QuickView for Methylergonovine (compound)

Summary
General Info

PubChem

PubChem Compound 114724

Name:	Methylergonovine
PubChem Compound ID:	114724
Description:	A homolog of ERGONOVINE containing one more CH2 group. (Merck Index, 11th ed)
Molecular formula:	C₂₀H₂₅N₃O₂
Molecular weight:	339.432 g/mol
Synonyms:	20313-98-8

DrugBank

Identification

Name:	Methylergonovine
Name (isomeric):	DB00353
Drug Type:	small molecule
Description:	A homolog of ERGONOVINE containing one more CH2 group. (Merck Index, 11th ed)
Synonyms:	Methylergobrevin; Methylergobasine; Methylergobasin; Methylergonovin; methylergonovine maleate; Methylergometrine; Methylergometrin
Brand:	Norforms, Spametrin-M, Metenarin, Methergen, Partergin, Basofortina, Methergine, Methergin, Ryegonovin
Category:	Oxytocics
CAS number:	113-42-8

Pharmacology

Indication:	For the prevention and control of excessive bleeding following vaginal childbirth
Pharmacology:	Methylergonovine 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.... show more » Methylergonovine 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. show less «
Mechanism of Action:	Methylergonovine 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.
Absorption:	Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.
Biotransformation:	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
Toxicity:	Signs and symptoms of overexposure: hypertension, seizures, headache, hypotension, nausea, and vomiting.
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Delavirdine	The antiretroviral agent may increase the ergot derivative toxicity
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Erythromycin	Possible ergotism and severe ischemia with this combination
Epinephrine	Possible marked increase of arterial pressure

Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Delavirdine	The antiretroviral agent may increase the ergot derivative toxicity
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Erythromycin	Possible ergotism and severe ischemia with this combination
Epinephrine	Possible marked increase of arterial pressure
Eletriptan	Possible severe and prolonged vasoconstriction
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Isosorbide Mononitrate	Possible antagonism of action
Atazanavir	Increases the effect and toxicity of ergot derivative
Telithromycin	Telithromycin may reduce clearance of Methylergonovine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Methylergonovine if Telithromycin is initiated, discontinued or dose changed.
Phenylephrine	Possible marked increase of arterial pressure
Isosorbide Dinitrate	Possible antagonism of action
Venlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Zolmitriptan	Concomitant use of the serotonin 5-HT1D receptor agonist, zolmitriptan, and the ergot derivative, methylergonovine, may result in additive vasoconstrictive effects. Concomitant use within 24 hours is contraindicated.
Pentaerythritol Tetranitrate	Possible antagonism of action
Nitroglycerin	Possible antagonism of action
Frovatriptan	Possible severe and prolonged vasoconstriction
Naratriptan	Possible severe and prolonged vasocontriction
Tipranavir	Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Methylergonovine. Concomitant therapy is contraindicated.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of methylergonovine by decreasing its metabolism. Concomitant therapy is contraindicated.
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Efavirenz	The antiretroviral agent may increase the ergot derivative toxicity
Desvenlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Almotriptan	Possible severe and prolonged vasoconstriction

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Targets

D(1A) dopamine receptor

Enzymes

Cytochrome P450 3A4