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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.CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1.CC[C@@H](CO)NC(=O)[C@H]5CN(C)[C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5

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

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

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

1946
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
0.2 mg single, intravenous
Recommended
Dose: 0.2 mg
Route: intravenous
Route: single
Dose: 0.2 mg
Sources:
unhealthy
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
Hypertension
0.2 mg single, intravenous
Recommended
Dose: 0.2 mg
Route: intravenous
Route: single
Dose: 0.2 mg
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Application of uterotonics on the basis of regular ultrasonic evaluation of the uterus prevents unnecessary surgical intervention in the postpartum period.
2010-09
Human immunodeficiency virus and pregnancy.
2010-05
Severe vaginal bleeding secondary to cesarean scar dehiscence following incomplete abortion management.
2010-02
Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital.
2010-01-26
Emergent management of postpartum hemorrhage for the general and acute care surgeon.
2009-11-25
Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study.
2009-11-08
Efavirenz: a decade of clinical experience in the treatment of HIV.
2009-11
Comparison of sublingual misoprostol, intravenous oxytocin, and intravenous methylergometrine in active management of the third stage of labor.
2009-11
Association of ornithine transcarbamylase gene polymorphisms with hypertension and coronary artery vasomotion.
2009-09
Anaesthesiological considerations on tocolytic and uterotonic therapy in obstetrics.
2009-07
Sudden cardiac arrest during cesarean section -- a possible case of amniotic fluid embolism.
2009-06
Coronary artery spasm and dobutamine stress echocardiography.
2009-06
Uterine preservation in a woman with spontaneous uterine rupture secondary to placenta percreta on the posterior wall: a case report.
2009-04
Acute myocardial infarction following oral methyl-ergometrine intake.
2009-03
Appetite suppressants, cardiac valve disease and combination pharmacotherapy.
2008-12-19
Prophylaxis of migraine: general principles and patient acceptance.
2008-12
[A case of pulmonary alveolar hemorrhage caused by methylergometrine].
2008-12
Bromocriptine, a dopamine D(2) receptor agonist with the structure of the amino acid ergot alkaloids, induces neurite outgrowth in PC12 cells.
2008-11-19
History of methysergide in migraine.
2008-11
Postpartum severe sinus bradycardia following methylergonovine administration.
2008-10-04
Low-dose sublingual misoprostol versus methylergometrine for active management of the third stage of labor.
2008-10
Early postpartum hemorrhage after induction of labor.
2008-09-02
Methylergometrine poisoning in the newborn: report of two cases.
2008-09
Complete uterine inversion during caesarean section: A case report.
2008-08-27
Signs of myocardial ischaemia after injection of oxytocin: a randomized double-blind comparison of oxytocin and methylergometrine during Caesarean section.
2008-05
Efficacy of rectal misoprostol as second-line therapy for the treatment of primary postpartum hemorrhage.
2008-03
[Case of peripartum cardiomyopathy developed after an emergency cesarean section--a case report].
2008-02
Diagnosis and treatment of peripartum bleeding.
2008
Eclipsed mitral regurgitation: a new form of functional mitral regurgitation for an unusual cause of heart failure with normal ejection fraction.
2008
Oral misoprostol for the prevention of primary post-partum hemorrhage during third stage of labor.
2007-12
Management of cardiac arrest caused by coronary artery spasm: epinephrine/adrenaline versus nitrates.
2007-11-25
[Case report of a successful pregnancy following thrombolysis for acute myocardial infarction].
2007-11
Intraumbilical injection of uterotonics for retained placenta.
2007-11
A study of prophylactic use of 15-methyl prostalglandin F2alpha in the active management of third stage of labour.
2007-09
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.
2007-06
Early lactation performance in primiparous and multiparous women in relation to different maternity home practices. A randomised trial in St. Petersburg.
2007-05-08
[Two cases of congenital airway obstruction managed with ex utero intrapartum treatment procedures: anesthetic implications].
2007-01
Improved migraine management in primary care: results of a patient treatment experience study using zolmitriptan orally disintegrating tablet.
2006-12
Stability of oral liquid preparations of methylergometrine.
2006-08
[Heart and freezer: about one case of hypereosinophilia and coronary spasm].
2006-08
[Effects of methylergometrine and oxytocin on blood loss and uterine contraction during cesarean section].
2006-05
[Intraoperative anaphylactic shock induced by methylergometrine and oxytocin].
2006-04
Clinical characteristics of patients with exercise-induced ST-segment elevation without prior myocardial infarction.
2006-03
[B lynch suture for post partum heamorrhage due to uterine atony].
2006-02
The role of serendipity in drug discovery.
2006
Prevention of postpartum hemorrhage by uterotonic agents: comparison of oxytocin and methylergometrine in the management of the third stage of labor.
2006
Effect of enhancement of uterine involution and earlier initiation of post-partum cyclicity on the reproductive performance of buffalo.
2006
Is methergine alone sufficient in relieving postdural puncture headache?
2006
Coronary artery spasm triggered by oral administration of methylergometrine.
1991-08-03
Effect of direct intracoronary administration of methylergonovine in patients with and without variant angina.
1991-04
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 Mon Mar 31 17:57:44 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:44 GMT 2025
Record UNII
5EDH242U9O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLERGONOVINE TARTRATE
Common Name English
ERGOLINE-8.BETA.-CARBOXAMIDE, 9,10-DIDEHYDRO-N-((S)-1-(HYDROXYMETHYL)PROPYL)-6-METHYL-, TARTRATE (2:1) (SALT)
Preferred Name English
Methylergometrine tartrate
Common Name English
METHERGINE TARTRATE
Common Name English
Methylergometrine tartrate [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
71586892
Created by admin on Mon Mar 31 17:57:44 GMT 2025 , Edited by admin on Mon Mar 31 17:57:44 GMT 2025
PRIMARY
FDA UNII
5EDH242U9O
Created by admin on Mon Mar 31 17:57:44 GMT 2025 , Edited by admin on Mon Mar 31 17:57:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID60211130
Created by admin on Mon Mar 31 17:57:44 GMT 2025 , Edited by admin on Mon Mar 31 17:57:44 GMT 2025
PRIMARY
DRUG BANK
DBSALT001062
Created by admin on Mon Mar 31 17:57:44 GMT 2025 , Edited by admin on Mon Mar 31 17:57:44 GMT 2025
PRIMARY
CAS
6209-37-6
Created by admin on Mon Mar 31 17:57:44 GMT 2025 , Edited by admin on Mon Mar 31 17:57:44 GMT 2025
PRIMARY
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