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
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 |
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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: |
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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: |
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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: |
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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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Effect of direct intracoronary administration of methylergonovine in patients with and without variant angina. | 1991 Apr |
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Coronary artery spasm triggered by oral administration of methylergometrine. | 1991 Aug 3 |
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Misoprostol versus methylergometrine: pharmacokinetics in human milk. | 2004 Dec |
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A comparison of propofol and ketamine as induction agents for cesarean section. | 2004 Jul |
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Sublingual misoprostol versus methylergometrine for active management of the third stage of labor. | 2004 Oct |
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[Tako-tsubo: a rare form of transient left ventricular dysfunction]. | 2005 Apr |
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Methylergonovine maleate (methergine) relieves postdural puncture headache in obstetric patients. | 2005 Jan |
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Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. | 2005 May-Jun |
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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 role of serendipity in drug discovery. | 2006 |
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Prevention of postpartum hemorrhage by uterotonic agents: comparison of oxytocin and methylergometrine in the management of the third stage of labor. | 2006 |
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Effect of enhancement of uterine involution and earlier initiation of post-partum cyclicity on the reproductive performance of buffalo. | 2006 |
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Is methergine alone sufficient in relieving postdural puncture headache? | 2006 |
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[Intraoperative anaphylactic shock induced by methylergometrine and oxytocin]. | 2006 Apr |
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Stability of oral liquid preparations of methylergometrine. | 2006 Aug |
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[Heart and freezer: about one case of hypereosinophilia and coronary spasm]. | 2006 Aug |
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Improved migraine management in primary care: results of a patient treatment experience study using zolmitriptan orally disintegrating tablet. | 2006 Dec |
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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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[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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Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage. | 2007 Jun |
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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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Intraumbilical injection of uterotonics for retained placenta. | 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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Diagnosis and treatment of peripartum bleeding. | 2008 |
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Eclipsed mitral regurgitation: a new form of functional mitral regurgitation for an unusual cause of heart failure with normal ejection fraction. | 2008 |
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Complete uterine inversion during caesarean section: A case report. | 2008 Aug 27 |
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Prophylaxis of migraine: general principles and patient acceptance. | 2008 Dec |
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[Case of peripartum cardiomyopathy developed after an emergency cesarean section--a case report]. | 2008 Feb |
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Efficacy of rectal misoprostol as second-line therapy for the treatment of primary postpartum hemorrhage. | 2008 Mar |
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Signs of myocardial ischaemia after injection of oxytocin: a randomized double-blind comparison of oxytocin and methylergometrine during Caesarean section. | 2008 May |
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History of methysergide in migraine. | 2008 Nov |
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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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Early postpartum hemorrhage after induction of labor. | 2008 Sep-Oct |
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Anaesthesiological considerations on tocolytic and uterotonic therapy in obstetrics. | 2009 Jul |
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Appetite suppressants, cardiac valve disease and combination pharmacotherapy. | 2009 Jul-Aug |
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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 |
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Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital. | 2010 Jan 26 |
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Human immunodeficiency virus and pregnancy. | 2010 May |
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
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Classification Tree | Code System | Code | ||
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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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NDF-RT |
N0000007618
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DTXSID00904978
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m7412
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C74105
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100000080906
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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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150
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D008755
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204-027-0
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METHYLERGOMETRINE
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)