# Metergoline
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Metergoline
> Markdown URL: https://mediated.wiki/source/Metergoline.md
> Source: https://en.wikipedia.org/wiki/Metergoline
> Source revision: 1338034954
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462249407
| image = Metergoline.svg
| image_class = skin-invert-image
| width = 175px
| tradename = Contralac, Liserdol
| Drugs.com =
| MedlinePlus =
| pregnancy_category=
| legal_status = Rx-only
| routes_of_administration = [Oral](/source/Oral_administration)
| class =
| ATC_prefix = G02
| ATC_suffix = CB05
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 17692-51-2
| PubChem = 28693
| IUPHAR_ligand = 133
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26687
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1501393LY5
| ChEBI = 64216
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 19215
| synonyms = Methergoline; FI-6337; [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
| IUPAC_name = benzyl ''N''-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate
| C=25 | H=29 | N=3 | O=2
| SMILES = O=C(OCc1ccccc1)NC[C@@H]3C[C@@H]4c5cccc2c5c(cn2C)C[C@H]4N(C3)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WZHJKEUHNJHDLS-QTGUNEKASA-N
}}
'''Metergoline''' ({{Abbrlink|INN|International Nonproprietary Name|INN}}, {{Abbrlink|BAN|British Approved Name}}), also known as '''methergoline''' and sold under the brand names '''Contralac''' (veterinary) and '''Liserdol''' (clinical), is a [monoaminergic](/source/monoaminergic) medication of the [ergoline](/source/ergoline) group which is used as a [prolactin inhibitor](/source/prolactin_inhibitor) in the treatment of [hyperprolactinemia](/source/hyperprolactinemia) (high [prolactin](/source/prolactin) levels) and to suppress [lactation](/source/lactation).[{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA661|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=661–}}][{{cite book| vauthors = Plumb DC | chapter = Metergoline |title=Plumb's Veterinary Drug Handbook: Pocket| chapter-url = https://books.google.com/books?id=wshQDwAAQBAJ&pg=PA1057 |date=21 February 2018|publisher=John Wiley & Sons|isbn=978-1-119-34649-4|pages=1057–}}][{{cite book| vauthors = Johson CA | chapter = False Pregnancy, Disorders of Pregnancy and Parturition, and Mismating | veditors = Nelson RW, Couto CG |title=Small Animal Internal Medicine - E-Book| chapter-url=https://books.google.com/books?id=s-TXrwyo-_YC&pg=PA927|date=2 December 2008|publisher=Elsevier Health Sciences|isbn=978-0-323-06512-2|pages=927–}}]
==Pharmacology==
===Pharmacodynamics===
Metergoline is a [ligand](/source/ligand_(biochemistry)) of various [serotonin](/source/serotonin_receptor) and [dopamine receptor](/source/dopamine_receptor)s.[{{cite journal | vauthors = Hamon M, Mallat M, Herbet A, Nelson DL, Audinot M, Pichat L, Glowinski J | title = [3H]Metergoline: a new ligand of serotonin receptors in the rat brain | journal = Journal of Neurochemistry | volume = 36 | issue = 2 | pages = 613–626 | date = February 1981 | pmid = 7463079 | doi = 10.1111/j.1471-4159.1981.tb01634.x | s2cid = 20259621 }}][{{cite journal | vauthors = Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M | title = Agonist activity of sumatriptan and metergoline at the human 5-HT1D beta receptor: further evidence for a role of the 5-HT1D receptor in the action of sumatriptan | journal = European Journal of Pharmacology | volume = 227 | issue = 1 | pages = 99–102 | date = September 1992 | pmid = 1330643 | doi = 10.1016/0922-4106(92)90149-P }}][{{cite journal | vauthors = Glennon RA | title = Central serotonin receptors as targets for drug research | journal = J Med Chem | volume = 30 | issue = 1 | pages = 1–12 | date = January 1987 | pmid = 3543362 | doi = 10.1021/jm00384a001 | url = | quote = Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites}}]
