Ergometrine

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Ergometrine
Ergonovine-skeletal.svg Ergometrine3.png
Systematic (IUPAC) name
(6aR,9R)-N-((S)-1-Hydroxypropan- 2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Clinical data
AHFS/Drugs.com monograph
Pregnancy
category
  • X
Legal status
  • List I precursor (US)
Routes of
administration		 Oral
Pharmacokinetic data
Metabolism Liver
Excretion Kidney
Identifiers
CAS Number 60-79-7 YesY
ATC code G02AB03 (WHO)
PubChem CID: 443884
IUPHAR/BPS 148
DrugBank DB01253 YesY
ChemSpider 391970 YesY
UNII WH41D8433D YesY
KEGG D07905 YesY
ChEBI CHEBI:4822 YesY
ChEMBL CHEMBL119443 YesY
Synonyms Ergonovine, lysergic acid beta- propanolamide
Chemical data
Formula C19H23N3O2
Molecular mass 325.41 g/mol
  • O=C(N[C@@H](C)CO)[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C
  • 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 YesY
  • Key:WVVSZNPYNCNODU-XTQGRXLLSA-N YesY
  (verify)

Ergometrine also known as ergonovine or d-lysergic acid beta-propanolamide, is a medication use to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth.[1] It can be used either by mouth, by injection into a muscle, or injection into a vein. It begins working within 15 min when taken by mouth and is faster in onset when used by injection. Effects last between 45 and 180 minutes.[1]

Common side effect include high blood pressure, vomiting, seizures, headache, and low blood pressure. Other serious side effects include ergotism.[1] It was originally made from the rye ergot fungus but can also be made from lysergic acid.[2][3] Due to it being possible to made lysergic acid diethylamide (LSD) from ergometrine it is regulated.[4]

Ergometrine was discovered in 1932.[2] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[5] The wholesale cost is between 0.12 and 0.41 USD for an injectable dose and 0.01 USD for a pill as of 2014.[6][7] In the United States it is about 1.75 USD per dose.[1]

Medical use

It 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.[8] It is used to diagnose variant (Prinzmetal's) angina.[9]

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.[10] 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.[11] The drug is contraindicated in pregnancy, vascular disease, and psychosis.

Mechanism of action

While it acts at alpha-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.

History

The pharmacological properties of ergot were known and had been utilised by midwives for centuries, but were not thoroughly researched and publicised 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.[12]

Ergometrine was first isolated and obtained by the chemists C Moir and H W Dudley in 1935.[13] Caroline De Costa has argued that the adoption of ergometrine for prophylatic use and for treating haemorrhaging contributed to the decline in the maternal mortality rate in much of the West during the early 20th century.[12]

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.[14] 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.

See also

Methylergometrine - a synthetic analogue

References

  1. ↑ 1.0 1.1 1.2 1.3 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Ergometrine drug information
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ 12.0 12.1 Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ List Of Precursors And Chemicals Frequently Used In The Illicit Manufacture Of Narcotic Drugs And Psychotropic Substances Under International Control.
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