Methylergometrine

Identification

Summary

Methylergometrine is an ergot alkaloid used to prevent and control uterine atony and hemorrhage before and after delivery.

Brand Names
Methergine
Generic Name
Methylergometrine
DrugBank Accession Number
DB00353
Background

A homolog of ergonovine containing one more CH2 group. (Merck Index, 11th ed)

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 339.4314
Monoisotopic: 339.194677059
Chemical Formula
C20H25N3O2
Synonyms
  • 9,10-Didehydro-N-[1-(hydroxymethyl)-propyl]-D-lysergamide
  • D-lysergic acid 1-butanolamide
  • Ergotyl
  • Methylergobasin
  • Methylergometrin
  • Méthylergométrine
  • Methylergometrine
  • Methylergometrinum
  • Methylergonovine
  • Metilergometrina
  • Metilergometrinio
External IDs
  • ME 277

Pharmacology

Indication

For the prevention and control of excessive bleeding following vaginal childbirth

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Methylergometrine is a semisynthetic ergot alkaloid and a derivative of ergonovine and is used for the prevention and control of postpartum and post-abortion hemorrhage. 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.

Mechanism of action

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.

TargetActionsOrganism
ADopamine D1 receptor
antagonist
Humans
U5-hydroxytryptamine receptor 2BNot AvailableHumans
Absorption

Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.

Volume of distribution
  • 56.1 ± 0 L
Protein binding

Not Available

Metabolism

Hepatic, with extensive first-pass metabolism.

Route of elimination

Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver.

Half-life

3.39 hours

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Signs and symptoms of overexposure: hypertension, seizures, headache, hypotension, nausea, and vomiting.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Methylergometrine can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Methylergometrine.
AbirateroneThe metabolism of Methylergometrine can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Methylergometrine.
AcebutololAcebutolol may increase the vasoconstricting activities of Methylergometrine.
AceclofenacThe risk or severity of hypertension can be increased when Methylergometrine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Methylergometrine is combined with Acemetacin.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Methylergometrine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Methylergometrine is combined with Acetylsalicylic acid.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Methylergometrine.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
  • Avoid grapefruit products. Grapefruit inhibits the metabolism of methylergometrine through the CYP3A4 pathway and, therefore, may increase serum levels of methylergometrine. Use caution if co-administering.

