Editing Ergotamine (section)

{{Short description|Chemical compound in the ergot family of alkaloids}}
{{Use dmy dates|date=May 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443732840
| image = Ergotamine-skeletal.svg
| width = 250
| alt = 
| image2 = Ergotamine ball-and-stick.png
| width2 =
| alt2 = 

<!-- Clinical data -->
| pronounce = 
| tradename = Ergomar, others
| Drugs.com = {{drugs.com|monograph|ergotamine}}
| MedlinePlus = 
| DailyMedID = Ergotamine
| pregnancy_AU = C
| pregnancy_AU_comment = <ref>{{cite web | title=Prescribing medicines in pregnancy database | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/products/medicines/find-information-about-medicine/prescribing-medicines-pregnancy-database | access-date=20 May 2024}}</ref>
| pregnancy_category = US: Contraindicated<ref name="Ergomar FDA label" /><ref>{{cite web | title=Ergotamine (Ergomar) Use During Pregnancy | website=Drugs.com | date=6 May 2024 | url=https://www.drugs.com/pregnancy/ergotamine.html | access-date=20 May 2024}}</ref>
| routes_of_administration = [[Oral administration|Oral]]
| class = 
| ATC_prefix = N02
| ATC_suffix = CA02
| ATC_supplemental = 

<!-- Legal status -->
| legal_AU = Schedule 4
| legal_AU_comment = 
| legal_BR = D1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=15 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA = Schedule VI
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = 
| legal_US = Rx-only
| legal_US_comment = <ref name="Ergomar FDA label">{{cite web | title=Ergomar- ergotamine tartrate tablet, orally disintegrating | website=DailyMed | date=8 September 2012 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1bfd4827-5123-4dbb-8f94-7b097f5bfd5c | access-date=20 May 2024}}</ref><ref name="Ergomar sublingual FDA label">{{cite web | title=Ergomar sublingual- ergotamine tartrate tablet | website=DailyMed | date=25 October 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=dac9637f-3326-4f25-b7b9-f9f54b738232 | access-date=18 May 2024}}</ref>
| legal_EU = 
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = Intravenous: 100%,<ref name="kinetics1">{{cite journal | vauthors = Sanders SW, Haering N, Mosberg H, Jaeger H | title = Pharmacokinetics of ergotamine in healthy volunteers following oral and rectal dosing | journal = European Journal of Clinical Pharmacology | volume = 30 | issue = 3 | pages = 331–334 | date = 1986 | pmid = 3732370 | doi = 10.1007/BF00541538 | s2cid = 37538721 }}</ref> <br />Intramuscular: 47%,<ref name="kinetics2">{{cite book | vauthors = Tfelt-Hansen P, Johnson ES | chapter = Ergotamine | veditors = Olesen J, Tfelt-Hansen P, Welch KM | title = The Headaches | location = New York | publisher = Raven Press | date = 1993 | pages = 313–22 }}</ref><br />Oral: <1%<ref name="pmid6419759">{{cite journal | vauthors = Ibraheem JJ, Paalzow L, Tfelt-Hansen P | title = Low bioavailability of ergotamine tartrate after oral and rectal administration in migraine sufferers | journal = British Journal of Clinical Pharmacology | volume = 16 | issue = 6 | pages = 695–699 | date = December 1983 | pmid = 6419759 | pmc = 1428366 | doi = 10.1111/j.1365-2125.1983.tb02243.x }}</ref> (Enhanced by co-administration of caffeine<ref name="kinetics1" />)
| protein_bound = 
| metabolism = [[Liver]]<ref name="kinetics2" />
| metabolites = 
| onset = 
| elimination_half-life = 2 hours<ref name="kinetics2" />
| duration_of_action = 
| excretion = 90% [[Bile duct]]<ref name="kinetics2" />

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 113-15-5
| CAS_supplemental = 
| PubChem = 8223
| IUPHAR_ligand = 149
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00696
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7930
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PR834Q503T
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07906
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 64318
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 442
| NIAID_ChemDB = 
| PDB_ligand = ERM
| synonyms = 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

<!-- Chemical data -->
| IUPAC_name = (6a''R'',9''R'')-''N''-((2''R'',5''S'',10a''S'',10b''S'')-5-Benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2''H''-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
| C=33 | H=35 | N=5 | O=5
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XCGSFFUVFURLIX-VFGNJEKYSA-N

<!-- Physical data -->
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}

'''Ergotamine''', sold under the brand name '''Ergomar''' among others, is an [[ergopeptine]] and part of the [[ergot]] family of [[alkaloid]]s; it is structurally and biochemically closely related to [[ergoline]].<ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA397|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=397–}}</ref> It is structurally similar to several [[neurotransmitter]]s, and it [[biological activity|acts]] as a [[vasoconstrictor]]. It is used for acute [[migraine]]s, sometimes with [[caffeine]] as the combination [[ergotamine/caffeine]].<ref name="Cafergot FDA label">{{cite web|url=http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=b4a06de6-f837-43a8-ae7a-aadb38dd2a7d|title= Cafergot- ergotamine tartrate and caffeine tablet, film coated| work = DailyMed | publisher = U.S. National Library of Medicine|url-status=live|archive-url= https://web.archive.org/web/20140116115705/http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=b4a06de6-f837-43a8-ae7a-aadb38dd2a7d#DA |archive-date=16 January 2014}}</ref><ref name="Migergot FDA label">{{cite web | title=Migergot- ergotamine tartrate and caffeine suppository | website=DailyMed | date=29 November 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3a31ad0c-7bdd-544b-f5df-a99d04cf541c | access-date=18 May 2024}}</ref>

The drug is a [[binding selectivity|non-selective]] [[receptor modulator|modulator]] or [[agonist]] of [[serotonin receptor]]s and other [[receptor (biochemistry)|receptor]]s.<ref name="pmid23815106" /><ref name="PDSPKiDatabase" /><ref name="KehlerLindskov2025" /> It is [[peripherally selective drug|peripherally selective]] and crosses into the [[brain]] in minimal amounts.<ref name="KehlerLindskov2025">{{cite journal | vauthors = Kehler J, Lindskov MS | title = Are the LSD-analogs lisuride and ergotamine examples of non-hallucinogenic serotonin 5-HT2A receptor agonists? | journal = Journal of Psychopharmacology | pages = 2698811251330741 | date = May 2025 | pmid = 40322975 | doi = 10.1177/02698811251330741 }}</ref>

[[Medicine|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|ergot fungus]] by [[Arthur Stoll]], at [[Sandoz]] in 1918, and was marketed as Gynergen in 1921.<ref>A. J. Giannini, A. E. Slaby. ''Drugs of Abuse''. Oradell, New Jersey: Medical Economics Books, 1989.</ref>