Metergoline
Chemical compound
title: "Metergoline" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antipsychotics", "carbamates", "dopamine-agonists", "ergolines", "hallucinogen-antidotes", "prolactin-inhibitors", "serotonin-receptor-antagonists"] description: "Chemical compound" topic_path: "general/antipsychotics" source: "https://en.wikipedia.org/wiki/Metergoline" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462249407 | 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 | image = Metergoline.svg | image_class = skin-invert-image | width = 225px
| tradename = Contralac, Liserdol | Drugs.com = | MedlinePlus = | pregnancy_category= | legal_status = Rx-only | routes_of_administration = Oral
| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
| CAS_number_Ref = | CAS_number = 17692-51-2 | ATC_prefix = G02 | ATC_suffix = CB05 | PubChem = 28693 | IUPHAR_ligand = 133 | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 26687 | UNII_Ref = | UNII = 1501393LY5 | ChEBI = 64216 | ChEMBL_Ref = | ChEMBL = 19215 | synonyms = Methergoline; FI-6337; [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
| 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 = | 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 = | StdInChIKey = WZHJKEUHNJHDLS-QTGUNEKASA-N
Metergoline (, ), also known as methergoline and sold under the brand names Contralac (veterinary) and Liserdol (clinical), is a monoaminergic medication of the ergoline group which is used as a prolactin inhibitor in the treatment of hyperprolactinemia (high prolactin levels) and to suppress lactation.
Pharmacology
Pharmacodynamics
Metergoline is a ligand of various serotonin and dopamine receptors.
::data[format=table title="{{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 | 4.3 | ? | Antagonist |
| 5-HT1B | 5.2–36 | ? | Partial agonist |
| 5-HT1D | 0.60–11.7 | ? | Partial agonist |
| 5-HT1E | 776–1,122 | ? | ? |
| 5-HT1F | 339–341 | ? | ? |
| 5-HT2A | 0.12–2.3 | ? | Antagonist |
| 5-HT2B | 0.71–1.8 | ? | Antagonist |
| 5-HT2C | 0.18–1.8 | ? | Antagonist |
| 5-HT3 | 5,000–7,400 | ? | ? |
| 5-HT4 | 354 | ? | ? |
| 5-HT5A | 630 | ? | ? |
| 5-HT5B | 1,000 | ? | ? |
| 5-HT6 | 61–400 | ? | ? |
| 5-HT7 | 6.4–6.5 | ? | Antagonist |
| D2 | ? | ? | Agonist |
| Notes: All sites are human except 5-HT3 (rat/pig), 5-HT4 (pig), and 5-HT5B (rat—no human counterpart). | |||
| :: |
References
References
- (2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
- (21 February 2018). "Plumb's Veterinary Drug Handbook: Pocket". John Wiley & Sons.
- (2 December 2008). "Small Animal Internal Medicine - E-Book". Elsevier Health Sciences.
- (February 1981). "[3H]Metergoline: a new ligand of serotonin receptors in the rat brain". Journal of Neurochemistry.
- (September 1992). "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". European Journal of Pharmacology.
- (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem.
- "PDSP Database - UNC".
- (June 1994). "International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin)". Pharmacological Reviews.
- (1999). "Ergot".
- (September 1997). "5-HT 1B/D receptor antagonists". General Pharmacology.
- (November 2011). "Serotonin receptors and heart valve disease--it was meant 2B". Pharmacology & Therapeutics.
- (December 1999). "Dopamine agonist therapy in hyperprolactinemia". The Journal of Reproductive Medicine.
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