methysergide   Click here for help

GtoPdb Ligand ID: 134

Synonyms: 1-methylmethylergonovine | Deseril® | Sansert® | UML-491
Approved drug PDB Ligand
methysergide is an approved drug (FDA (1962))
Compound class: Synthetic organic
Comment: Methysergide is an ergot alkaloid. When used, this drug is administered as methysergide maleate (PubChem CID 5281073). The use of ergot alkaloids has been discontinued or restricted due to their propensity to cause fibrosis.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 57.5
Molecular weight 353.21
XLogP 1.84
No. Lipinski's rules broken 0
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Canonical SMILES CCC(NC(=O)C1CN(C)C2C(=C1)c1cccc3c1c(C2)cn3C)CO
Isomeric SMILES CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3C)CO
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
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Summary of Clinical Use Click here for help
Used in the treatment of migraine and cluster headaches. Use of this drug is discontinued in the US.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Serotonin receptor antagonist acting on the central nervous system leading to smooth muscle constriction.