Ergometrine

Ergometrine
Clinical data
Trade namesErgometrine Maleate, Ergonovine Maleate, Ergotrate, Ergotrate Maleate, Ergostat, Syntometrine, others[1][2]
Other namesergonovine[3]; ᴅ-lysergic acid β-propanolamide[4]; ᴅ-lysergic acid α-hydroxymethylethylamide[4]; ᴅ-(+)-lysergic acid-β-hydroxyisopropylamide[4]
AHFS/Drugs.comMonograph
Pregnancy
category
  • X
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver (partly CYP3A4)
Elimination half-life2-phase (10 min; 2 hrs)
ExcretionBiliary
Identifiers
  • (6aR,9R)-N-((S)-1-Hydroxypropan- 2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.441 Edit this at Wikidata
Chemical and physical data
FormulaC19H23N3O2
Molar mass325.412 g·mol−1
3D model (JSmol)
  • [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@@H](C(=O)N[C@@H](C)CO)CN2C)c34
  • InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1 checkY
  • Key:WVVSZNPYNCNODU-XTQGRXLLSA-N checkY
  (verify)

Ergometrine, also known as ergonovine and sold under the brand names Ergotrate, Ergostat, and Syntometrine among others, is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth.[6][1] It can be used either by mouth, by injection into a muscle, or injection into a vein.[6] It begins working within 15 minutes when taken by mouth and is faster in onset when used by injection.[6] Effects last between 45 and 180 minutes.[6]

Common side effect include high blood pressure, vomiting, seizures, headache, and low blood pressure.[6] Other serious side effects include ergotism.[6] It was originally made from the rye ergot fungus but can also be made from lysergic acid.[7][8] Ergometrine is regulated because it can be used to make lysergic acid diethylamide (LSD).[9]

Ergometrine was discovered in 1932.[7] It is on the World Health Organization's List of Essential Medicines.[10][11]

  1. ^ a b Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 113–. ISBN 978-0-7514-0499-9.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 397–. ISBN 978-3-88763-075-1.
  3. ^ International Narcotics Control Board Red List, 17ᵗʰ edition, January 2020 (PDF). Vienna International Centre, P.O. Box 500, 1400 Vienna, Austria: International Narcotics Control Board. p. 11. Retrieved 2024-11-17.{{cite book}}: CS1 maint: location (link)
  4. ^ a b c International Narcotics Control Board Red List, 17ᵗʰ edition, January 2020 (PDF). Vienna International Centre, P.O. Box 500, 1400 Vienna, Austria: International Narcotics Control Board. p. 13. Retrieved 2024-11-17.{{cite book}}: CS1 maint: location (link)
  5. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  6. ^ a b c d e f "Ergonovine Maleate". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-25. Retrieved 1 December 2015.
  7. ^ a b Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1st ed.). Weinheim: Wiley-VCH. p. 245. ISBN 9783527326693. Archived from the original on 2015-12-26.
  8. ^ Sneader W (2005). Drug Discovery: a History (Rev. and updated ed.). Chichester: Wiley. p. 349. ISBN 9780471899792. Archived from the original on 2015-12-26.
  9. ^ King LA (2009). Forensic chemistry of substance misuse : a guide to drug control. Cambridge, UK: Royal Society of Chemistry. p. 190. ISBN 9780854041787. Archived from the original on 2015-12-26.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.