Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25N3O2 |
Molecular Weight | 339.4314 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO
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
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00353Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/006035Orig1S078.pdf
Sources: http://www.drugbank.ca/drugs/DB00353
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2056 Sources: http://www.drugbank.ca/drugs/DB00353 |
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Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20958049 |
21.38 nM [EC50] | ||
Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11104741 |
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Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11104741 |
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Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11104741 |
0.49 nM [Ki] | ||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11104741 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | METHERGINE Approved UseFollowing 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 Date1946 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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 Sources: Hypothermia Hypertonicity Jerky movement NOS Convulsions |
0.8 mg multiple, oral Highest studied dose Dose: 0.8 mg Route: oral Route: multiple Dose: 0.8 mg Sources: |
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 Sources: Cerebrovascular accident |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
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Coronary artery spasm triggered by oral administration of methylergometrine. | 1991 Aug 3 |
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Delayed vasospasm in late postpartum cerebral angiopathy after withdrawal of methylergometrine. | 2002 |
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Pregnancy with acute intermittent porphyria: a case report and review of literature. | 2002 Jun |
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Postpartum hemorrhage: new management options. | 2002 Jun |
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The human G protein beta 3 subunit GNB3 825T polymorphism. | 2002 May |
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Mouse model of Prinzmetal angina by disruption of the inward rectifier Kir6.1. | 2002 May |
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Prevention and treatment of postpartum endometritis. | 2003 Aug |
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Pharmacological characterization of 5-HT(1B) receptor-mediated inhibition of local excitatory synaptic transmission in the CA1 region of rat hippocampus. | 2003 Jan |
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Effects of methylergometrine and oxytocin on thoracic epidural pressure during cesarean section. | 2003 Jun |
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Postpartum second degree heart block induced by Methergine. | 2003 May |
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B-Lynch Brace Suturing in primary post-partum hemorrhage during cesarean section. | 2003 Oct |
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Myocardial ischemia induced by intramyometrial injection of methylergonovine maleate. | 2004 Apr |
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Skeletonization does not influence internal thoracic artery innervation. | 2004 Apr |
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Misoprostol versus methylergometrine: pharmacokinetics in human milk. | 2004 Dec |
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[Revelation of a coronary spasm using the Méthergin test]. | 2004 Jan 24 |
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Acute postpuerperal necrotizing endomyometritis. | 2004 Jul |
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[Tako-tsubo: a rare form of transient left ventricular dysfunction]. | 2005 Apr |
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Accidental child poisoning with methylergometrine intended for the mother. | 2005 Feb |
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[Acute myocardial infarction due to coronary artery spasm after caesarean section]. | 2005 Jan |
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Methylergonovine maleate (methergine) relieves postdural puncture headache in obstetric patients. | 2005 Jan |
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Oral misoprostol versus injectable methylergometrine in management of the third stage of labor. | 2005 Nov |
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Myocardial infarction and mortality caused by methylergonovine. | 2005 Oct |
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The MFMU Cesarean Registry: uterine atony after primary cesarean delivery. | 2005 Sep |
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The role of serendipity in drug discovery. | 2006 |
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[Intraoperative anaphylactic shock induced by methylergometrine and oxytocin]. | 2006 Apr |
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[B lynch suture for post partum heamorrhage due to uterine atony]. | 2006 Feb |
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Effect of estradiol 17beta upon coronary artery vasoconstrictor response to methylergometrine maleate in female menopausal patients. | 2006 Feb 15 |
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[Myocardial bridging and coronary spasm on effort]. | 2006 Jan |
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[Effects of methylergometrine and oxytocin on blood loss and uterine contraction during cesarean section]. | 2006 May |
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Oral misoprostol for the prevention of primary post-partum hemorrhage during third stage of labor. | 2007 Dec |
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[Two cases of congenital airway obstruction managed with ex utero intrapartum treatment procedures: anesthetic implications]. | 2007 Jan |
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Early lactation performance in primiparous and multiparous women in relation to different maternity home practices. A randomised trial in St. Petersburg. | 2007 May 8 |
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[Case report of a successful pregnancy following thrombolysis for acute myocardial infarction]. | 2007 Nov |
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A study of prophylactic use of 15-methyl prostalglandin F2alpha in the active management of third stage of labour. | 2007 Sep |
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Complete uterine inversion during caesarean section: A case report. | 2008 Aug 27 |
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[Case of peripartum cardiomyopathy developed after an emergency cesarean section--a case report]. | 2008 Feb |
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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 |
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Low-dose sublingual misoprostol versus methylergometrine for active management of the third stage of labor. | 2008 Oct |
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Postpartum severe sinus bradycardia following methylergonovine administration. | 2008 Sep-Oct |
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Appetite suppressants, cardiac valve disease and combination pharmacotherapy. | 2009 Jul-Aug |
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Coronary artery spasm and dobutamine stress echocardiography. | 2009 Jun |
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Acute myocardial infarction following oral methyl-ergometrine intake. | 2009 Mar |
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Management of cardiac arrest caused by coronary artery spasm: epinephrine/adrenaline versus nitrates. | 2009 May-Jun |
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Efavirenz: a decade of clinical experience in the treatment of HIV. | 2009 Nov |
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Emergent management of postpartum hemorrhage for the general and acute care surgeon. | 2009 Nov 25 |
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Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study. | 2009 Nov 8 |
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Association of ornithine transcarbamylase gene polymorphisms with hypertension and coronary artery vasomotion. | 2009 Sep |
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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 |
|
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
Sources: https://www.drugs.com/dosage/methergine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2905083
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
admin
on
Sat Dec 16 17:45:11 GMT 2023
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Record UNII |
W53L6FE61V
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C47795
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NDF-RT |
N0000007618
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N0000175827
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QG02AB01
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WHO-ATC |
G02AC01
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QG02AC01
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G02AB01
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N0000007618
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m7412
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1764
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DB00353
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113-42-8
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3364
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Methylergonovine
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CHEMBL1201356
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204-027-0
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METHYLERGOMETRINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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PARENT -> METABOLITE ACTIVE |
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
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