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a salt or ester of maleic acid; used as a nontricyclic antidepressant drug for psychomotor activation

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/16 22:17:39」(JST)

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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. 経腟分娩後の出血管理 management of postpartum hemorrhage at vaginal delivery
2. 産後出血の概要 overview of postpartum hemorrhage
3. 分娩第3期のマネージメントのための薬物療法 pharmacologic management of the third stage of labor
4. 妊娠付属物遺残 retained products of conception
5. 妊娠中絶の概要 overview of pregnancy termination

English Journal

Risk factors for obstetric morbidity in patients with uterine atony undergoing Caesarean delivery†

Butwick AJ1, Carvalho B2, El-Sayed YY3.
British journal of anaesthesia.Br J Anaesth.2014 Jun 6. pii: aeu150. [Epub ahead of print]
BACKGROUND: Uterine atony (UA) is recognized as a leading cause of postpartum haemorrhage. However, knowledge of risk factors of haemorrhage-related morbidity among patients diagnosed with UA is uncertain. We investigated risk factors for haemorrhage-related morbidity among patients undergoing Caesa
PMID 24907281

Multidisciplinary simulation drills improve efficiency of emergency medication retrieval.

Daniels K1, Clark A, Lipman S, Puck A, Arafeh J, Chetty S.
Obstetrics and gynecology.Obstet Gynecol.2014 May;123 Suppl 1:143S-4S. doi: 10.1097/01.AOG.0000447124.24190.ec.
INTRODUCTION: Postpartum hemorrhage resulting from uterine atony is one of the leading causes of maternal morbidity. If initial treatment for atony is unsuccessful, second-line uterotonics must be administered immediately.METHODS: A retrospective observational study was performed to evaluate barrier
PMID 24770020

Methylergometrine: adverse effects in breastfed infants.

[No authors listed]
Prescrire international.Prescrire Int.2014 Apr;23(148):102.
PMID 24860899

Japanese Journal

マレイン酸メチルエルゴメトリンによって誘発された産褥痙攣発作の一例

西山幸江,山室理,加藤紀子,倉内修,茶谷順也,大野泰正
日本周産期・新生児医学会雑誌 = Journal of Japan Society of Perinatal and Neonatal Medicine 42(1), 101-104, 2006-04-20
NAID 10017415380

マレイン酸メチルエルゴメトリンをコントロールとした〓帰調血飲の産褥管理における有用性のメタアナリシス

濃沼政美,成川仁之,亀井美和子,白神誠
日本東洋醫學雜誌 57(1), 45-55, 2006-01-20
【目的】EBMが治療法選択の標準となった現在, 漢方薬においてもその基本を無視することは出来ない。そこで本研究は漢方薬のエビデンスを確立する一つの手法としてランダム化臨床試験(RCT)が実施されている漢方薬に対してMeta-Analysis(MA)を実践し, 得られたデータについて検討を行った。そこで今回はマレイン酸メチルエルゴメトリン(MME)を対照とした〓帰調血飲(KCI)の産褥管理における有 …
NAID 10020809873

「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
Mol. 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
Melt. point	172 °C (342 °F)
Solubility in water	insoluble mg/mL (20 °C)
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