Methysergide

Methysergide

Clinical data
Trade names	Deseril, Sansert
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a603022
Pregnancy category	AU: C US: X (Contraindicated)
ATC code	N02CA04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Identifiers
IUPAC name (6aR,9R)-N-[(2S)-1-Hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number	361-37-5 Y
PubChem (CID)	9681
IUPHAR/BPS	134
DrugBank	DB00247 Y
ChemSpider	9300 Y
UNII	XZA9HY6Z98 Y
KEGG	D02357 Y
ChEMBL	CHEMBL1065 Y
ECHA InfoCard	100.006.041
Chemical and physical data
Formula	C21H27N3O2
Molar mass	353.458 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N[C@@H](CC)CO)[C@@H]3/C=C2/c4cccc1c4c(cn1C)C[C@H]2N(C3)C
InChI 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 Y Key:KPJZHOPZRAFDTN-ZRGWGRIASA-N Y

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.

Methysergide is used to treat headaches such as migraine and other recurrent throbbing headaches. Methysergide is one of the most effective 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. It may also be used in the treatment of serotonin syndrome.

It has a known side effect, retroperitoneal fibrosis, 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.

Methysergide interacts with serotonin (5-HT) receptors. Its therapeutic effect in migraine prophylaxis has been associated with its antagonism at the 5-HT_2B receptor. Furthermore, it is an antagonist at the 5-HT_2C receptor, while at the 5-HT_1A receptor it serves as a partial agonist. It is known to have partial agonist effects on some of the other 5-HT receptors as well. Methysergide is metabolised into methylergometrine in humans, which is responsible for its psychedelic effects.