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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

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
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
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
[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
[Intraoperative anaphylactic shock induced by methylergometrine and oxytocin].
2006 Apr
Improved migraine management in primary care: results of a patient treatment experience study using zolmitriptan orally disintegrating tablet.
2006 Dec
[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
[Two cases of congenital airway obstruction managed with ex utero intrapartum treatment procedures: anesthetic implications].
2007 Jan
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.
2007 Jun
Early lactation performance in primiparous and multiparous women in relation to different maternity home practices. A randomised trial in St. Petersburg.
2007 May 8
[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
Eclipsed mitral regurgitation: a new form of functional mitral regurgitation for an unusual cause of heart failure with normal ejection fraction.
2008
Complete uterine inversion during caesarean section: A case report.
2008 Aug 27
Prophylaxis of migraine: general principles and patient acceptance.
2008 Dec
[A case of pulmonary alveolar hemorrhage caused by methylergometrine].
2008 Dec
[Case of peripartum cardiomyopathy developed after an emergency cesarean section--a case report].
2008 Feb
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
Uterine preservation in a woman with spontaneous uterine rupture secondary to placenta percreta on the posterior wall: a case report.
2009 Apr
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
Coronary artery spasm and dobutamine stress echocardiography.
2009 Jun
Acute myocardial infarction following oral methyl-ergometrine intake.
2009 Mar
Management of cardiac arrest caused by coronary artery spasm: epinephrine/adrenaline versus nitrates.
2009 May-Jun
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
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
Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital.
2010 Jan 26
Human immunodeficiency virus and pregnancy.
2010 May
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:20 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:26:20 GMT 2023
PRIMARY
FDA UNII
5EDH242U9O
Created by admin on Fri Dec 15 15:26:20 GMT 2023 , Edited by admin on Fri Dec 15 15:26:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID60211130
Created by admin on Fri Dec 15 15:26:20 GMT 2023 , Edited by admin on Fri Dec 15 15:26:20 GMT 2023
PRIMARY
DRUG BANK
DBSALT001062
Created by admin on Fri Dec 15 15:26:20 GMT 2023 , Edited by admin on Fri Dec 15 15:26:20 GMT 2023
PRIMARY
CAS
6209-37-6
Created by admin on Fri Dec 15 15:26:20 GMT 2023 , Edited by admin on Fri Dec 15 15:26:20 GMT 2023
PRIMARY
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ACTIVE MOIETY