Chemistry:Ergometrine

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Short description: Lysergamide
Ergometrine
Ergonovine-skeletal.svg
Clinical data
Trade namesErgometrine Maleate, Ergonovine Maleate, Ergotrate, Ergotrate Maleate, Ergostat, Syntometrine, others[1][2]
Other namesErgonovine; d-Lysergic acid β-propanolamide
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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H23N3O2
Molar mass325.412 g·mol−1
3D model (JSmol)
  (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.[3][1] It can be used either by mouth, by injection into a muscle, or injection into a vein.[3] It begins working within 15 minutes when taken by mouth and is faster in onset when used by injection.[3] Effects last between 45 and 180 minutes.[3]

Common side effect include high blood pressure, vomiting, seizures, headache, and low blood pressure.[3] Other serious side effects include ergotism.[3] It was originally made from the rye ergot fungus but can also be made from lysergic acid.[4][5] Ergometrine is regulated because it can be used to make lysergic acid diethylamide (LSD).[6]

Ergometrine was discovered in 1932.[4] It is on the World Health Organization's List of Essential Medicines.[7][8]

Medical uses

Ergometrine has a medical use in obstetrics to facilitate delivery of the placenta and to prevent bleeding after childbirth by causing smooth muscle tissue in the blood vessel walls to narrow, thereby reducing blood flow. It is usually combined with oxytocin (Syntocinon) as syntometrine.

It can induce spasm of the coronary arteries.[9] It is used to diagnose variant (Prinzmetal's) angina.[10]

Side effects

Possible side effects include nausea, vomiting, abdominal pain, diarrhea, headache, dizziness, tinnitus, chest pain, palpitation, bradycardia, transient hypertension and other cardiac arrhythmias, dyspnea, rashes, and shock.[11] An overdose produces a characteristic poisoning, ergotism or "St. Anthony's fire": prolonged vasospasm resulting in gangrene and amputations; hallucinations and dementia; and abortions.

Gastrointestinal disturbances such as diarrhea, nausea, and vomiting, are common.[12] The drug is contraindicated in pregnancy, vascular disease, and psychosis.

Pharmacology

Pharmacodynamics

While ergometrine acts at α-adrenergic, dopaminergic, and serotonin receptors (the 5-HT2 receptor), it exerts on the uterus (and other smooth muscles) a powerful stimulant effect not clearly associated with a specific receptor type.[citation needed]

Ergometrine produces psychedelic effects at high doses (e.g., 2–10 mg; normal therapeutic doses are 0.2 to 0.4 mg).[13] This can be attributed to activation of 5-HT2A receptors.[14] Ergometrine is an agonist of the serotonin 5-HT2B receptor and has been associated with cardiac valvulopathy.[15]

History

The pharmacological properties of ergot were known and had been utilised by midwives for centuries, but were not thoroughly researched and publicized until the early 20th century. However, its abortifacient effects and the danger of ergotism meant that it was only prescribed cautiously, as in the treatment of postpartum haemorrhage.[16]

Ergometrine was first isolated and obtained by the chemists C Moir, H W Dudley and Gerald Rogers[citation needed] in 1935.[17][18] Caroline De Costa has argued that the adoption of ergometrine for preventative use and for treating bleeding contributed to the decline in the maternal mortality rate in much of the West during the early 20th century.[16]

Society and culture

Legal status

Ergometrine is listed as Table I precursors under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances, as possible precursor compound for LSD.[19] As an N-alkyl derivative of lysergamide, ergometrine is also covered by the Misuse of Drugs Act 1971, effectively rendering it illegal in the United Kingdom .

References

  1. ↑ 1.0 1.1 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 31 October 1999. pp. 113–. ISBN 978-0-7514-0499-9. https://books.google.com/books?id=mqaOMOtk61IC&pg=PA113. 
  2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 397–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA397. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Ergonovine Maleate". The American Society of Health-System Pharmacists. https://www.drugs.com/monograph/ergonovine-maleate.html. 
  4. ↑ 4.0 4.1 The evolution of drug discovery : from traditional medicines to modern drugs (1st ed.). Weinheim: Wiley-VCH. 2011. p. 245. ISBN 9783527326693. https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA245. 
  5. ↑ Drug Discovery: a History (Rev. and updated ed.). Chichester: Wiley. 2005. p. 349. ISBN 9780471899792. https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA349. 
  6. ↑ Forensic chemistry of substance misuse : a guide to drug control. Cambridge, UK: Royal Society of Chemistry. 2009. p. 190. ISBN 9780854041787. https://books.google.com/books?id=x9Z1QZ5NIEIC&pg=PA190. 
  7. ↑ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 
  8. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  9. ↑ "Images in cardiology: A coronary organic stenosis distal to severe, ergonovine induced spasm: decision making". Heart 91 (10): 1310. October 2005. doi:10.1136/hrt.2004.058560. PMID 16162623. 
  10. ↑ "Differences between coronary hyperresponsiveness to ergonovine and vasospastic angina". Japanese Heart Journal 41 (3): 257–268. May 2000. doi:10.1536/jhj.41.257. PMID 10987346. 
  11. ↑ "Ergometrine drug information". DrugsUpdate.com. http://www.drugsupdate.com/generic/view/138. 
  12. ↑ "Prophylactic ergometrine-oxytocin versus oxytocin for the third stage of labour". The Cochrane Database of Systematic Reviews 2004 (1): CD000201. 2004. doi:10.1002/14651858.CD000201.pub2. PMID 14973949. 
  13. ↑ "Entheogenic (hallucinogenic) effects of methylergonovine". Journal of Psychedelic Drugs 12 (2): 165–166. 1980. doi:10.1080/02791072.1980.10471568. PMID 7420432. 
  14. ↑ "Serotonin and serotonin receptors in hallucinogen action". Handbook of the Behavioral Neurobiology of Serotonin. Handbook of Behavioral Neuroscience. 31. 2020. pp. 843–863. doi:10.1016/B978-0-444-64125-0.00043-8. ISBN 9780444641250. 
  15. ↑ "Safety Pharmacology assessment of drugs with biased 5-HT(2B) receptor agonism mediating cardiac valvulopathy". Journal of Pharmacological and Toxicological Methods 69 (2): 150–161. 2014. doi:10.1016/j.vascn.2013.12.004. PMID 24361689. 
  16. ↑ 16.0 16.1 "St Anthony's fire and living ligatures: a short history of ergometrine". Lancet 359 (9319): 1768–1770. May 2002. doi:10.1016/S0140-6736(02)08658-0. PMID 12049883. 
  17. ↑ "The Substance Responsible for the Traditional Clinical Effect of Ergot". British Medical Journal 1 (3871): 520–523. March 1935. doi:10.1136/bmj.1.3871.520. PMID 20778930. 
  18. ↑ "Targeting the 5-HT system: Potential side effects". Neuropharmacology 179: 108233. November 2020. doi:10.1016/j.neuropharm.2020.108233. PMID 32805212. 
  19. ↑ "List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control". Vienna, Austria: International Narcotics Control Board. January 2007. http://www.incb.org/pdf/e/list/red.pdf. 

External links



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