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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N3O2.C4H4O4
Molecular Weight 455.5036
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of METHYLERGONOVINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1

InChI

InChIKey=NOFOWWRHEPHDCY-DAUURJMHSA-N
InChI=1S/C20H25N3O2.C4H4O4/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;5-3(6)1-2-4(7)8/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t13-,14+,18-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C20H25N3O2
Molecular Weight 339.4314
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

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
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
[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
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
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
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
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
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
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
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

In Vivo Use Guide
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: Intramuscularly, Intravenously, Orally
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:08:54 UTC 2019
Edited
by admin
on Tue Oct 22 06:08:54 UTC 2019
Record UNII
IR84JPZ1RK
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYLERGONOVINE MALEATE
MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N-(1-(HYDROXYMETHYL)PROPYL)-6-METHYL-, (8.BETA.(S))-, (Z)-2-BUTENEDIOATE
Common Name English
9,10-DIDEHYDRO-N-((S)-1-(HYDROXYMETHYL)PROPYL)-6-METHYLERGOLINE-8.BETA.-CARBOXAMIDE MALEATE
Common Name English
METHYLERGONOVINE MALEATE [USP]
Common Name English
METHYLERGOMETRINE MALEATE [WHO-DD]
Common Name English
METHYLERGONOVINE MALEATE [VANDF]
Common Name English
METHYLERGONOVINE MALEATE [USP-RS]
Common Name English
METHYLERGOMETRINE MALEATE
JAN   MART.   WHO-DD  
Common Name English
METHYLERGOMETRINE MALEATE [JAN]
Common Name English
METHYLERGOMETRINE MALEATE [MART.]
Common Name English
METHYLERGONOVINE MALEATE [ORANGE BOOK]
Common Name English
METHERGINE
Brand Name English
METHYLERGONOVINE MALEATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
Code System Code Type Description
MERCK INDEX
M7412
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY Merck Index
PUBCHEM
5281072
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY
RXCUI
84158
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C47618
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY
EVMPD
SUB03247MIG
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY
CAS
7054-07-1
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
SUPERCEDED
ChEMBL
CHEMBL1201356
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY
CAS
57432-61-8
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY
ECHA (EC/EINECS)
260-734-4
Created by admin on Tue Oct 22 06:08:54 UTC 2019 , Edited by admin on Tue Oct 22 06:08:54 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY