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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C20H25N3O2.C4H6O6
Molecular Weight 828.9496
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLERGONOVINE TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO.[H][C@@]56CC7=CNC8=C7C(=CC=C8)C5=C[C@H](CN6C)C(=O)N[C@@H](CC)CO

InChI

InChIKey=UAQLRIJPUUAYIG-CRKBDDFUSA-N
InChI=1S/2C20H25N3O2.C4H6O6/c2*1-3-14(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;5-1(3(7)8)2(6)4(9)10/h2*4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25);1-2,5-6H,(H,7,8)(H,9,10)/t2*13-,14+,18-;1-,2-/m111/s1

HIDE SMILES / InChI

Molecular Formula C20H25N3O2
Molecular Weight 339.4314
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/006035Orig1S078.pdf

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. In general, the effects of all the ergot alkaloids appear to results from their actions as partial agonists or antagonists at adrenergic, dopaminergic, and tryptaminergic receptors. The spectrum of effects depends on the agent, dosage, species, tissue, and experimental or physiological conditions. All of the alkaloids of ergot significantly increase the motor activity of the uterus. After small doses contractions are increased in force or frequency, or both, but are followed by a normal degree of relaxation. As the dose is increased, contractions become more forceful and prolonged, resting tonus is markedly increased, and sustained contracture can result. Methylergometrine acts directly on the smooth muscle of the uterus and increases the tone, rate, and amplitude of rhythmic contractions through binding and the resultant antagonism of the dopamine D1 receptor. Thus, it induces a rapid and sustained tetanic uterotonic effect which shortens the third stage of labor and reduces blood loss. Methylergometrine is used for the prevention and control of excessive bleeding following vaginal childbirth.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
METHERGINE

Approved Use

Following delivery of the placenta, for routine management of uterine atony, hemorrhage and subinvolution of the uterus. For control of uterine hemorrhage in the second stage of labor following delivery of the anterior shoulder.

Launch Date

-7.2964801E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5918 pg/mL
0.2 mg single, intramuscular
dose: 0.2 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
METHYLERGONOVINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
13889 pg × h/mL
0.2 mg single, intramuscular
dose: 0.2 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
METHYLERGONOVINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.39 h
0.2 mg single, intramuscular
dose: 0.2 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
METHYLERGONOVINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
0.2 mg single, intramuscular
Overdose
Dose: 0.2 mg
Route: intramuscular
Route: single
Dose: 0.2 mg
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sources:
Other AEs: Respiratory depression, Hypothermia...
Other AEs:
Respiratory depression
Hypothermia
Hypertonicity
Jerky movement NOS
Convulsions
Sources:
0.8 mg multiple, oral
Highest studied dose
healthy
Health Status: healthy
Condition: uterine atony and hemorrhage prophylaxis
Sex: F
Sources:
0.2 mg single, intravenous
Recommended
Dose: 0.2 mg
Route: intravenous
Route: single
Dose: 0.2 mg
Sources:
unhealthy
Health Status: unhealthy
Condition: uterine hemorrhage
Sources:
Other AEs: Hypertension, Cerebrovascular accident...
Other AEs:
Hypertension
Cerebrovascular accident
Sources:
AEs

