methylergonovine   Click here for help

GtoPdb Ligand ID: 150

Synonyms: Methergine® | methylergobasin
Approved drug PDB Ligand
methylergonovine is an approved drug (FDA (1946))
Compound class: Synthetic organic
Comment: Methylergonovine is a synthetic analogue of the natural ergot alkaloid, ergometrine. It acts through interaction with multiple molecular targets, including adrenoceptors, dopamine receptors, and 5-HT receptors.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 68.36
Molecular weight 339.19
XLogP 1.54
No. Lipinski's rules broken 0
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Canonical SMILES CCC(NC(=O)C1CN(C)C2C(=C1)c1cccc3c1c(C2)c[nH]3)CO
Isomeric SMILES CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CO
InChI InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1
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Summary of Clinical Use Click here for help
Used in the prevention of excessive bleeding after childbirth.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug appears to have multiple molecular targets, including adrenoceptors, dopamine receptors, and 5-HT receptors, although the exact mechanism of action remains unclear. Through antagonism of the dopamine D1 receptor in the smooth muscle of the uterus methylergonovine increases the tone, rate and amplitude of contractions which leads to the third stage of labour being shortened and blood loss being reduced.