ergometrine

Also known as Ergotrate®, Methergine®, N-(2-Hydroxy-1-methylethyl)-D-(+)-lysergamide, D-lysergic acid 1-hydroxymethylethylamide, D-lysergic acid-L-propanolamide, [8beta(S)]-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide, 9,10-didehydro-N-(alpha-(hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamide, N-(alpha-(hydroxymethyl)ethyl)-D-lysergamide

Ergonovine, also known as ergometrine and lysergic acid propanolamide, is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth. It can be used either by mouth, by injection into a muscle, or injection into a vein.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 443732517
Drug.image: Ergonovine-skeletal.svg
Drug.image_class: skin-invert-image
Drug.width: 200px
Drug.image2: Ergonovine 3D.png
Drug.image_class2: bg-transparent
Drug.width2: 200px
Drug.tradename: Ergotrate, Ergotrate Maleate
Drug.routes_of_administration: oral, intramuscular, intravenous
Drug.class: Serotonin receptor agonists; Uterotonic
Drug.ATC_prefix: G02
Drug.ATC_suffix: AB03
Drug.legal_BR: D1
Drug.legal_CA: Schedule VI
Drug.legal_US: Rx only
Drug.elimination_half life: 2-phase (10 min; 2 hrs)
Drug.metabolism: Liver (partly CYP3A4)

via Wikipedia infobox

Chemical data

Formula: C19H23N3O2
Molecular weight: 325.4 g/mol
IUPAC name: (6aR,9R)-N-[(2S)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
SMILES: C[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChIKey: WVVSZNPYNCNODU-XTQGRXLLSA-N
XLogP: 1.8
Polar surface area: 68.4 Å²
H-bond donors: 3
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

2,845 papers

Ergometrine.Journal of obstetrics and gynaecology : the journal of the Institute of Obstetrics and Gynaecology · 2005
Ergometrine.British medical journal · 1970
Prophylactic ergometrine-oxytocin versus oxytocin for the third stage of labour.The Cochrane database of systematic reviews · 2004
Ergometrine stability in postpartum haemorrhage kits: Does temperature and light matter?The Australian & New Zealand journal of obstetrics & gynaecology · 2020
Ergometrine-induced atrial fibrillation at caesarean section.BMJ case reports · 2019

via PubMed

Wikidata facts

Mass: 325.179027

Show 5 more facts

chemical formula: C₁₉H₂₃N₃O₂
World Health Organisation international non-proprietary name: ergometrine
isomeric SMILES: C[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
canonical SMILES: CC(CO)NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C
defined daily dose: 0.2

Sources (4)

via Wikidata · CC0

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