AEs

AESignificanceDosePopulation
Convulsions
0.2 mg single, intramuscular
Overdose
Dose: 0.2 mg
Route: intramuscular
Route: single
Dose: 0.2 mg
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sources:
Hypertonicity
0.2 mg single, intramuscular
Overdose
Dose: 0.2 mg
Route: intramuscular
Route: single
Dose: 0.2 mg
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sources:
Hypothermia
0.2 mg single, intramuscular
Overdose
Dose: 0.2 mg
Route: intramuscular
Route: single
Dose: 0.2 mg
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sources:
Jerky movement NOS
0.2 mg single, intramuscular
Overdose
Dose: 0.2 mg
Route: intramuscular
Route: single
Dose: 0.2 mg
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sources:
Respiratory depression
0.2 mg single, intramuscular
Overdose
Dose: 0.2 mg
Route: intramuscular
Route: single
Dose: 0.2 mg
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sources:
Cerebrovascular accident
0.2 mg single, intravenous
Recommended
Dose: 0.2 mg
Route: intravenous
Route: single
Dose: 0.2 mg
Sources:
unhealthy
Health Status: unhealthy
Condition: uterine hemorrhage
Sources:
Hypertension
0.2 mg single, intravenous
Recommended
Dose: 0.2 mg
Route: intravenous
Route: single
Dose: 0.2 mg
Sources:
unhealthy
Health Status: unhealthy
Condition: uterine hemorrhage
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Postpartum hypertension and convulsion after oxytocic drugs.
1976 Nov-Dec
Coronary artery spasm triggered by oral administration of methylergometrine.
1991 Aug 3
Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications.
2000 Dec 5
Successful pregnancy after the noninvasive management of uterine arteriovenous malformation.
2001 Dec
The human G-protein beta3 subunit C825T polymorphism is associated with coronary artery vasoconstriction.
2001 May
Delayed vasospasm in late postpartum cerebral angiopathy after withdrawal of methylergometrine.
2002
Pregnancy with acute intermittent porphyria: a case report and review of literature.
2002 Jun
Prevention and treatment of postpartum endometritis.
2003 Aug
[Mitral insufficiency related to a spasm of the left anterior descending artery. A case report].
2003 Jan
[Dysfunctional uterine bleeding: medical therapies].
2003 Jun
[Postpartum cerebral angiopathy--a case report the vasculopathy associated with co-administration of two vasoconstrictives, methylergometrine maleate and sumatriptan].
2004 Feb
Acute postpuerperal necrotizing endomyometritis.
2004 Jul
Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation.
2004 May 15
[Tako-tsubo: a rare form of transient left ventricular dysfunction].
2005 Apr
Myocardial infarction and mortality caused by methylergonovine.
2005 Oct
Prevention of postpartum hemorrhage by uterotonic agents: comparison of oxytocin and methylergometrine in the management of the third stage of labor.
2006
[Heart and freezer: about one case of hypereosinophilia and coronary spasm].
2006 Aug
[B lynch suture for post partum heamorrhage due to uterine atony].
2006 Feb
Effect of estradiol 17beta upon coronary artery vasoconstrictor response to methylergometrine maleate in female menopausal patients.
2006 Feb 15
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.
2007 Jun
[Case of peripartum cardiomyopathy developed after an emergency cesarean section--a case report].
2008 Feb
Low-dose sublingual misoprostol versus methylergometrine for active management of the third stage of labor.
2008 Oct
Postpartum severe sinus bradycardia following methylergonovine administration.
2008 Sep-Oct
Uterine preservation in a woman with spontaneous uterine rupture secondary to placenta percreta on the posterior wall: a case report.
2009 Apr
Appetite suppressants, cardiac valve disease and combination pharmacotherapy.
2009 Jul-Aug
Efavirenz: a decade of clinical experience in the treatment of HIV.
2009 Nov
Comparison of sublingual misoprostol, intravenous oxytocin, and intravenous methylergometrine in active management of the third stage of labor.
2009 Nov
Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study.
2009 Nov 8
Application of uterotonics on the basis of regular ultrasonic evaluation of the uterus prevents unnecessary surgical intervention in the postpartum period.
2010 Sep
Patents

Sample Use Guides

Intramuscularly 1 mL, 0.2 mg, after delivery of the anterior shoulder, after delivery of the placenta, or during the puerperium. May be repeated as required, at intervals of 2-4 hours. Intravenously 1 mL, 0.2 mg, administered slowly over a period of no less than 60 seconds Orally One tablet, 0.2 mg, 3 or 4 times daily in the puerperium for a maximum of 1 week.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:26:20 UTC 2023
Edited
by admin
on Fri Dec 15 15:26:20 UTC 2023
Record UNII
5EDH242U9O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLERGONOVINE TARTRATE
Common Name English
Methylergometrine tartrate
Common Name English
METHERGINE TARTRATE
Common Name English
ERGOLINE-8.BETA.-CARBOXAMIDE, 9,10-DIDEHYDRO-N-((S)-1-(HYDROXYMETHYL)PROPYL)-6-METHYL-, TARTRATE (2:1) (SALT)
Common Name English
Methylergometrine tartrate [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
71586892
Created by admin on Fri Dec 15 15:26:20 UTC 2023 , Edited by admin on Fri Dec 15 15:26:20 UTC 2023
PRIMARY
FDA UNII
5EDH242U9O
Created by admin on Fri Dec 15 15:26:20 UTC 2023 , Edited by admin on Fri Dec 15 15:26:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID60211130
Created by admin on Fri Dec 15 15:26:20 UTC 2023 , Edited by admin on Fri Dec 15 15:26:20 UTC 2023
PRIMARY
DRUG BANK
DBSALT001062
Created by admin on Fri Dec 15 15:26:20 UTC 2023 , Edited by admin on Fri Dec 15 15:26:20 UTC 2023
PRIMARY
CAS
6209-37-6
Created by admin on Fri Dec 15 15:26:20 UTC 2023 , Edited by admin on Fri Dec 15 15:26:20 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY