Metergoline

{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462249407 | image = Metergoline.svg | image_class = skin-invert-image | width = 175px

<!-- Clinical data --> | tradename = Contralac, Liserdol | Drugs.com = | MedlinePlus = | pregnancy_category= | legal_status = Rx-only | routes_of_administration = Oral | class = | ATC_prefix = G02 | ATC_suffix = CB05

<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

<!-- Identifiers --> | 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

<!-- Chemical data --> | IUPAC_name = benzyl ''N''-<nowiki>[[</nowiki>(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 medication of the ergoline group which is used as a prolactin inhibitor in the treatment of hyperprolactinemia (high prolactin levels) and to suppress lactation.<ref name="IndexNominum2000">{{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–}}</ref><ref name="Plumb2018">{{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–}}</ref><ref name="NelsonCouto2008">{{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–}}</ref>

==Pharmacology==

===Pharmacodynamics=== Metergoline is a ligand of various serotonin and dopamine receptors.<ref name="PDSPKiDatabase" /><ref name="pmid7938165" /><ref name="pmid7463079">{{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 }}</ref><ref name="pmid1330643">{{cite journal | vauthors = Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M | title = Agonist activity of sumatriptan and metergoline at the human 5-HT_1D beta receptor: further evidence for a role of the 5-HT_1D 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 }}</ref><ref name="pmid10649819" /><ref name="Glennon1987">{{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}}</ref>

{| class="wikitable" |+ {{Nowrap|Activities of metergoline at various sites<ref name="PDSPKiDatabase">{{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}}</ref><ref name="pmid7938165">{{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 = }}</ref><ref name="PertzHeich1999">{{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}}</ref><ref name="pmid9378233">{{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 }}</ref><ref name="pmid21440001">{{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 }}</ref><ref name="pmid10649819">{{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 = }}</ref>}} ! Site ! Affinity (K_i [nM]) ! Efficacy (E_max [%]) ! Action |- | 5-HT_1A | 4.3 | ? | Antagonist |- | 5-HT_1B | 5.2–36 | ? | Partial agonist |- | 5-HT_1D | 0.60–11.7 | ? | Partial agonist |- | 5-HT_1E | 776–1,122 | ? | ? |- | 5-HT_1F | 339–341 | ? | ? |- | 5-HT_2A | 0.12–2.3 | ? | Antagonist |- | 5-HT_2B | 0.71–1.8 | ? | Antagonist |- | 5-HT_2C | 0.18–1.8 | ? | Antagonist |- | 5-HT₃ | >5,000–7,400 | ? | ? |- | 5-HT₄ | 354 | ? | ? |- | 5-HT_5A | 630 | ? | ? |- | 5-HT_5B | 1,000 | ? | ? |- | 5-HT₆ | 61–400 | ? | ? |- | 5-HT₇ | 6.4–6.5 | ? | Antagonist |- | D₂ | ? | ? | 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-HT_5B (rat—no human counterpart).<ref name="PDSPKiDatabase" /> |}

== References == {{Reflist}}

== External links == * {{MeshName|Metergoline}}

{{Prolactin inhibitors and anti-inflammatory products for vaginal administration}} {{Other gynecologicals}} {{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 = {{Dopamine receptor modulators}} {{Prolactin receptor modulators}} {{Serotonin receptor modulators}} }} {{Ergolines}}

Category:Antipsychotics Category:Carbamates Category:Dopamine agonists Category:Ergolines Category:Hallucinogen antidotes Category:Prolactin inhibitors Category:Serotonin receptor antagonists