methylergometrine

Small moleculeapproved

Approved

Nov 19, 1946

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. — NCATS

Clinical trial activity

5 trials · 5 clinical orgs · 14 marketing orgs

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
3

Earliest trial started Jun 1, 2005 (NCT00481533)

Timeline

1940s

  1. Nov 19, 1946

    Earliest FDA Approval

  2. Nov 19, 1946

    Bioelectron — NDA Secondary Org

2000s

  1. Nov 24, 2008

    Sankyo — Marketing Organization

  2. Nov 24, 2008

    Lutipold — Marketing Organization

  3. Nov 24, 2008

    Daiichi Sankyo — Marketing Organization

2010s

  1. Sep 13, 2010

    Esteve Labs — Marketing Organization

  2. May 2, 2011

    Novel Anti-Infective Technologies, LLC — Marketing Organization

  3. May 2, 2011

    Chartwell Pharmaceuticals — Marketing Organization

  4. May 15, 2018

    Granules India — Marketing Organization

  5. Sep 10, 2018

    Amneal Pharmaceuticals — Marketing Organization

  6. Mar 20, 2019

    Teva — Marketing Organization

2020s

  1. May 1, 2020

    Tulex Pharmaceuticals — Marketing Organization

  2. May 1, 2020

    TRUPHARMA — Marketing Organization

  3. Jan 15, 2021

    Rising Pharmaceuticals — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedNov 19, 1946

Chemistry & pharmacology

Loading structure…

SMILES

CC[C@@H](CO)NC(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1
Mol. weight
339.44 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

No

Sources

Also known as

  • 9,10-didehydro-n-[1-(hydroxymethyl)-propyl]-d-lysergamide
  • 9,10-didehydro-n-[1-(hydroxymethyl)-propyl]-d-lysergamide
  • d-lysergic acid 1-butanolamide
  • d-lysergic acid 1-butanolamide
  • ergotyl
  • ergotyl
  • methergen
  • methergine
  • methergine
  • methergine
  • methergine
  • methergine
  • methergine
  • methylergobasin
  • methylergobasin
  • methylergobasin
  • methylergobasine
  • methylergobrevin
  • methylergometrin
  • methylergometrin
  • methylergometrin
  • methylergometrine
  • methylergometrine
  • methylergometrine
  • methylergometrine
  • methylergometrine
  • methylergometrine
  • méthylergométrine
  • méthylergométrine
  • methylergometrine maleate
  • methylergometrine maleate
  • methylergometrine maleate
  • methylergometrine maleate
  • methylergometrine maleate
  • methylergometrine maleate
  • methylergometrinum
  • methylergometrinum
  • methylergonovine
  • methylergonovine
  • methylergonovine
  • methylergonovine
  • methylergonovine
  • methylergonovine
  • methylergonovine
  • methylergonovine maleate
  • methylergonovine maleate
  • methylergonovine maleate
  • methylergonovine maleate
  • methylergonovinium bimaleate
  • methylergonovinium bimaleate
  • metilergometrina
  • metilergometrina
  • partergin

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT03584854Phase 4Jul 31, 2018Harvard University
NCT02408965Phase 4Mar 1, 2015University of California, San Francisco
NCT02101567Phase 4May 1, 2014Beni Suef University
NCT00858832N/ADec 1, 2008University of South Florida
NCT00481533N/AJun 1, 2005Icahn School of Medicine at Mount Sinai
Showing 5 of 5 trials
Page 1 / 1

Organizations

Research & Development (5)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Beni Suef UniversityAcademic/Hospital1112014
Harvard UniversityAcademic/Hospital1112018
Icahn School of Medicine at Mount SinaiAcademic/Hospital1112005
University of California, San FranciscoAcademic/Hospital1112015
University of South FloridaAcademic/Hospital1112008
5 organizations
Page 1 / 1

Marketing (16)

OrganizationOrg typeRelationshipDate
Amneal PharmaceuticalsFor profitMKTGSep 10, 2018
BioelectronFor profitNDA2Nov 19, 1946
Chartwell PharmaceuticalsFor profitMKTGMay 2, 2011
Daiichi SankyoFor profitMKTGNov 24, 2008
Esteve LabsFor profitSYNSep 13, 2010
Esteve LabsFor profitMKTGSep 13, 2010
Granules IndiaFor profitMKTGMay 15, 2018
Granules IndiaFor profitSYNMay 15, 2018
LutipoldFor profitMKTGNov 24, 2008
Novel Anti-Infective Technologies, LLCFor profitMKTGMay 2, 2011
Rising PharmaceuticalsFor profitMKTGJan 15, 2021
SandozFor profitNDA
SankyoFor profitMKTGNov 24, 2008
TRUPHARMAFor profitMKTGMay 1, 2020
TevaFor profitMKTGMar 20, 2019
Tulex PharmaceuticalsFor profitMKTGMay 1, 2020