Methysergid

Strukturformel
Strukturformel von Methysergid
Allgemeines
Freiname Methysergid
Andere Namen

1-Methyl-D-lysergsäure-(1-hydroxybut-2-yl)amid (IUPAC)

Summenformel C21H27N3O2
Kurzbeschreibung

farbloser bis gelblicher Feststoff (Maleat-Salz)[1]

Externe Identifikatoren/Datenbanken
CAS-Nummer
EG-Nummer 206-644-0
ECHA-InfoCard 100.006.041
PubChem 9681
ChemSpider 9300
DrugBank DB00247
Wikidata Q424442
Arzneistoffangaben
ATC-Code

N02CA04

Eigenschaften
Molare Masse 353,46 g·mol−1
Aggregatzustand

fest

Schmelzpunkt

194–196 °C[2]

Löslichkeit
  • 2 mg·ml−1 in Wasser (Maleat)[1]
  • > 10 mg·ml−1 in DMSO (Maleat)[1]
  • > 20 mg·ml−1 in Methanol (Maleat)[1]
Sicherheitshinweise
Bitte die Befreiung von der Kennzeichnungspflicht für Arzneimittel, Medizinprodukte, Kosmetika, Lebensmittel und Futtermittel beachten
GHS-Gefahrstoffkennzeichnung[1]

Gefahr

H- und P-Sätze H: 301
P: 301+310[1]
Toxikologische Daten

440 mg·kg−1 (LD50Mausoral)[2]

Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Methysergid ist ein Arzneistoff aus der Gruppe der Lysergsäureamide, der in der vorbeugenden Behandlung der Migräne eingesetzt wurde. Er wirkt als Antagonist oder Partialagonist an verschiedenen Serotoninrezeptoren (5-HT-Rezeptoren). Seine migräneprophylaktische Wirkung wurde insbesondere mit einer Hemmung von 5-HT2B in Verbindung gebracht.[3] Auf Grund schwerer Nebenwirkungen, insbesondere Retroperitonealfibrosen, Pleuralfibrosen, Pleuraerguss[4] und Herzklappenfibrosen, wurde Methysergid vom Markt genommen.[5]

Einzelnachweise

  1. a b c d e f Datenblatt Methysergide maleate salt bei Sigma-Aldrich, abgerufen am 12. Mai 2017 (PDF).
  2. a b Eintrag zu Methysergid. In: Römpp Online. Georg Thieme Verlag, abgerufen am 29. Dezember 2014.
  3. Schmuck K, Ullmer C, Kalkman HO, Probst A, Lubbert H: Activation of meningeal 5-HT2B receptors: an early step in the generation of migraine headache? In: Eur. J. Neurosci. 8. Jahrgang, Nr. 5, Mai 1996, S. 959–967, PMID 8743744.
  4. Berthold Jany, Tobias Welte: Pleuraerguss des Erwachsenen – Ursachen, Diagnostik und Therapie. In: Deutsches Ärzteblatt. Band 116, Nr. 21, (Mai) 2019, S. 377–385, hier: S. 380.
  5. Koehler PJ, Tfelt-Hansen PC: History of methysergide in migraine. In: Cephalalgia. 28. Jahrgang, Nr. 11, November 2008, S. 1126–1135, doi:10.1111/j.1468-2982.2008.01648.x, PMID 18644039.

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