Methylergometrine

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Methylergometrine
Methylergometrin.svg
Systematic (IUPAC) name
9,10-Didehydro-N-[1-(hydroxymethyl)-propyl]-D-lysergamide
Clinical data
Trade names Methergine
AHFS/Drugs.com International Drug Names
MedlinePlus a601077
Pregnancy cat. Contraindicated
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Metabolism Liver
Half-life 30–120 min
Excretion Mostly bile
Identifiers
CAS number 113-42-8 YesY
ATC code G02AB01
PubChem CID 8226
ChemSpider 7933 N
UNII W53L6FE61V N
ChEMBL CHEMBL1201356 N
Synonyms Methylergobasine
Methylergobrevin
Methylergonovine
Chemical data
Formula C20H25N3O2 
Mol. mass 339.432 g/mol
Physical data
Melt. point 172 °C (342 °F)
Solubility in water insoluble mg/mL (20 °C)
 N (what is this?)  (verify)

Methylergometrine (other names include methylergonovine, methylergobasin, methergine, and D-lysergic acid 1-butanolamide) is a synthetic analogue of ergonovine, a psychedelic alkaloid found in ergot, and many species of morning glory. It is a member of the ergoline family and chemically similar to LSD, ergine, ergometrine, and lysergic acid. Due to its oxytocic properties, it has a medical use in obstetrics. According to Jonathan Ott, methylergonovine has LSD-like actions above 2 milligrams[citation needed]. Clinical dosages are ten times lower.

Methylergometrine maleate is marketed under the trade name Methergine.

Uses[edit]

Obstetric use[edit]

Methylergometrine is a smooth muscle constrictor that mostly acts on the uterus. It is most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion, and also to aid in expulsion of retained products of conception after a missed abortion (miscarriage in which all or part of the fetus remains in the uterus) and to help deliver the placenta after childbirth. It is available as tablets or injection (IM or IV) or in liquid form to be taken orally.[1][2][3]

Migraine[edit]

Methylergometrine is sometimes used for both prevention[4] and acute treatment[5] of migraine. It is an active metabolite of methysergide.

Contraindications[edit]

Methylergometrine is contraindicated in patients with hypertension and preeclampsia, and also during pregnancy and birth.[1]

Side effects[edit]

Adverse effects include:[1]

  • Cholinergic effects such as nausea, vomiting, and diarrhea
  • Dizziness
  • Pulmonary hypertension[citation needed]
  • Coronary artery vasoconstriction
  • Severe systemic hypertension (especially in patients with preeclampsia)
  • Convulsions

In excessive doses, methylergometrine can also lead to cramping, respiratory depression and coma.[1]

Interactions[edit]

Methylergometrine likely interacts with drugs that inhibit the liver enzyme CYP3A4, such as azole antifungals, macrolide antibiotics and many HIV drugs. It can also increase constriction of blood vessels caused by sympathomimetic drugs and other ergot alkaloids.[1]

Mechanism of action[edit]

Methylergometrine is a partial agonist/antagonist on serotonergic, dopaminergic and alpha-adrenergic receptors. Its specific binding and activation pattern on these receptors leads to a highly, if not completely, specific contraction of smooth uterus muscle via 5-HT2A serotonin receptors,[6] while blood vessels are affected to a lesser extent compared to other ergot alkaloids.[1]

References[edit]

  1. ^ a b c d e f Jasek, W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 5193–5. ISBN 978-3-85200-181-4. 
  2. ^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 447. ISBN 3-8047-1763-2. 
  3. ^ Fachinformation des Arzneimittel-Kompendium der Schweiz: Methergin (German)
  4. ^ Koehler, PJ; Tfelt-Hansen PC (Nov 2008). "History of methysergide in migraine.". Cephalalgia 28 (11). doi:10.1111/j.1468-2982.2008.01648.x. PMID 18644039. Retrieved 11 December 2011. 
  5. ^ Niño-Maldonado, Alfredo; Gary Caballero-García; Wilfrido Mercado-Bochero; Fernando Rico-Villademoros; Elena P Calandre (8 Nov 2009). "Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study". Head Face Med 5 (21). doi:10.1186/1746-160X-5-21. PMC 2780385. PMID 19895705. 
  6. ^ Heinz Pertz, Eckart Eich (1999). "Ergot alkaloids and their derivatives as ligands for serotoninergic, dopaminergic and adrenergic receptors". In Vladimír Křen,Ladislav Cvak. Ergot: the genus Claviceps. CRC Press. pp. 411–440. ISBN 978-905702375-0.