QuickView for Ergotamine (compound)

Summary
General Info

PubChem

PubChem Compound 115248

Name:	Ergotamine
PubChem Compound ID:	115248
Description:	A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.
Molecular formula:	C₃₃H₃₅N₅O₅
Molecular weight:	581.662 g/mol
Synonyms:	Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha,8alpha)-; Ergotaminine; Isoergotamine; 639-81-6

DrugBank

Identification

Name:	Ergotamine
Name (isomeric):	DB00696
Drug Type:	small molecule
Description:	A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.
Brand:	Ergomar, Ergoton-A, Medihaler Ergotamine, Ergostat, Wigrettes, Ergotamin
Brand name mixture:	Wigraine Suppositories(Belladonna + Caffeine + Ergotamine Tartrate), Gravergol Capsules(Caffeine + Dimenhydrinate + Ergotamine Tartrate), Cafergot Tab(Caffeine + Ergotamine Tartrate), Cafergot Pb Tab(Belladonna + Caffeine + Ergotamine (Ergotamine Tartrate) + Pentobarbital Sodium), Cafergot Sup(Caffeine + Ergotamine Tartrate), Cafergot Pb Sup(Bel... show more » Wigraine Suppositories(Belladonna + Caffeine + Ergotamine Tartrate), Gravergol Capsules(Caffeine + Dimenhydrinate + Ergotamine Tartrate), Cafergot Tab(Caffeine + Ergotamine Tartrate), Cafergot Pb Tab(Belladonna + Caffeine + Ergotamine (Ergotamine Tartrate) + Pentobarbital Sodium), Cafergot Sup(Caffeine + Ergotamine Tartrate), Cafergot Pb Sup(Belladonna + Caffeine + Ergotamine (Ergotamine Tartrate) + Pentobarbital), Bellergal Tab(Belladonna + Ergotamine (Ergotamine Tartrate) + Phenobarbital), Bellergal Spacetabs(Belladonna + Ergotamine Tartrate + Phenobarbital), Ergodryl Cap(Caffeine Citrate + Diphenhydramine Hydrochloride + Ergotamine Tartrate), Megral Tabs(Caffeine + Cyclizine Hydrochloride + Ergotamine Tartrate), Wigraine Tab(Belladonna + Caffeine + Ergotamine Tartrate) show less «
Category:	Sympatholytics, Adrenergic alpha-Agonists, Analgesics, Non-Narcotic, Vasoconstrictor Agents
CAS number:	113-15-5

Pharmacology

Indication:	For use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called "histaminic cephalalgia".
Pharmacology:	Ergotamine is a vasoconstrictor and alpha adrenoreceptor antagonist. The pharmacological properties of ergotamine are extremely complex; some of its actions are unrelated to each other, and even mutually antagonistic. The drug has partial agonist and/or antagonist activity against tryptaminergic, dopaminergic and alpha adrenergic receptors dependin... show more » Ergotamine is a vasoconstrictor and alpha adrenoreceptor antagonist. The pharmacological properties of ergotamine are extremely complex; some of its actions are unrelated to each other, and even mutually antagonistic. The drug has partial agonist and/or antagonist activity against tryptaminergic, dopaminergic and alpha adrenergic receptors depending upon their site, and it is a highly active uterine stimulant. It causes constriction of peripheral and cranial blood vessels and produces depression of central vasomotor centers. The pain of a migraine attack is believed to be due to greatly increased amplitude of pulsations in the cranial arteries, especially the meningeal branches of the external carotid artery. Ergotamine reduces extracranial blood flow, causes a decline in the amplitude of pulsation in the cranial arteries, and decreases hyperperfusion of the territory of the basilar artery. It does not reduce cerebral hemispheric blood flow. show less «
Mechanism of Action:	Ergotamine acts on migraine by one of two proposed mechanisms: 1) activation of 5-HT_1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache, and 2) activation of 5-HT_1D receptors on sensory nerve endings ... show more » Ergotamine acts on migraine by one of two proposed mechanisms: 1) activation of 5-HT_1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache, and 2) activation of 5-HT_1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release. show less «
Absorption:	The bioavailability of sublingually administered ergotamine has not been determined.
Biotransformation:	Hepatic. Ergotamine is metabolized by the liver by largely undefined pathways, and 90% of the metabolites are excreted in the bile.
Half Life:	2 hours
Toxicity:	Signs of overexposure include irritation, nausea, vomiting, headache, diarrhea, thirst, coldness of skin, pruritus, weak pulse, numbness, tingling of extremities, and confusion.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Caffeine increases absorption.

Take without regard to meals.

