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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N3O2
Molecular Weight 339.4314
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLERGONOVINE

SMILES

CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1

InChI

InChIKey=UNBRKDKAWYKMIV-QWQRMKEZSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H25N3O2
Molecular Weight 339.4314
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
21.38 nM [EC50]
0.49 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
METHERGINE

Cmax

ValueDoseCo-administeredAnalytePopulation
5918 pg/mL
0.2 mg single, intramuscular
METHYLERGONOVINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
13889 pg × h/mL
0.2 mg single, intramuscular
METHYLERGONOVINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.39 h
0.2 mg single, intramuscular
METHYLERGONOVINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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
Unknown
Substance Class Chemical
Record UNII
W53L6FE61V
Record Status Validated (UNII)
Record Version