Metergoline

{{Short description|Chemical compound}}

{{Drugbox

| 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

| 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 = {{cascite|changed|??}}

| CAS_number = 17692-51-2

| ATC_prefix = G02

| ATC_suffix = CB05

| 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

| 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.{{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 of various serotonin and dopamine receptors.{{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 }}

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

| 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

class="sortbottom"

| colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;" | Notes: All sites are human except 5-HT3 (rat/pig), 5-HT4 (pig), and 5-HT5B (rat—no human counterpart).

References

{{Reflist}}