methylergometrine
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
Earliest trial started Jun 1, 2005 (NCT00481533)
Timeline
1940s
- Nov 19, 1946
Earliest FDA Approval
- Nov 19, 1946
Bioelectron — NDA Secondary Org
2000s
- Nov 24, 2008
Sankyo — Marketing Organization
- Nov 24, 2008
Lutipold — Marketing Organization
- Nov 24, 2008
Daiichi Sankyo — Marketing Organization
2010s
- Sep 13, 2010
Esteve Labs — Marketing Organization
- May 2, 2011
Novel Anti-Infective Technologies, LLC — Marketing Organization
- May 2, 2011
Chartwell Pharmaceuticals — Marketing Organization
- May 15, 2018
Granules India — Marketing Organization
- Sep 10, 2018
Amneal Pharmaceuticals — Marketing Organization
- Mar 20, 2019
Teva — Marketing Organization
2020s
- May 1, 2020
Tulex Pharmaceuticals — Marketing Organization
- May 1, 2020
TRUPHARMA — Marketing Organization
- Jan 15, 2021
Rising Pharmaceuticals — Marketing Organization
Indications
Approved for
Mechanism of action
- Dopamine D1 receptorANTAGONIST
DRD1 antagonist
- Serotonin 2b (5-HT2b) receptorPARTIAL AGONIST
HTR2B partial agonist
Approval history
- approvedNov 19, 1946
Chemistry & pharmacology
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
- ChEMBLCHEMBL1201356 ↗
- WikipediaMethylergometrine ↗
- NCATSW53L6FE61V ↗
- ChEMBLCHEMBL1200843 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT03584854 | Phase 4 | Jul 31, 2018 | Harvard University |
| NCT02408965 | Phase 4 | Mar 1, 2015 | University of California, San Francisco |
| NCT02101567 | Phase 4 | May 1, 2014 | Beni Suef University |
| NCT00858832 | N/A | Dec 1, 2008 | University of South Florida |
| NCT00481533 | N/A | Jun 1, 2005 | Icahn School of Medicine at Mount Sinai |
Organizations
Research & Development (5)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Beni Suef University | Academic/Hospital | 1 | 1 | 1 | 2014 |
| Harvard University | Academic/Hospital | 1 | 1 | 1 | 2018 |
| Icahn School of Medicine at Mount Sinai | Academic/Hospital | 1 | 1 | 1 | 2005 |
| University of California, San Francisco | Academic/Hospital | 1 | 1 | 1 | 2015 |
| University of South Florida | Academic/Hospital | 1 | 1 | 1 | 2008 |
Marketing (16)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Amneal Pharmaceuticals | For profit | MKTG | Sep 10, 2018 |
| Bioelectron | For profit | NDA2 | Nov 19, 1946 |
| Chartwell Pharmaceuticals | For profit | MKTG | May 2, 2011 |
| Daiichi Sankyo | For profit | MKTG | Nov 24, 2008 |
| Esteve Labs | For profit | SYN | Sep 13, 2010 |
| Esteve Labs | For profit | MKTG | Sep 13, 2010 |
| Granules India | For profit | MKTG | May 15, 2018 |
| Granules India | For profit | SYN | May 15, 2018 |
| Lutipold | For profit | MKTG | Nov 24, 2008 |
| Novel Anti-Infective Technologies, LLC | For profit | MKTG | May 2, 2011 |
| Rising Pharmaceuticals | For profit | MKTG | Jan 15, 2021 |
| Sandoz | For profit | NDA | — |
| Sankyo | For profit | MKTG | Nov 24, 2008 |
| TRUPHARMA | For profit | MKTG | May 1, 2020 |
| Teva | For profit | MKTG | Mar 20, 2019 |
| Tulex Pharmaceuticals | For profit | MKTG | May 1, 2020 |