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Methylergometrine maleateIR84JPZ1RK57432-61-8NOFOWWRHEPHDCY-DAUURJMHSA-N
Methylergometrine tartrate5EDH242U9O6209-37-6KUTMUWFMKWZQBW-UQJJQXDBSA-N
Product Images
International/Other Brands
Basofortina (Novartis) / Bledstop (Caprifarmindo) / Demergin (Demo) / Ergogin (Cipla) / Ergomed (Medlink) / Ergomin (Alico Impex) / Ergotyl (Sandoz) / Expogin (L.B.S.) / Glomethyl (Metiska) / Ingagen-M (Inga) / Mem (Elin) / Mergot (Lloyd) / Mergotrex (Rotexmedica) / Metenarin / Metermin (Cadila) / Méthergin (Novartis) / Methergin (Novartis) / Metherinal (Landson) / Metherspan (Opsonin) / Methovin (Kimia Farma) / Methylergobrevin (Hemofarm) / Methylergometrin (Spofa) / Metilat (Metiska) / Metiler (Adeka) / Metilergometrina (Hospira Italia) / Metrine (T P Drug) / Metrol (Simed) / Metvell (Novell) / Myomergin (Ethica Industri Farmasi) / Myometril (Oriental Chemical Works) / Neo-ergo (Oriental) / Partan M (Mochida) / Pospargin (Kalbe) / Satergin (Tablets) / Usamema (Icon) / Utergin (Svizera) / Uterine (LBS) / Uterjin (Münir Sahin) / Uterowin (Bestochem) / Utesel (Osel)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MethergineTablet, coated0.2 mg/1Oralbryant ranch prepack1946-11-19Not applicableUS flag63629 379120180907 15195 flsol
MethergineTablet, coated0.2 mg/1OralDispensing Solutions, Inc.1946-11-19Not applicableUS flag66336 040220210331 17394 1wdtd1
MethergineTablet, coated0.2 mg/1OralPd Rx Pharmaceuticals, Inc.1946-11-192016-04-13US flag00078 0054 05 nlmimage10 e208f107
MethergineTablet, coated0.2 mg/1OralNovartis1946-11-192013-04-01US flag0078 005420180907 15195 1fd9mbi
MethergineTablet, coated0.2 mg/1OralApotheca, Inc.2006-12-27Not applicableUS flag12634 017920210321 24370 1y5jyft
MethergineInjection, solution0.2 mg/1mLIntramuscular; IntravenousNovartis2002-01-282015-03-01US flag
MethergineTablet, coated0.2 mg/1OralPhysicians Total Care, Inc.1946-11-192007-06-30US flag
MethergineTablet, coated0.2 mg/1OralPd Rx Pharmaceuticals, Inc.1946-11-192016-04-13US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MethergineTablet0.2 mg/1OralLupin Pharmaceuticals, Inc.2016-04-04Not applicableUS flag
MethergineTablet0.2 mg/1OralAvera McKennan Hospital2016-06-232017-05-24US flag
Methylergonovine MaleateTablet0.2 mg/1OralPD-Rx Pharmaceuticals, Inc.2011-08-012018-08-21US flag
Methylergonovine MaleateTablet0.2 mg/1OralAtlantic Biologicals Corp.2019-03-26Not applicableUS flag
Methylergonovine MaleateInjection, solution0.2 mg/1mLIntramuscular; IntravenousAMERICAN REGENT, INC.2010-06-21Not applicableUS flag
Methylergonovine MaleateTablet0.2 mg/1OralRising Pharma Holdings, Inc.2021-01-15Not applicableUS flag
Methylergonovine MaleateTablet0.2 mg/1OralAmneal Pharmaceuticals NY LLC2018-09-12Not applicableUS flag
Methylergonovine MaleateTablet0.2 mg/1OralKAISER FOUNDATION HOSPITALS2012-05-312013-05-31US flag
Methylergonovine MaleateTablet0.2 mg/1OralWest-Ward Pharmaceuticals Corp2018-07-03Not applicableUS flag
Methylergonovine MaleateTablet0.2 mg/1OralAmerincan Health Packaging2012-05-012016-04-30US flag43386 0140 28 nlmimage10 2d3c96b4

Categories

ATC Codes
G02AC01 — Methylergometrine and oxytocinG02AB01 — Methylergometrine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Ergoline and derivatives
Sub Class
Lysergic acids and derivatives
Direct Parent
Lysergamides
Alternative Parents
Indoloquinolines / Benzoquinolines / Quinoline-3-carboxamides / Pyrroloquinolines / 3-alkylindoles / Isoindoles and derivatives / Aralkylamines / Benzenoids / Heteroaromatic compounds / Pyrroles
show 9 more
Substituents
3-alkylindole / Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoquinoline / Carbonyl group
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
W53L6FE61V
CAS number
113-42-8
InChI Key
UNBRKDKAWYKMIV-QWQRMKEZSA-N
InChI
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
IUPAC Name
(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
SMILES
[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO

