Metergoline

Metergoline (INN, BAN), 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.[1][2][3]

Metergoline
Clinical data
Trade namesContralac, Liserdol
Other namesMethergoline; FI-6337; [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
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
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.037.881
Chemical and physical data
FormulaC25H29N3O2
Molar mass403.526 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCc1ccccc1)NC[C@@H]3C[C@@H]4c5cccc2c5c(cn2C)C[C@H]4N(C3)C
InChI
  • InChI=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 Y
  • Key:WZHJKEUHNJHDLS-QTGUNEKASA-N Y
 NY (what is this?)  (verify)

Pharmacology

Pharmacodynamics

Metergoline is a ligand of various serotonin and dopamine receptors.[4][5][6][7][8]

Activities of metergoline at various sites[4][5][9][10][11][8]
Site Affinity (Ki [nM]) Efficacy (Emax [%]) Action
5-HT1A 4.3  ? Agonist
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).[4]

References
  1. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 661–. ISBN 978-3-88763-075-1.
  2. Donald C. Plumb (21 February 2018). Plumb's Veterinary Drug Handbook: Pocket. John Wiley & Sons. pp. 1057–. ISBN 978-1-119-34649-4.
  3. Richard W. Nelson; C. Guillermo Couto (2 December 2008). Small Animal Internal Medicine - E-Book. Elsevier Health Sciences. pp. 927–. ISBN 978-0-323-06512-2.
  4. "PDSP Database - UNC". pdsp.unc.edu. Archived from the original on 16 April 2021. Retrieved 15 January 2022.
  5. Hoyer D, Clarke DE, Fozard JR, Hartig PR, Martin GR, Mylecharane EJ, Saxena PR, Humphrey PP (June 1994). "International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin)". Pharmacol Rev. 46 (2): 157–203. PMID 7938165.
  6. Hamon M, Mallat M, Herbet A, et al. (February 1981). "[3H]Metergoline: a new ligand of serotonin receptors in the rat brain". Journal of Neurochemistry. 36 (2): 613–26. doi:10.1111/j.1471-4159.1981.tb01634.x. PMID 7463079. S2CID 20259621.
  7. Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M (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". Eur. J. Pharmacol. 227 (1): 99–102. doi:10.1016/0922-4106(92)90149-P. PMID 1330643.
  8. Webster J (December 1999). "Dopamine agonist therapy in hyperprolactinemia". J Reprod Med. 44 (12 Suppl): 1105–10. PMID 10649819.
  9. Pertz H, Eich E (1999). "Ergot Alkaloids and their Derivatives as Ligands for Serotoninergic, Dopaminergic, and Adrenergic Receptors" (PDF). Ergot. pp. 432–462. doi:10.1201/9780203304198-21. ISBN 9780429219764. Archived from the original (PDF) on 2021-04-16.
  10. Pauwels PJ (September 1997). "5-HT 1B/D receptor antagonists". Gen Pharmacol. 29 (3): 293–303. doi:10.1016/s0306-3623(96)00460-0. PMID 9378233.
  11. Hutcheson JD, Setola V, Roth BL, Merryman WD (November 2011). "Serotonin receptors and heart valve disease--it was meant 2B". Pharmacol Ther. 132 (2): 146–57. doi:10.1016/j.pharmthera.2011.03.008. PMC 3179857. PMID 21440001.
  • Metergoline at the US National Library of Medicine Medical Subject Headings (MeSH)
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