Drug interaction:

Rizatriptan	Possible severe and prolonged vasoconstriction
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Betaxolol	Ischemia with risk of gangrene
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Zileuton	Possible ergotism and severe ischemia with this combination

Rizatriptan	Possible severe and prolonged vasoconstriction
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Betaxolol	Ischemia with risk of gangrene
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Zileuton	Possible ergotism and severe ischemia with this combination
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Isosorbide Mononitrate	Possible antagonism of action
Labetalol	Ischemia with risk of gangrene
Penbutolol	Ischemia with risk of gangrene
Amprenavir	Amprenavir may increase the effect and toxicity of ergotamine.
Sumatriptan	Possible severe and prolonged vasoconstriction
Ritonavir	The protease inhibitor, ritonavir, may increase the effect and toxicity of the ergot derivative, ergotamine.
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Esmolol	Ischemia with risk of gangrene
Efavirenz	The antiretroviral agent may increase the ergot derivative toxicity
Metoprolol	Ischemia with risk of gangrene
Indinavir	Indinavir may increase the serum concentration of ergotamine. Concomitant therapy is contraindicated.
Nefazodone	Possible ergotism and severe ischemia with this combination
Sotalol	Ischemia with risk of gangrene
Eletriptan	Possible severe and prolonged vasoconstriction
Practolol	Ischemia with risk of gangrene
Fluconazole	Possible ergotism and severe ischemia with this combination
Timolol	Ischemia with risk of gangrene
Telithromycin	Telithromycin may reduce clearance of Ergotamine. Concomitant therapy is contraindicated.
Isosorbide Dinitrate	Possible antagonism of action
Posaconazole	Contraindicated co-administration
Pentaerythritol Tetranitrate	Possible antagonism of action
Frovatriptan	Possible severe and prolonged vasoconstriction
Fosamprenavir	Amprenavir increases the effect and toxicity of ergot derivative
Acebutolol	Ischemia with risk of gangrene
Zolmitriptan	Concomitant use of the serotonin 5-HT1D receptor agonist, zolmitriptan, and the ergot derivative, ergotamine, may result in additive vasoconstrictive effects. Concomitant use within 24 hours is contraindicated.
Nadolol	Ischemia with risk of gangrene
Atenolol	Ischemia with risk of gangrene
Tipranavir	Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Ergotamine. Concomitant therapy is contraindicated.
Fluvoxamine	Possible ergotism and severe ischemia with this combination
Almotriptan	Possible severe and prolonged vasoconstriction
Delavirdine	The antiretroviral agent may increase the ergot derivative toxicity
Amyl Nitrite	Possible antagonism of action
Fluoxetine	Possible ergotism and severe ischemia with this combination
Erythromycin	Possible ergotism and severe ischemia with this combination
Carteolol	Ischemia with risk of gangrene
Clarithromycin	Risk of ergotism and severe ischemia with this association
Troleandomycin	Possible ergotism and severe ischemia with this combination
Bisoprolol	Ischemia with risk of gangrene
Venlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Naratriptan	Possible severe and prolonged vasoconstriction.
Nitroglycerin	Possible antagonism of action
Ketoconazole	Possible ergotism and severe ischemia with this combination.
Sibutramine	Possible serotoninergic syndrome with this combination
Itraconazole	Possible ergotism and severe ischemia with this combination
Josamycin	Possible ergotism and severe ischemia with this combination
Propranolol	Ischemia with risk of gangrene
Desvenlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Oxprenolol	Ischemia with risk of gangrene
Nelfinavir	Nelfinavir increases the effect and toxicity of ergot derivative
Saquinavir	The protease inhibitor, saquinavir, may increase the effect and toxicity of the ergot derivative, ergotamine.
Pindolol	Ischemia with risk of gangrene
Bevantolol	Ischemia with risk of gangrene
Erythrityl Tetranitrate	Possible antagonism of action
Carvedilol	Ischemia with risk of gangrene
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of ergotamine by decreasing its metabolism. Concomitant therapy is contraindicated.
Atazanavir	Atazanavir may increase the effect and toxicity of ergotamine.

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Targets

5-hydroxytryptamine 1D receptor

5-hydroxytryptamine 1B receptor

5-hydroxytryptamine 2A receptor

D(2) dopamine receptor

Alpha-1A adrenergic receptor

Alpha-1B adrenergic receptor

Alpha-1D adrenergic receptor

Alpha-2A adrenergic receptor

Alpha-2B adrenergic receptor

Sodium-dependent noradrenaline transporter

Enzymes

Cytochrome P450 3A4

Cytochrome P450 1A2

Transporters

Multidrug resistance protein 1