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
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
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 |
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 |
|||
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 |
|||
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11104741 |
|||
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 Date-7.2964801E11 |
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 |
---|---|---|
Postpartum hypertension and convulsion after oxytocic drugs. | 1976 Nov-Dec |
|
Coronary artery spasm triggered by oral administration of methylergometrine. | 1991 Aug 3 |
|
Acute myocardial infarction associated with postpartum ergot alkaloid administration. | 1999 Jan |
|
The human G-protein beta3 subunit C825T polymorphism is associated with coronary artery vasoconstriction. | 2001 May |
|
Delayed vasospasm in late postpartum cerebral angiopathy after withdrawal of methylergometrine. | 2002 |
|
Postpartum hemorrhage: new management options. | 2002 Jun |
|
The human G protein beta 3 subunit GNB3 825T polymorphism. | 2002 May |
|
Mouse model of Prinzmetal angina by disruption of the inward rectifier Kir6.1. | 2002 May |
|
[Drug packaging and context of use as a cause of intoxication]. | 2002 May-Jun |
|
Methylergometrine poisoning in children: review of 34 cases. | 2003 |
|
Myocardial ischemia induced by intramyometrial injection of methylergonovine maleate. | 2004 Apr |
|
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. | 2004 Aug |
|
[Revelation of a coronary spasm using the Méthergin test]. | 2004 Jan 24 |
|
Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation. | 2004 May 15 |
|
Terbutaline and methergine in look-alike packaging. | 2004 May-Jun |
|
An unusual presentation of idiopathic thrombocytopenic purpura in pregnancy. | 2005 Feb |
|
Oral misoprostol versus injectable methylergometrine in management of the third stage of labor. | 2005 Nov |
|
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 |
|
Stability of oral liquid preparations of methylergometrine. | 2006 Aug |
|
[Heart and freezer: about one case of hypereosinophilia and coronary spasm]. | 2006 Aug |
|
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 |
|
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 |
|
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 |
|
Prophylaxis of migraine: general principles and patient acceptance. | 2008 Dec |
|
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 |
|
Comparison of sublingual misoprostol, intravenous oxytocin, and intravenous methylergometrine in active management of the third stage of labor. | 2009 Nov |
|
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 |
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
Wed Jul 05 22:56:24 UTC 2023
by
admin
on
Wed Jul 05 22:56:24 UTC 2023
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Record UNII |
5EDH242U9O
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Record Status |
Validated (UNII)
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Record Version |
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5EDH242U9O
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DTXSID60211130
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DBSALT001062
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6209-37-6
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ACTIVE MOIETY |
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