{| class="wikitable"
|+ {{Nowrap|Activities of metergoline at various sites[{{cite web |url=https://pdsp.unc.edu/databases/pdsp.php?testFreeRadio=testFreeRadio&testLigand=Metergoline&doQuery=Submit+Query |title=PDSP Database - UNC |website=pdsp.unc.edu |access-date=15 January 2022 |archive-url=https://web.archive.org/web/20210416001542/https://pdsp.unc.edu/databases/pdsp.php?testFreeRadio=testFreeRadio&testLigand=Metergoline&doQuery=Submit+Query |archive-date=16 April 2021 |url-status=dead}}][{{cite journal | vauthors = Hoyer D, Clarke DE, Fozard JR, Hartig PR, Martin GR, Mylecharane EJ, Saxena PR, Humphrey PP | display-authors = 6 | title = International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin) | journal = Pharmacological Reviews | volume = 46 | issue = 2 | pages = 157–203 | date = June 1994 | pmid = 7938165 | doi = }}][{{cite book |vauthors=Pertz H, Eich E|title=Ergot|chapter=Ergot Alkaloids and their Derivatives as Ligands for Serotoninergic, Dopaminergic, and Adrenergic Receptors|year=1999|pages=432–462|doi=10.1201/9780203304198-21|isbn=9780429219764|chapter-url=http://chemistry.mdma.ch/hiveboard/palladium/pdf/Ergot%20-%20The%20Genus%20Claviceps%20%281999%29/TF3168ch14.pdf|archive-url=https://web.archive.org/web/20210416003930/http://chemistry.mdma.ch/hiveboard/palladium/pdf/Ergot%20-%20The%20Genus%20Claviceps%20%281999%29/TF3168ch14.pdf|archive-date=2021-04-16}}][{{cite journal | vauthors = Pauwels PJ | title = 5-HT 1B/D receptor antagonists | journal = General Pharmacology | volume = 29 | issue = 3 | pages = 293–303 | date = September 1997 | pmid = 9378233 | doi = 10.1016/s0306-3623(96)00460-0 }}][{{cite journal | vauthors = Hutcheson JD, Setola V, Roth BL, Merryman WD | title = Serotonin receptors and heart valve disease--it was meant 2B | journal = Pharmacology & Therapeutics | volume = 132 | issue = 2 | pages = 146–157 | date = November 2011 | pmid = 21440001 | pmc = 3179857 | doi = 10.1016/j.pharmthera.2011.03.008 | author3-link = Bryan Roth }}][{{cite journal | vauthors = Webster J | title = Dopamine agonist therapy in hyperprolactinemia | journal = The Journal of Reproductive Medicine | volume = 44 | issue = 12 Suppl | pages = 1105–1110 | date = December 1999 | pmid = 10649819 | doi = }}]}}
! Site
! Affinity (Ki [nM])
! Efficacy (Emax [%])
! Action
|-
| [5-HT1A](/source/5-HT1A_receptor)
| 4.3
| ?
| Antagonist
|-
| [5-HT1B](/source/5-HT1B_receptor)
| 5.2–36
| ?
| Partial agonist
|-
| [5-HT1D](/source/5-HT1D_receptor)
| 0.60–11.7
| ?
| Partial agonist
|-
| [5-HT1E](/source/5-HT1E_receptor)
| 776–1,122
| ?
| ?
|-
| [5-HT1F](/source/5-HT1F_receptor)
| 339–341
| ?
| ?
|-
| [5-HT2A](/source/5-HT2A_receptor)
| 0.12–2.3
| ?
| Antagonist
|-
| [5-HT2B](/source/5-HT2B_receptor)
| 0.71–1.8
| ?
| Antagonist
|-
| [5-HT2C](/source/5-HT2C_receptor)
| 0.18–1.8
| ?
| Antagonist
|-
| [5-HT3](/source/5-HT3_receptor)
| >5,000–7,400
| ?
| ?
|-
| [5-HT4](/source/5-HT4_receptor)
| 354
| ?
| ?
|-
| [5-HT5A](/source/5-HT5A_receptor)
| 630
| ?
| ?
|-
| [5-HT5B](/source/5-HT5B_receptor)
| 1,000
| ?
| ?
|-
| [5-HT6](/source/5-HT6_receptor)
| 61–400
| ?
| ?
|-
| [5-HT7](/source/5-HT7_receptor)
| 6.4–6.5
| ?
| Antagonist
|-
| [D2](/source/D2_receptor)
| ?
| ?
| Agonist
|- class="sortbottom"
| colspan="4" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' All sites are human except 5-HT3 (rat/pig), 5-HT4 (pig), and 5-HT5B (rat—no human counterpart).