Metergoline

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
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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 checkY
  • Key:WZHJKEUHNJHDLS-QTGUNEKASA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

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. 1 2 3 "Archived copy". pdsp.unc.edu. Archived from the original on 16 April 2021. Retrieved 15 January 2022.{{cite web}}: CS1 maint: archived copy as title (link)
  5. 1 2 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. 1 2 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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