Methysergide

Methysergide
Clinical data
Trade namesDesernil, Sansert
Other namesUML-491; 1-Methylmethylergonovine; N-[(2S)-1-Hydroxybutan-2-yl]-1,6-dimethyl-9,10-didehydroergoline-8α-carboxamide; N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide
AHFS/Drugs.comInternational Drug Names
MedlinePlusa603022
Pregnancy
category
  • AU: C
ATC code
Legal status
Legal status
Identifiers
  • (6aR,9R)-N-[(2S)-1-Hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.041 Edit this at Wikidata
Chemical and physical data
FormulaC21H27N3O2
Molar mass353.466 g·mol−1
3D model (JSmol)
  • O=C(N[C@@H](CC)CO)[C@@H]3/C=C2/c4cccc1c4c(cn1C)C[C@H]2N(C3)C
  • InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15+,19-/m1/s1 checkY
  • Key:KPJZHOPZRAFDTN-ZRGWGRIASA-N checkY
  (verify)

Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches.[2] It has been withdrawn from the market in the United States and Canada due to safety concerns.[3] It is taken by mouth.[3]

The drug is a prodrug of methylergometrine (methylergonovine),[4] which circulates at levels about 10 times higher than those of methysergide during treatment with methysergide.[5][6][4] Whereas methysergide is a mixed agonist of some serotonin receptors (e.g., the 5-HT1 receptors) and antagonist of other serotonin receptors (e.g., the 5-HT2 receptors), methylergonovine is a non-selective agonist of most of the serotonin receptors, including of both the serotonin 5-HT1 and 5-HT2 receptor subgroups.[7] Methysergide and methylergometrine are ergolines and lysergamides and are related to the ergot alkaloids.[8]

Methysergide was first described in the literature by 1958.[9][10] It is no longer recommended as a first-line therapy for migraines or cluster headaches. This is due to toxicity, such as cardiac valvulopathy, which was first reported with long-term use in the late 1960s. Ergot-based medications like methysergide fell out of favor for treatment of migraine with the introduction of the triptans in the 1980s.

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 677–. ISBN 978-3-88763-075-1.
  3. ^ a b Cite error: The named reference pmid23815106 was invoked but never defined (see the help page).
  4. ^ a b Cite error: The named reference Leff1998 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference MajrashiRamesh2017 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference pmid11104741 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference GuzmanArmer2020 was invoked but never defined (see the help page).
  8. ^ Keller U, Tudzynski P (2002). "Ergot Alkaloids". Industrial Applications. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 157–181. doi:10.1007/978-3-662-10378-4_8. ISBN 978-3-642-07481-3.
  9. ^ Doepfner W, Cerletti A (1958). "Comparison of lysergic acid derivatives and antihistamines as inhibitors of the edema provoked in the rat's paw by serotonin". Int Arch Allergy Appl Immunol. 12 (1–2): 89–97. doi:10.1159/000228445. PMID 13549054.
  10. ^ Sicuteri F (1959). "Prophylactic and therapeutic properties of 1-methyl-lysergic acid butanolamide in migraine". Int Arch Allergy Appl Immunol. 15 (4–5): 300–307. doi:10.1159/000229055. PMID 14446408.