Ergotamine

Ergotamine
Clinical data
Trade names	Ergomar, others
Other names	2'-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.com	Monograph
License data	US DailyMed: Ergotamine;
Pregnancy; category	AU: C; US: Contraindicated;
Routes of; administration	Oral
ATC code	N02CA02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class D1 (Drug precursors); CA: Schedule VI; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	Intravenous: 100%, ; Intramuscular: 47%,; Oral: <1% (Enhanced by co-administration of caffeine)
Metabolism	Liver
Elimination half-life	2 hours
Excretion	90% Bile duct
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 ;
PubChem CID	8223;
IUPHAR/BPS	149;
DrugBank	DB00696 ;
ChemSpider	7930 ;
UNII	PR834Q503T;
KEGG	D07906 ;
ChEBI	CHEBI:64318 ;
ChEMBL	ChEMBL442 ;
PDB ligand	ERM (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID9043774 ;
ECHA InfoCard	100.003.658
Chemical and physical data
Formula	C33H35N5O5
Molar mass	581.673 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 ; Key:XCGSFFUVFURLIX-VFGNJEKYSA-N ;
	(what is this?) (verify)

Ergotamine, sold under the brand name Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline.^[9] It is structurally similar to several neurotransmitters, and it acts as a vasoconstrictor. It is used for acute migraines, sometimes with caffeine as the combination ergotamine/caffeine.^[10]^[11]

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.^[12]

^ "Prescribing medicines in pregnancy database". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 20 May 2024.
^ ^a ^b "Ergomar- ergotamine tartrate tablet, orally disintegrating". DailyMed. 8 September 2012. Retrieved 20 May 2024.
^ "Ergotamine (Ergomar) Use During Pregnancy". Drugs.com. 6 May 2024. Retrieved 20 May 2024.
^ Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
^ "Ergomar sublingual- ergotamine tartrate tablet". DailyMed. 25 October 2022. Retrieved 18 May 2024.
^ ^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.
^ ^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.
^ 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.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 397–. ISBN 978-3-88763-075-1.
^ "Cafergot- ergotamine tartrate and caffeine tablet, film coated". DailyMed. U.S. National Library of Medicine. Archived from the original on 16 January 2014.
^ "Migergot- ergotamine tartrate and caffeine suppository". DailyMed. 29 November 2022. Retrieved 18 May 2024.
^ A. J. Giannini, A. E. Slaby. Drugs of Abuse. Oradell, New Jersey: Medical Economics Books, 1989.

[1] "Prescribing medicines in pregnancy database". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 20 May 2024.

[Ergomar_FDA_label-2] "Ergomar- ergotamine tartrate tablet, orally disintegrating". DailyMed. 8 September 2012. Retrieved 20 May 2024.

[3] "Ergotamine (Ergomar) Use During Pregnancy". Drugs.com. 6 May 2024. Retrieved 20 May 2024.

[4] Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.

[Ergomar_sublingual_FDA_label-5] "Ergomar sublingual- ergotamine tartrate tablet". DailyMed. 25 October 2022. Retrieved 18 May 2024.

[kinetics1-6] 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.

[kinetics2-7] 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.

[pmid6419759-8] 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.

[IndexNominum2000-9] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 397–. ISBN 978-3-88763-075-1.

[Cafergot_FDA_label-10] "Cafergot- ergotamine tartrate and caffeine tablet, film coated". DailyMed. U.S. National Library of Medicine. Archived from the original on 16 January 2014.

[Migergot_FDA_label-11] "Migergot- ergotamine tartrate and caffeine suppository". DailyMed. 29 November 2022. Retrieved 18 May 2024.

[12] A. J. Giannini, A. E. Slaby. Drugs of Abuse. Oradell, New Jersey: Medical Economics Books, 1989.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]