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Metergoline

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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
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC25H29N3O2
Molar mass403.526 g·mol−1
3D model (JSmol)
  • O=C(OCc1ccccc1)NC[C@@H]3C[C@@H]4c5cccc2c5c(cn2C)C[C@H]4N(C3)C
  • 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 (INNTooltip INN, BANTooltip 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.[1][2][3]

Pharmacology

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Pharmacodynamics

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Metergoline is a ligand of various serotonin and dopamine receptors.[4][5][6][7][8][9]

Activities of metergoline at various sites[4][5][10][11][12][8]
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).[4]

References

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  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 661–. ISBN 978-3-88763-075-1.
  2. ^ Plumb DC (21 February 2018). "Metergoline". Plumb's Veterinary Drug Handbook: Pocket. John Wiley & Sons. pp. 1057–. ISBN 978-1-119-34649-4.
  3. ^ Johson CA (2 December 2008). "False Pregnancy, Disorders of Pregnancy and Parturition, and Mismating". In Nelson RW, Couto CG (eds.). Small Animal Internal Medicine - E-Book. Elsevier Health Sciences. pp. 927–. ISBN 978-0-323-06512-2.
  4. ^ a b c "PDSP Database - UNC". pdsp.unc.edu. Archived from the original on 16 April 2021. Retrieved 15 January 2022.
  5. ^ a b Hoyer D, Clarke DE, Fozard JR, Hartig PR, Martin GR, Mylecharane EJ, et al. (June 1994). "International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin)". Pharmacological Reviews. 46 (2): 157–203. PMID 7938165.
  6. ^ Hamon M, Mallat M, Herbet A, Nelson DL, Audinot M, Pichat L, Glowinski J (February 1981). "[3H]Metergoline: a new ligand of serotonin receptors in the rat brain". Journal of Neurochemistry. 36 (2): 613–626. doi:10.1111/j.1471-4159.1981.tb01634.x. PMID 7463079. S2CID 20259621.
  7. ^ Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M (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. 227 (1): 99–102. doi:10.1016/0922-4106(92)90149-P. PMID 1330643.
  8. ^ a b Webster J (December 1999). "Dopamine agonist therapy in hyperprolactinemia". The Journal of Reproductive Medicine. 44 (12 Suppl): 1105–1110. PMID 10649819.
  9. ^ Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
  10. ^ 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.
  11. ^ Pauwels PJ (September 1997). "5-HT 1B/D receptor antagonists". General Pharmacology. 29 (3): 293–303. doi:10.1016/s0306-3623(96)00460-0. PMID 9378233.
  12. ^ Hutcheson JD, Setola V, Roth BL, Merryman WD (November 2011). "Serotonin receptors and heart valve disease--it was meant 2B". Pharmacology & Therapeutics. 132 (2): 146–157. doi:10.1016/j.pharmthera.2011.03.008. PMC 3179857. PMID 21440001.
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