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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

Obstetric use

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

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

Contraindications

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

Side effects

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

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

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-HT_2A serotonin receptors,^[6] while blood vessels are affected to a lesser extent compared to other ergot alkaloids.^[1]

References

^ ^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.
^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 447. ISBN 3-8047-1763-2.
^ Fachinformation des Arzneimittel-Kompendium der Schweiz: Methergin (German)
^ Koehler, PJ; Tfelt-Hansen PC (Nov 2008). "History of methysergide in migraine.". Cephalalgia 28 (11): 1126–35. doi:10.1111/j.1468-2982.2008.01648.x. PMID 18644039. Retrieved 11 December 2011.
^ 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.
^ 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.

UpToDate Contents

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1. 経膣分娩後遺残胎盤 retained placenta after vaginal birth
2. 群発頭痛：治療および予後 cluster headache treatment and prognosis

English Journal

A sensitive LC-MS/MS method to quantify methylergonovine in human plasma and its application to a pharmacokinetic study.

Gao Y1, Sun Q2, Liu D2, Ma B3, Zhao H4, Fang Z4, Wang H4, Lou H5.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2015 Dec 28;1011:62-68. doi: 10.1016/j.jchromb.2015.12.046. [Epub ahead of print]
Methylergonovine (ME) is a semisynthetic ergot alkaloid that is used for the treatment and prophylaxis of postpartum hemorrhage. In recent years, methylergonovine has been effective in the control of refractory headaches and is likely to be employed as chemosensitizers for cancer. However, this alka
PMID 26760224

[Dobutamine-related coronary spasm among patients with false positive dobutamine stress echocardiography: Prevalence and predictors].

Aboukhoudir F1, Aboukhoudir I2, Pansieri M2, Rekik S3.
Annales de cardiologie et d'angéiologie.Ann Cardiol Angeiol (Paris).2015 Nov;64(5):313-7. doi: 10.1016/j.ancard.2015.09.027. Epub 2015 Oct 21.
BACKGROUND AND OBJECTIVE: Dobutamine stress echocardiography (DSE) is being consistently used as an exercise-independent stress modality aimed at the detection of coronary artery disease (CAD) and the evaluation of myocardial ischemia. It may though occasionally induce coronary vasospasm. In this st
PMID 26499214

The Effect of the Combined Use of Methylergonovine and Oxytocin during Caesarean Section in the Prevention of Postpartum Haemorrhage.

Şentürk Ş1, Kağıtçı M1, Balık G1, Arslan H1, Kır Şahin F1.
Basic & clinical pharmacology & toxicology.Basic Clin Pharmacol Toxicol.2015 Oct 9. doi: 10.1111/bcpt.12500. [Epub ahead of print]
We aimed to show the benefit to patients of postpartum hemorrhage prophylaxis treatment and the effectiveness as a uterotonic agent of the combined use of methylergonovine and oxytocin infusion in the prevention of hemorrhage during and after caesarean section, by comparison with a control group whi
PMID 26449959

Japanese Journal

Reversible cerebral vasoconstriction syndrome with limb myoclonus following intravenous administration of methylergometrine

ISHIBASHI Tomoko,ISHIBASHI Satoru,UCHIDA Tokujiro,NAKAZAWA Koichi,MAKITA Koshi
Journal of anesthesia 25(3), 405-408, 2011-06-20
NAID 10029023187

マレイン酸メチルエルゴメトリンによる肺胞出血の1例

磯部和順,岩田基秀,石田文昭,鏑木教平,後町杏子,村松陽子,阪口真之,佐藤大輔,佐野剛,草野英美子,坂本晋,高井雄二郎,渋谷和俊,本間栄
日本呼吸器学会雑誌 = The journal of the Japanese Respiratory Society 46(12), 1007-1012, 2008-12-10
NAID 10024823049

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リンク元	「メチルエルゴメトリン」「メチルエルゴノビン」
拡張検索	「methylergometrine maleate」

「メチルエルゴメトリン」

Methylergometrine
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
ATC code	G02AB01
PubChem	CID 8226
ChemSpider	7933
UNII	W53L6FE61V
ChEMBL	CHEMBL1201356
Synonyms	Methylergobasine; Methylergobrevin; Methylergonovine
Chemical data
Formula	C20H25N3O2
Molecular mass	339.432 g/mol
	SMILES CC[C@@H](CO)NC(=O)[C@@H]2/C=C1/c3cccc4N\C=C(\C[C@H]1N(C)C2)c34;
	InChI InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1 ; Key:UNBRKDKAWYKMIV-QWQRMKEZSA-N ;
Physical data
Melting point	172 °C (342 °F)
Solubility in water	insoluble mg/mL (20 °C)
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