References

General References
Not Available
Human Metabolome Database
HMDB0014497
KEGG Drug
D00680
PubChem Compound
8226
PubChem Substance
46507746
ChemSpider
7933
BindingDB
50330860
RxNav
6883
ChEBI
92607
ChEMBL
CHEMBL1201356
ZINC
ZINC000095619105
Therapeutic Targets Database
DAP000978
PharmGKB
PA450461
PDBe Ligand
H8D
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Methylergometrine
PDB Entries
6dry
MSDS
Download (42.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionBloodloss / Postpartum Haemorrhage (PPH)1
4CompletedPreventionHemorrhage1
4CompletedPreventionUterine Atony With Hemorrhage1
4CompletedTreatmentAnemia / Bleeding1
4CompletedTreatmentHypotension / Uterine Atony1
4RecruitingTreatmentPostpartum Haemorrhage (PPH) / Uterine Atony1
1CompletedPreventionCesarean Sections1
0WithdrawnTreatmentPostpartum Haemorrhage (PPH) / Uterine Atony / Uterine tone disorders1
Not AvailableCompletedPreventionEndometritis1

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
  • Pharmaforce inc
Packagers
  • American Regent
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • C.B. Fleet Co. Inc.
  • Cardinal Health
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • Novartis AG
  • Pharmaforce Inc.
  • Physicians Total Care Inc.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
Dosage Forms
FormRouteStrength
Injection
Tablet, sugar coatedOral
Injection, solutionIntramuscular
Solution0.2 mg/1ml
Injection, solutionParenteral0.2 MG/ML
Solution / dropsOral0.25 MG/ML
Tablet, coatedOral0125 MG
SolutionIntramuscular; Intravenous0.2 mg
Injection, solutionIntramuscular; Intravenous0.2 mg/1mL
Tablet, coatedOral0.2 mg/1
InjectionIntramuscular; Intravenous0.2 mg/1mL
InjectionIntravenous0.2 mg/1mL
TabletOral0.2 mg/1
Solution / dropsOral
SolutionOral
Tablet, coatedOral
Injection, solution
Tablet, film coatedOral
Tablet, film coatedOral0.125 MG
SolutionIntramuscular; Intravenous
SolutionIntramuscular
Prices
Unit descriptionCostUnit
Methergine 0.2 mg/ml ampul7.81USD ml
Methylergonovine 0.2 mg/ml vial5.28USD ml
Methergine 0.2 mg tablet1.42USD tablet
Norforms fem deodorant suppository0.29USD suppository
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)172 °CPhysProp
water solubility25 mg/mLNot Available
logP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.204 mg/mLALOGPS
logP1.74ALOGPS
logP1.59ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15ChemAxon
pKa (Strongest Basic)7.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area68.36 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.58 m3·mol-1ChemAxon
Polarizability38.73 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.6556
Caco-2 permeable-0.8726
P-glycoprotein substrateSubstrate0.8604
P-glycoprotein inhibitor INon-inhibitor0.874
P-glycoprotein inhibitor IINon-inhibitor0.8959
Renal organic cation transporterNon-inhibitor0.7798
CYP450 2C9 substrateNon-substrate0.8316
CYP450 2D6 substrateNon-substrate0.8979
CYP450 3A4 substrateSubstrate0.664
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8641
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8959
Ames testNon AMES toxic0.5734
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.8422
Rat acute toxicity3.5304 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9614
hERG inhibition (predictor II)Inhibitor0.5889
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Reyes FD, Mozzachiodi R, Baxter DA, Byrne JH: Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. Learn Mem. 2005 May-Jun;12(3):216-20. [Article]
  4. Nargeot R, Baxter DA, Patterson GW, Byrne JH: Dopaminergic synapses mediate neuronal changes in an analogue of operant conditioning. J Neurophysiol. 1999 Apr;81(4):1983-7. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
Gene Name
HTR2B
Uniprot ID
P41595
Uniprot Name
5-hydroxytryptamine receptor 2B
Molecular Weight
54297.41 Da
References
  1. Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL: Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications. Circulation. 2000 Dec 5;102(23):2836-41. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Moubarak AS, Rosenkrans CF Jr, Johnson ZB: Modulation of cytochrome P450 metabolism by ergonovine and dihydroergotamine. Vet Hum Toxicol. 2003 Feb;45(1):6-9. [Article]

Drug created on June 13, 2005 13:24 / Updated on August 07, 2021 00:20