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Milipertine

From Wikipedia, the free encyclopedia
Abandoned antipsychotic

Pharmaceutical compound
Milipertine
Clinical data
Other namesMillipertine; WIN18935; WIN-18,935; Win-18935
Identifiers
  • 5,6-dimethoxy-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2-methyl-1H-indole
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H31N3O3
Molar mass409.530 g·mol−1
3D model (JSmol)
  • CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4OC
  • InChI=1S/C24H31N3O3/c1-17-18(19-15-23(29-3)24(30-4)16-20(19)25-17)9-10-26-11-13-27(14-12-26)21-7-5-6-8-22(21)28-2/h5-8,15-16,25H,9-14H2,1-4H3
  • Key:XYAANYFFYIRFND-UHFFFAOYSA-N

Milipertine (INNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name; developmental code nameWIN-18935) is adrug described as anantipsychotic,neuroleptic, andtranquilizer which was under development for the treatment ofschizophrenia but was never marketed.[1][2][3][4]

Structurally, it is asubstituted tryptamine and a piperazinylethylindole.[5][6][7] The drug is closelystructurally related to other "pertines" includingalpertine,oxypertine, andsolypertine, which are also tryptamines and piperazinylethylindoles.[5][6][8]

The related drug oxypertine shows highaffinity for theserotonin5-HT2 anddopamineD2 receptors (Ki = 8.6 nM and 30 nM, respectively) and is also known to act as acatecholamine depleting agent.[9][10] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects oftryptamine, aserotonin receptoragonist, andapomorphine, adopamine receptoragonist, in animals.[9][11]ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be ametabolite of milipertine, as well as of oxypertine and several other drugs.[12][13]

Milipertine produced troublesomeside effects inclinical studies includingorthostatic hypotension,drowsiness,extrapyramidal symptoms,elevated liver enzymes, andweight loss.[14][15][4] The side effects of milipertine occurred too frequently and at doses well below those producing antipsychotic effects and its development was abandoned.[14][15][4]

Milipertine was first described in thescientific literature by 1968.[1]

See also

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References

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  1. ^abElks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 825.ISBN 978-1-4757-2085-3. Retrieved30 October 2024.
  2. ^Negwer M (1994).Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. p. 2306.ISBN 978-3-05-500156-7. Retrieved30 October 2024.
  3. ^Milne GW (2002).Drugs: Synonyms and Properties. Wiley. p. 429.ISBN 978-0-566-08491-1. Retrieved30 October 2024.
  4. ^abcMielke DH, Gallant DM, Bishop MP (June 1973). "Milipertine: an early evaluation in severely ill schizophrenics".Current Therapeutic Research, Clinical and Experimental.15 (6):324–326.PMID 4197256.
  5. ^abEllis GP, Luscombe DK (1996).Progress in Medicinal Chemistry. Elsevier Science. p. 219.ISBN 978-0-08-086281-1. Retrieved30 October 2024.Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles.
  6. ^abLednicer D, Mitscher LA (1980).The Organic Chemistry of Drug Synthesis, Volume 2. Organic Chemistry Series of Drug Synthesis. Wiley. pp. 341–343.ISBN 978-0-471-04392-8. Retrieved30 October 2024.
  7. ^Lednicer D (2009).Strategies for Organic Drug Synthesis and Design. Wiley. p. 390.ISBN 978-0-470-39959-0. Retrieved30 October 2024.
  8. ^Lajtha A (2013).Alterations of Metabolites in the Nervous System. Handbook of neurochemistry. Springer US. p. 335.ISBN 978-1-4757-6740-7. Retrieved30 October 2024.
  9. ^abMegens AA, Kennis LE (1996).Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?. Progress in Medicinal Chemistry. Vol. 33. pp. 185–232.doi:10.1016/s0079-6468(08)70306-0.ISBN 978-0-444-82310-6.PMID 8776944.
  10. ^Bak IJ, Hassler R, Kim JS (1969). "Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin".Zeitschrift für Zellforschung und Mikroskopische Anatomie.101 (3):448–462.doi:10.1007/BF00335580.PMID 5362847.S2CID 32583722.
  11. ^Niemegeers CJ, Janssen PA (June 1979). "A systematic study of the pharmacological activities of dopamine antagonists".Life Sciences.24 (24). Elsevier BV:2201–2216.doi:10.1016/0024-3205(79)90096-1.PMID 388130.
  12. ^Elliott S (2011). "Current awareness of piperazines: pharmacology and toxicology".Drug Testing and Analysis.3 (7–8):430–438.doi:10.1002/dta.307.PMID 21744514.Furthermore, oMeOPP is a metabolite of some prescribed drugs: enciprazione, milipertine, urapidil, dropropizine and oxypertine.[1,47]
  13. ^Caccia S, Notarnicola A, Fong MH, Benfenati E (January 1984). "Identification and quantitation of 1-arylpiperazines, metabolites resulting from side-chain cleavage of (4-substituted aryl-1-piperazinyl)alkyl heterocyclic derivatives in rat plasma and brain".Journal of Chromatography.283:211–221.doi:10.1016/s0021-9673(00)96256-3.PMID 6707118.
  14. ^abFDA Clinical Experience Abstracts. Food and Drug Administration. 1973. p. 1-PA15. Retrieved30 October 2024.
  15. ^abHeinzelman RV (1974).Annual Reports in Medicinal Chemistry. Academic Press. p. 3.ISBN 978-0-08-058353-2. Retrieved30 October 2024.
Tryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Triptans
Cyclized tryptamines
Isotryptamines
Related compounds
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