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.CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1.CC[C@@H](CO)NC(=O)[C@H]5CN(C)[C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5
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 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 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 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 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 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Application of uterotonics on the basis of regular ultrasonic evaluation of the uterus prevents unnecessary surgical intervention in the postpartum period. | 2010-09 |
|
| Human immunodeficiency virus and pregnancy. | 2010-05 |
|
| Severe vaginal bleeding secondary to cesarean scar dehiscence following incomplete abortion management. | 2010-02 |
|
| Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital. | 2010-01-26 |
|
| Emergent management of postpartum hemorrhage for the general and acute care surgeon. | 2009-11-25 |
|
| Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study. | 2009-11-08 |
|
| Efavirenz: a decade of clinical experience in the treatment of HIV. | 2009-11 |
|
| Comparison of sublingual misoprostol, intravenous oxytocin, and intravenous methylergometrine in active management of the third stage of labor. | 2009-11 |
|
| Association of ornithine transcarbamylase gene polymorphisms with hypertension and coronary artery vasomotion. | 2009-09 |
|
| Anaesthesiological considerations on tocolytic and uterotonic therapy in obstetrics. | 2009-07 |
|
| Sudden cardiac arrest during cesarean section -- a possible case of amniotic fluid embolism. | 2009-06 |
|
| Coronary artery spasm and dobutamine stress echocardiography. | 2009-06 |
|
| Uterine preservation in a woman with spontaneous uterine rupture secondary to placenta percreta on the posterior wall: a case report. | 2009-04 |
|
| Acute myocardial infarction following oral methyl-ergometrine intake. | 2009-03 |
|
| Appetite suppressants, cardiac valve disease and combination pharmacotherapy. | 2008-12-19 |
|
| Prophylaxis of migraine: general principles and patient acceptance. | 2008-12 |
|
| [A case of pulmonary alveolar hemorrhage caused by methylergometrine]. | 2008-12 |
|
| Bromocriptine, a dopamine D(2) receptor agonist with the structure of the amino acid ergot alkaloids, induces neurite outgrowth in PC12 cells. | 2008-11-19 |
|
| History of methysergide in migraine. | 2008-11 |
|
| Postpartum severe sinus bradycardia following methylergonovine administration. | 2008-10-04 |
|
| Low-dose sublingual misoprostol versus methylergometrine for active management of the third stage of labor. | 2008-10 |
|
| Early postpartum hemorrhage after induction of labor. | 2008-09-02 |
|
| Methylergometrine poisoning in the newborn: report of two cases. | 2008-09 |
|
| Complete uterine inversion during caesarean section: A case report. | 2008-08-27 |
|
| Signs of myocardial ischaemia after injection of oxytocin: a randomized double-blind comparison of oxytocin and methylergometrine during Caesarean section. | 2008-05 |
|
| Efficacy of rectal misoprostol as second-line therapy for the treatment of primary postpartum hemorrhage. | 2008-03 |
|
| [Case of peripartum cardiomyopathy developed after an emergency cesarean section--a case report]. | 2008-02 |
|
| 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 |
|
| Oral misoprostol for the prevention of primary post-partum hemorrhage during third stage of labor. | 2007-12 |
|
| Management of cardiac arrest caused by coronary artery spasm: epinephrine/adrenaline versus nitrates. | 2007-11-25 |
|
| [Case report of a successful pregnancy following thrombolysis for acute myocardial infarction]. | 2007-11 |
|
| Intraumbilical injection of uterotonics for retained placenta. | 2007-11 |
|
| A study of prophylactic use of 15-methyl prostalglandin F2alpha in the active management of third stage of labour. | 2007-09 |
|
| Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage. | 2007-06 |
|
| Early lactation performance in primiparous and multiparous women in relation to different maternity home practices. A randomised trial in St. Petersburg. | 2007-05-08 |
|
| [Two cases of congenital airway obstruction managed with ex utero intrapartum treatment procedures: anesthetic implications]. | 2007-01 |
|
| Improved migraine management in primary care: results of a patient treatment experience study using zolmitriptan orally disintegrating tablet. | 2006-12 |
|
| Stability of oral liquid preparations of methylergometrine. | 2006-08 |
|
| [Heart and freezer: about one case of hypereosinophilia and coronary spasm]. | 2006-08 |
|
| [Effects of methylergometrine and oxytocin on blood loss and uterine contraction during cesarean section]. | 2006-05 |
|
| [Intraoperative anaphylactic shock induced by methylergometrine and oxytocin]. | 2006-04 |
|
| Clinical characteristics of patients with exercise-induced ST-segment elevation without prior myocardial infarction. | 2006-03 |
|
| [B lynch suture for post partum heamorrhage due to uterine atony]. | 2006-02 |
|
| 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 |
|
| Coronary artery spasm triggered by oral administration of methylergometrine. | 1991-08-03 |
|
| Effect of direct intracoronary administration of methylergonovine in patients with and without variant angina. | 1991-04 |
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
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Edited
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| Record UNII |
5EDH242U9O
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| Record Status |
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| Record Version |
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