Methysergide

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Methysergide
Methysergide chemical structure.svg
Systematic (IUPAC) name
(6aR,9R)-N-[(2S)-1-Hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
Clinical data
Trade names Deseril, Sansert
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a603022
Pregnancy
category
  • AU: C
  • US: X (Contraindicated)
Legal status
Identifiers
CAS Number 361-37-5 YesY
ATC code N02CA04 (WHO)
PubChem CID: 9681
IUPHAR/BPS 134
DrugBank DB00247 YesY
ChemSpider 9300 YesY
UNII XZA9HY6Z98 YesY
KEGG D02357 YesY
ChEMBL CHEMBL1065 YesY
Chemical data
Formula C21H27N3O2
Molecular mass 353.458 g/mol
  • 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 YesY
  • Key:KPJZHOPZRAFDTN-ZRGWGRIASA-N YesY
  (verify)

Methysergide (1-methyl-D-lysergic acid butanolamide or UML-491) is a prescription drug formerly used for prophylaxis of cluster headaches/migraine headaches, but is no longer recommended due to retroperitoneal/retropulmonary fibrosis.

Medical uses

Methysergide is used to treat headaches such as migraine and other recurrent throbbing headaches.[1] Methysergide is one of the most effective[2] medications for the prevention of migraine, but not for the treatment of an acute attack.

It is also used in carcinoid syndrome to treat severe diarrhea.[1] It may also be used in the treatment of serotonin syndrome.[3]

Side effects

It has a known side effect, retroperitoneal fibrosis,[4] which is severe, although uncommon. Other severe but uncommon side effects include pleural fibrosis, and subendocardial fibrosis.

In addition, there is an increased risk of left-sided cardiac valve dysfunction.[2][5][dead link]

Pharmacology

Methysergide interacts with serotonin (5-HT) receptors. Its therapeutic effect in migraine prophylaxis has been associated with its antagonism at the 5-HT2B receptor.[6] Furthermore, it is an antagonist at the 5-HT2C receptor, while at the 5-HT1A receptor it serves as a partial agonist.[7][8][9] It is known to have partial agonist effects on some of the other 5-HT receptors as well.[10] Methysergide is metabolised into methylergometrine in humans, which is responsible for its psychedelic effects.[11]

History

Methysergide was approved by the U.S. Food and Drug Administration (FDA) in 1962.

Novartis withdrew it from the U.S. market after taking over Sandoz, but currently lists it as a product.[citation needed]

See also

References

  1. ↑ 1.0 1.1 http://tranquilene.com/methysergide.html
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ emedicine.com (2002)
  5. ↑ 1997 Mayo Clinic study linking heart disease to Fen Phen Valvular heart disease associated with fenfluramine-phentermine
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found. Page 187
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9681
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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