U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N3O2
Molecular Weight 339.4322
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLERGONOVINE

SMILES

CC[C@@]([H])(CO)N=C([C@]1([H])C=C2c3cccc4c3c(C[C@@]2([H])N(C)C1)c[nH]4)O

InChI

InChIKey=UNBRKDKAWYKMIV-QWQRMKEZSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: 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

-729648000000
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
Effect of direct intracoronary administration of methylergonovine in patients with and without variant angina.
1991 Apr
Coronary artery spasm triggered by oral administration of methylergometrine.
1991 Aug 3
A comparison of propofol and ketamine as induction agents for cesarean section.
2004 Jul
[Time course of thoracic epidural pressure and saphenous venous pressure changes with oxytocics after fetus delivery in parturients undergoing cesarean section].
2004 Oct
[Tako-tsubo: a rare form of transient left ventricular dysfunction].
2005 Apr
Accidental child poisoning with methylergometrine intended for the mother.
2005 Feb
Neonatal ergot poisoning: a persistent iatrogenic illness.
2005 Jul
Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist.
2005 May-Jun
Oral misoprostol versus injectable methylergometrine in management of the third stage of labor.
2005 Nov
Myocardial infarction and mortality caused by methylergonovine.
2005 Oct
The MFMU Cesarean Registry: uterine atony after primary cesarean delivery.
2005 Sep
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
[Intraoperative anaphylactic shock induced by methylergometrine and oxytocin].
2006 Apr
Stability of oral liquid preparations of methylergometrine.
2006 Aug
[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
[Myocardial bridging and coronary spasm on effort].
2006 Jan
Clinical characteristics of patients with exercise-induced ST-segment elevation without prior myocardial infarction.
2006 Mar
[Effects of methylergometrine and oxytocin on blood loss and uterine contraction during cesarean section].
2006 May
Oral misoprostol for the prevention of primary post-partum hemorrhage during third stage of labor.
2007 Dec
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.
2007 Jun
[Case report of a successful pregnancy following thrombolysis for acute myocardial infarction].
2007 Nov
Intraumbilical injection of uterotonics for retained placenta.
2007 Nov
A study of prophylactic use of 15-methyl prostalglandin F2alpha in the active management of third stage of labour.
2007 Sep
Diagnosis and treatment of peripartum bleeding.
2008
Complete uterine inversion during caesarean section: A case report.
2008 Aug 27
[Case of peripartum cardiomyopathy developed after an emergency cesarean section--a case report].
2008 Feb
Efficacy of rectal misoprostol as second-line therapy for the treatment of primary postpartum hemorrhage.
2008 Mar
Signs of myocardial ischaemia after injection of oxytocin: a randomized double-blind comparison of oxytocin and methylergometrine during Caesarean section.
2008 May
History of methysergide in migraine.
2008 Nov
Bromocriptine, a dopamine D(2) receptor agonist with the structure of the amino acid ergot alkaloids, induces neurite outgrowth in PC12 cells.
2008 Nov 19
Low-dose sublingual misoprostol versus methylergometrine for active management of the third stage of labor.
2008 Oct
Methylergometrine poisoning in the newborn: report of two cases.
2008 Sep
Postpartum severe sinus bradycardia following methylergonovine administration.
2008 Sep-Oct
Early postpartum hemorrhage after induction of labor.
2008 Sep-Oct
Anaesthesiological considerations on tocolytic and uterotonic therapy in obstetrics.
2009 Jul
Appetite suppressants, cardiac valve disease and combination pharmacotherapy.
2009 Jul-Aug
Sudden cardiac arrest during cesarean section -- a possible case of amniotic fluid embolism.
2009 Jun
Management of cardiac arrest caused by coronary artery spasm: epinephrine/adrenaline versus nitrates.
2009 May-Jun
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
Emergent management of postpartum hemorrhage for the general and acute care surgeon.
2009 Nov 25
Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study.
2009 Nov 8
Association of ornithine transcarbamylase gene polymorphisms with hypertension and coronary artery vasomotion.
2009 Sep
Severe vaginal bleeding secondary to cesarean scar dehiscence following incomplete abortion management.
2010 Feb
Human immunodeficiency virus and pregnancy.
2010 May
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
Route of Administration: Other
Name Type Language
METHYLERGONOVINE
MI   VANDF  
Common Name English
METHYLERGOMETRINE [HSDB]
Common Name English
(8.BETA.)-N-((1S)-1-(HYDROXYMETHYL)PROPYL)-6-METHYL-9,10-DIDEHYDROERGOLINE-8-CARBOXAMIDE
Systematic Name English
ERGOTYL
Brand Name English
METHYLERGOMETRINE [WHO-DD]
Common Name English
METHYLERGOMETRINE [INN]
Common Name English
METHYLERGONOVINE [VANDF]
Common Name English
METHYLERGONOVINE [MI]
Common Name English
METHYLERGOMETRINE
HSDB   INN   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
NDF-RT N0000007618
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
NDF-RT N0000175827
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
WHO-VATC QG02AB01
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
WHO-ATC G02AC01
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
WHO-VATC QG02AC01
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
WHO-ATC G02AB01
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
NDF-RT N0000007618
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
Code System Code Type Description
EPA CompTox
113-42-8
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
MERCK INDEX
M7412
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C74105
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
EVMPD
SUB08868MIG
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
INN
2900
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
RXCUI
6883
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY RxNorm
PUBCHEM
8226
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
DRUG CENTRAL
1764
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
DRUG BANK
DB00353
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
CAS
113-42-8
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
HSDB
3364
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
LACTMED
Methylergonovine
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201356
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
IUPHAR
150
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
FDA UNII
W53L6FE61V
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
MESH
D008755
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-027-0
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY
WIKIPEDIA
METHYLERGOMETRINE
Created by admin on Sat Jun 26 02:20:11 UTC 2021 , Edited by admin on Sat Jun 26 02:20:11 UTC 2021
PRIMARY