methysergide
Trade name: sansert
Approved
Feb 12, 1962
Methysergide is an oral, synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD. Methysergide is used prophylactically to reduce the frequency and intensity of severe vascular headaches. Although methysergide is an ergot alkaloid, it is a weak vasoconstrictor and oxytocic. Methysergide is a more potent antagonist of peripheral serotonin receptors than other ergot alkaloids. Methysergide is not just a 5HT2 antagonist, it is also a 5HT1 agonist. Although methysergide and sumatriptan both stimulate serotonin receptors centrally, methysergide is intended for prophylaxis while sumatriptan is indicated for treatment of an acute attack. Methysergide was approved by the FDA in 1962. Methysergide was formerly used for prophylaxis of cluster headaches/migraine headaches, but is no longer recommended due to retroperitoneal/retropulmonary fibrosis. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 1 marketing orgs
Timeline
Indications
Approved for
Mechanism of action
- Serotonin 2b (5-HT2b) receptorANTAGONIST
HTR2B antagonist
- Serotonin 2c (5-HT2c) receptorANTAGONIST
HTR2C antagonist
- Serotonin 1a (5-HT1a) receptorPARTIAL AGONIST
HTR1A partial agonist
Approval history
- approvedPriority reviewFeb 12, 1962
Chemistry & pharmacology
SMILES
CC[C@@H](CO)NC(=O)[C@@H]1C=C2c3cccc4c3c(cn4C)C[C@H]2N(C)C1- Mol. weight
- 353.47 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Discontinued
Oral
Yes
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL1065 ↗
- WikipediaMethysergide ↗
- NCATSXZA9HY6Z98 ↗
- ChEMBLCHEMBL485253 ↗
- ChEMBLCHEMBL3989558 ↗
- ChEMBLCHEMBL1200938 ↗
Also known as
- 1-methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide
- 1-methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide
- 1-methyl-d-lysergic acid butanolamide
- 1-methyl-d-lysergic acid butanolamide
- 1-methyl-d-lysergic acid butanolamide
- 1-methyllysergic acid butanolamide
- 1-methyllysergic acid butanolamide
- 1-methyllysergic acid butanolamide
- 1-methyllysergic acid butanolamide tartrate, (r-(r*,r*))-(8beta)-isomer
- 1-methylmethylergonovine
- 1-methylmethylergonovine
- (+)-9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide
- (+)-9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide
- 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide
- 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide
- deseril
- deseril
- deseril
- deseril
- deseril
- deseril
- methysergid
- methysergide
- methysergide
- methysergide
- methysergide
- methysergide
- methysergide
- methysergide
- methysergide maleate
- methysergide maleate
- methysergide maleate
- methysergide maleate
- methysergidum
- methysergidum
- metisergida
- metisergida
- metisergido
- metisergido
- n-(1-(hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
- n-(1-(hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
- (+)-n-(1-(hydroxymethyl)propyl)-1-methyl-d-lysergamide
- (+)-n-(1-(hydroxymethyl)propyl)-1-methyl-d-lysergamide
- sansert
- sansert
- sansert