigator.72 (6):451–456.doi:10.1007/bf00180520.PMID 7950157.S2CID 532184.
  7. ^Elks, J. (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 1083.ISBN 978-1-4757-2085-3. Retrieved2 February 2025.
  8. ^Newman-Tancredi A, Cussac D, Audinot V, Millan MJ (June 1999)."Actions of roxindole at recombinant human dopamine D2, D3 and D4 and serotonin 5-HT1A, 5-HT1B and 5-HT1D receptors".Naunyn-Schmiedeberg's Archives of Pharmacology.359 (6):447–453.doi:10.1007/pl00005374.PMID 10431754.S2CID 19721911. Archived fromthe original on 2013-02-11.
  9. ^abHeinrich T, Böttcher H, Bartoszyk GD, Greiner HE, Seyfried CA, Van Amsterdam C (September 2004). "Indolebutylamines as selective 5-HT(1A) agonists".Journal of Medicinal Chemistry.47 (19):4677–4683.doi:10.1021/jm040792y.PMID 15341483.
  10. ^abSeyfried CA, Greiner HE, Haase AF (January 1989). "Biochemical and functional studies on EMD 49,980: a potent, selectively presynaptic D-2 dopamine agonist with actions on serotonin systems".European Journal of Pharmacology.160 (1):31–41.doi:10.1016/0014-2999(89)90651-1.PMID 2565817.
  11. ^abBartoszyk GD, Harting J, Minck KO (January 1996)."Roxindole: psychopharmacological profile of a dopamine D2 autoreceptor agonist".The Journal of Pharmacology and Experimental Therapeutics.276 (1):41–48.PMID 8558454.
  12. ^Newman-Tancredi A, Cussac D, Audinot V, Millan MJ (June 1999). "Actions of roxindole at recombinant human dopamine D2, D3 and D4 and serotonin 5-HT1A, 5-HT1B and 5-HT1D receptors".Naunyn-Schmiedeberg's Archives of Pharmacology.359 (6):447–453.doi:10.1007/pl00005374.PMID 10431754.S2CID 19721911.
  13. ^Maj J, Kołodziejczyk K, Rogóz Z, Skuza G (March 1997). "Roxindole, a dopamine autoreceptor agonist with a potential antidepressant activity. II. Effects on the 5-hydroxytryptamine system".Pharmacopsychiatry.30 (2):55–61.doi:10.1055/s-2007-979483.PMID 9131725.
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
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