methylergonovine

メチルエルゴノビン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/08/04 10:10:35」(JST)

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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 Y
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
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 N Key:UNBRKDKAWYKMIV-QWQRMKEZSA-N N
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. 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.

Migraine

Methylergometrine is sometimes used for both prevention and acute treatment 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.

Side effects

Adverse effects include:

• Cholinergic effects such as nausea, vomiting, and diarrhea
• Dizziness
• Pulmonary hypertension
• 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.

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.

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, while blood vessels are affected to a lesser extent compared to other ergot alkaloids.

References

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. 妊娠中期の中絶：子宮内容除去術 second trimester pregnancy termination dilation and evacuation
• 3. 産後出血の概要 overview of postpartum hemorrhage
• 4. 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
• 5. 妊娠付属物遺残 retained products of conception

English Journal

• 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

• Cesarean Delivery in a Parturient with Left Ventricular Noncompaction Complicated by Acute Pulmonary Hypertension After Methylergonovine Administration for Postpartum Hemorrhage.

• Spitzer Y1, Weiner MM, Beilin Y.
• A & A case reports.A A Case Rep.2015 Jun 15;4(12):166-8. doi: 10.1213/XAA.0000000000000152.
• Left ventricular noncompaction is a rare congenital cardiomyopathy that is an arrest in the normal process of cardiac compaction, resulting in the development of multiple prominent trabeculations in the left ventricle. We report a case of a parturient with left ventricular noncompaction causing deco
• PMID 26050249

• Second-line uterotonics and the risk of hemorrhage-related morbidity.

• Butwick AJ1, Carvalho B2, Blumenfeld YJ3, El-Sayed YY3, Nelson LM4, Bateman BT5.
• American journal of obstetrics and gynecology.Am J Obstet Gynecol.2015 May;212(5):642.e1-7. doi: 10.1016/j.ajog.2015.01.008. Epub 2015 Jan 9.
• OBJECTIVE: Uterine atony is a leading cause of postpartum hemorrhage. Although most cases of postpartum hemorrhage respond to first-line therapy with uterine massage and oxytocin administration, second-line uterotonics including methylergonovine and carboprost are integral for the management of refr
• PMID 25582104

Japanese Journal

• CORONARY SPASM IN TWO SISTERS

• FUJIWARA YASUMASA,NAKAMURA TAI,YAMANAKA OSAMU,YAMAGUCHI HIROSHI
• Japanese circulation journal 57(5), 472-474, 1993-05-20
• … The 38-year-old younger sister suffered from acute inferior myocardial infarction after taking methylergonovine following an abortion. …
• NAID 110002607179

• Coronary spasm in two sisters.

• FUJIWARA YASUMASA,NAKAMURA TAI,YAMANAKA OSAMU,YAMAGUCHI HIROSHI
• JAPANESE CIRCULATION JOURNAL 57(5), 472-474, 1993
• … The 38-year-old younger sister suffered from acute inferior myocardial infarction after taking methylergonovine following an abortion. …
• NAID 130003548422

• Effect of direct intracoronary administration of methylergonovine in patients with and without variant angina

• IGARASHI Y
• Am Heart J 121, 1094-1100, 1991
• NAID 30016702882

Related Links

• Methylergometrine - Wikipedia, the free encyclopedia

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.

• Methylergonovine Oral: MedlinePlus Drug Information

Methylergonovine comes as a tablet to take by mouth three or four times a day. Follow the directions on your prescription label carefully, and ask your doctor or pharmacist to explain any part you do not understand. Take methylergonovine ...

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★リンクテーブル★

リンク元	「メチルエルゴノビン」

「メチルエルゴノビン」

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英

methylergonovine

化

マレイン酸メチルエルゴメトリン methylergometrine maleate

関

メチルエルゴメトリン methylergometrine

• 麦角アルカロイド誘導体;子宮収縮薬