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Propisergide

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Pharmaceutical compound
Propisergide
Clinical data
Other namesPML-946; PML946; Ergalgin;N-Methylergobasine;N-Methylergonovine;N-Methylergometrine; 1-Methylergonovine
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator;Antimigraine agent
ATC code
  • None
Identifiers
  • (6aR,9R)-N-[(2S)-1-hydroxypropan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H25N3O2
Molar mass339.439 g·mol−1
3D model (JSmol)
  • C[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C
  • InChI=1S/C20H25N3O2/c1-12(11-24)21-20(25)14-7-16-15-5-4-6-17-19(15)13(9-22(17)2)8-18(16)23(3)10-14/h4-7,9,12,14,18,24H,8,10-11H2,1-3H3,(H,21,25)/t12-,14+,18+/m0/s1
  • Key:XUKAVPATXGYVKJ-WPKBUWHJSA-N

Propisergide (INNTooltip International Nonproprietary Name; developmental code namePML-946), also known asergalgin or asN-methylergometrine or1-methylergometrine, is aserotonin receptormodulator andantimigraine agent of theergoline andlysergamide families which was never marketed.[2][3][4][5][6] It is the 1-methylderivative ofergometrine (ergonovine) and is a closeanalogue ofmethylergonovine andmethysergide (UML-491).[7][5][8] Extensivemetabolism of other 1-methylated lysergamides to theirsecondary aminederivatives, for instancemethysergide (1-methylmethylergometrine) conversion intomethylergometrine, has been observed.[9][10] Propisergide has 259% of theantiserotonergic activity of LSD.[7][1] Its average clinical dose range forpreventative treatment of migraine is 1 to 3 mgorally.[1] Propisergide was first described in the literature by 1958[7][11] and then further around 1980 and after.[6][12][13]

See also

[edit]

References

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  1. ^abcSicuteri F (October 1963). "Prophylactic Treatment of Migraine by Means of Lysergic Acid Derivatives".Triangle.6:116–125.PMID 14087164.
  2. ^Elks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US.ISBN 978-1-4757-2085-3. Retrieved13 March 2025.
  3. ^Ganellin CR, Triggle DJ (1996).Dictionary of Pharmacological Agents. Taylor & Francis.ISBN 978-0-412-46630-4. Retrieved13 March 2025.
  4. ^Waldman M, Fraczkiewicz R, Clark RD (September 2015). "Tales from the war on error: the art and science of curating QSAR data".Journal of Computer-Aided Molecular Design.29 (9):897–910.Bibcode:2015JCAMD..29..897W.doi:10.1007/s10822-015-9865-0.PMID 26290258.
  5. ^abGelfand MD, West GB (1961). "Experimental studies with the butanolamide and propanolamide of 1-methyl-lysergic acid".Int Arch Allergy Appl Immunol.18:286–291.doi:10.1159/000229179.PMID 13704268.
  6. ^abOelszner W (1980). "Displacement of specific serotonin and lysergic acid diethylamide binding by Ergalgin, a new antiserotonin drug".Acta Biologica et Medica Germanica.39 (8–9):897–901.PMID 7282219.
  7. ^abcDoepfner W, Cerletti A (1958). "Comparison of lysergic acid derivatives and antihistamines as inhibitors of the edema provoked in the rat's paw by serotonin".International Archives of Allergy and Applied Immunology.12 (1–2):89–97.doi:10.1159/000228445.PMID 13549054.
  8. ^"Propisergide".PubChem. U.S. National Library of Medicine. Retrieved13 March 2025.
  9. ^Majrashi M, Ramesh S, Deruiter J, Mulabagal V, Pondugula S, Clark R, et al. (2017). "Multipotent and Poly-therapeutic Fungal Alkaloids of Claviceps purpurea". In Agrawal DC, Tsay HS, Shyur LF, Wu YC, Wang SY (eds.).Medicinal Plants and Fungi: Recent Advances in Research and Development. Medicinal and Aromatic Plants of the World. Vol. 4. pp. 229–252.doi:10.1007/978-981-10-5978-0_8.ISBN 978-981-10-5977-3.ISSN 2352-6831.Metabolites of methysergide also exhibit pharmacological activity. Methylergometrine (one of methysergide's metabolites) is responsible for methysergide's therapeutic effects regarding migraine treatment (Müller-Schweinitzer and Tapparelli 1986). [...] The systemic availability of methysergide after oral administration is only 13%, due to a high degree of first-pass metabolism by N-1 demethylation to methylergometrine. After oral administration, the plasma concentrations of the metabolite are considerably higher than those of the parent drug, and the area under the plasma concentration curve (AUC) for methylergometrine is more than ten times greater than for methysergide.
  10. ^Müller-Schweinitzer E, Tapparelli C (March 1986). "Methylergometrine, an active metabolite of methysergide".Cephalalgia.6 (1):35–41.doi:10.1046/j.1468-2982.1986.0601035.x.PMID 3698092.S2CID 5778173.
  11. ^World Health Organization (1962).Cumulative List of Proposed International Non-proprietary Names for Pharmaceutical Preparations. 1962-. World Health Organization.ISBN 978-92-4-056013-0. Retrieved13 March 2025.{{cite book}}:ISBN / Date incompatibility (help)
  12. ^Bartsch R, Nowak R (January 1979). "Pharmacological Evaluation of a New Ergolin Derivative (Ergalgin)".Die Pharmazie.34 (5–6). Eschborn, Germany: Govi-Verlag Pharmazeutischer GmbH: 358.
  13. ^Harhammer R, Morgenstern R, Ott T (1992). "Pharmacological Effects of Ergalgin, a Potent Antagonist at Central and Peripheral 5-Ht (2) Receptors".Biogenic Amines.8 (3–4):267–275.
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
Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources
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