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Ergotamine information


Ergotamine
Clinical data
Trade namesCafergot (with caffeine), Ergomar, others
Other names2'-Methyl-5'α-benzyl-12'-hydroxy-3',6',18-trioxoergotaman; 9,10α-Dihydro-12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione
AHFS/Drugs.comMonograph
Routes of
administration
Oral
ATC code
  • N02CA02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class D1 (Drug precursors)[1]
  • CA: Schedule VI
  • UK: POM (Prescription only)
  • US: ℞-only DEA controlled precursor
Pharmacokinetic data
BioavailabilityIntravenous: 100%,[2]
Intramuscular: 47%,[3]
Oral: <1%[4] (Enhanced by co-administration of caffeine[2])
MetabolismHepatic[3]
Elimination half-life2 hours[3]
Excretion90% biliary[3]
Identifiers
IUPAC name
  • (6aR,9R)-N-((2R,5S,10aS,10bS)-5-Benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
  • 113-15-5 checkY
PubChem CID
  • 8223
IUPHAR/BPS
  • 149
DrugBank
  • DB00696 checkY
ChemSpider
  • 7930 checkY
UNII
  • PR834Q503T
KEGG
  • D07906 checkY
ChEBI
  • CHEBI:64318 ☒N
ChEMBL
  • ChEMBL442 checkY
PDB ligand
  • ERM (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID9043774 Edit this at Wikidata
ECHA InfoCard100.003.658 Edit this at Wikidata
Chemical and physical data
FormulaC33H35N5O5
Molar mass581.673 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C
InChI
  • InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1 checkY
  • Key:XCGSFFUVFURLIX-VFGNJEKYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ergotamine, sold under the brand names Cafergot (with caffeine) and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline.[5] It is structurally similar to several neurotransmitters, and it acts as a vasoconstrictor.

It is used for acute migraines, sometimes with caffeine. Medicinal use of ergot fungus began in the 16th century, for the induction of childbirth; but dosage uncertainty discouraged its use. It has been used to prevent post-partum hemorrhage (bleeding after childbirth). It was first isolated from the ergot fungus by Arthur Stoll, at Sandoz in 1918, and was marketed as Gynergen in 1921.[6]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ a b Sanders SW, Haering N, Mosberg H, Jaeger H (1986). "Pharmacokinetics of ergotamine in healthy volunteers following oral and rectal dosing". European Journal of Clinical Pharmacology. 30 (3): 331–334. doi:10.1007/BF00541538. PMID 3732370. S2CID 37538721.
  3. ^ a b c d Tfelt-Hansen P, Johnson ES (1993). "Ergotamine". In Olesen J, Tfelt-Hansen P, Welch KM (eds.). The Headaches. New York: Raven Press. pp. 313–22.
  4. ^ Ibraheem JJ, Paalzow L, Tfelt-Hansen P (December 1983). "Low bioavailability of ergotamine tartrate after oral and rectal administration in migraine sufferers". British Journal of Clinical Pharmacology. 16 (6): 695–699. doi:10.1111/j.1365-2125.1983.tb02243.x. PMC 1428366. PMID 6419759.
  5. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 397–. ISBN 978-3-88763-075-1.
  6. ^ A. J. Giannini, A. E. Slaby. Drugs of Abuse. Oradell, New Jersey: Medical Economics Books, 1989.

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Ergotamine, sold under the brand names Cafergot (with caffeine) and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids;...

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alkaloids is ergotamine, an alkaloid also found in ergot. It acts as a vasoconstrictor and has been reported to control migraines. From ergotamine, the anti-migraine...

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sclerotium contains high concentrations (up to 2% of dry mass) of the alkaloid ergotamine, a complex molecule consisting of a tripeptide-derived cyclol-lactam ring...

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Bellergal is a combination of levorotatory alkaloids of belladonna, ergotamine tartrate, and phenobarbital, used for the treatment of functional menopause...

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Dihydroergotamine

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is an ergot alkaloid used to treat migraines. It is a derivative of ergotamine. It is administered as a nasal spray or injection and has an efficacy...

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ATC code N02

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Dihydroergotamine N02CA02 Ergotamine N02CA04 Methysergide N02CA07 Lisuride N02CA51 Dihydroergotamine, combinations N02CA52 Ergotamine, combinations excluding...

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Nicergoline

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the body, particularly the lungs. Unlike many other ergolines, such as ergotamine, nicergoline is not associated with cardiac fibrosis. It is used for vascular...

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Ergotism

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needed] The dry gangrene is a result of vasoconstriction induced by the ergotamine-ergocristine alkaloids of the fungus.[citation needed] It affects the...

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Serotonin receptor agonist

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migraine and cluster headache attacks. The ergoline antimigraine agent ergotamine also acts on this receptor. Serenics such as batoprazine, eltoprazine...

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Dancing plague of 1518

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which grows commonly on grains (such as rye) used for baking bread. Ergotamine is the main psychoactive product of ergot fungi; it is structurally related...

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Sclerotium

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and reproduction of fungi, as a food source, as medicine (for example, ergotamine), and in agricultural blight management. Examples of fungi that form sclerotia...

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Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide)...

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Rilmenidine

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Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., acetergamine, ergotamine, dihydroergotamine, lisuride, nicergoline, terguride) Etoperidone Fenspiride...

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Fish

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gamma-amanitin, epsilon-amanitin) beta-Nitropropionic acid Citrinin Cytochalasin Ergotamine Fumonisin (Fumonisin B1, Fumonisin B2, Fumonisin B3, Fumonisin B4) Gliotoxin...

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Indole alkaloid

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ergometrinine Water-insoluble polypeptide derivatives: Ergotamine group, including ergotamine, ergosine and their isomers Ergoxine groups, including ergostine...

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Triptan

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which has been marketed since 1991. Triptans have largely replaced ergotamines, an older class of medications used to relieve migraine and cluster headaches...

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Medicinal uses of fungi

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been extracted from or synthesised starting from ergot; these include ergotamine, dihydroergotamine, ergometrine, ergocristine, ergocryptine, ergocornine...

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LSD

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in 1938 from lysergic acid, a chemical derived from the hydrolysis of ergotamine, an alkaloid found in ergot, a fungus that infects grain. LSD was the...

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respiratory depression associated with overdosage of narcotics, and with ergotamine to treat vascular headache. Sodium benzoate is also used in fireworks...

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sclerotium contains high concentrations (up to 2% of dry mass) of the alkaloid ergotamine, a complex molecule consisting of a tripeptide-derived cyclol-lactam ring...

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Another group of CYP3A4 substrates are drugs used for migraine such as ergotamine and dihydroergotamine; their adverse effects may be more pronounced if...

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Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide)...

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Fungus

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viruses and cancer cells. Specific metabolites, such as polysaccharide-K, ergotamine, and β-lactam antibiotics, are routinely used in clinical medicine. The...

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Monoamine oxidase inhibitor

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Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide)...

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