Metergoline

Metergoline
Clinical data
Trade names	Contralac, Liserdol
Other names	Methergoline; FI-6337; [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
Routes of; administration	Oral
ATC code	G02CB05 (WHO) ;
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	17692-51-2 ;
PubChem CID	28693;
IUPHAR/BPS	133;
ChemSpider	26687 ;
UNII	1501393LY5;
ChEBI	CHEBI:64216;
ChEMBL	ChEMBL19215 ;
CompTox Dashboard (EPA)	DTXSID5042584 ;
ECHA InfoCard	100.037.881
Chemical and physical data
Formula	C25H29N3O2
Molar mass	403.526 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:WZHJKEUHNJHDLS-QTGUNEKASA-N ;
	(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

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 (K_i [nM])	Efficacy (E_max [%])	Action
5-HT_1A	4.3	?	Agonist
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
Notes: All sites are human except 5-HT₃ (rat/pig), 5-HT₄ (pig), and 5-HT_5B (rat—no human counterpart).^[4]

References

^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 661–. ISBN 978-3-88763-075-1.
^ Donald C. Plumb (21 February 2018). Plumb's Veterinary Drug Handbook: Pocket. John Wiley & Sons. pp. 1057–. ISBN 978-1-119-34649-4.
^ 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.
^ ^a ^b ^c "PDSP Database - UNC". pdsp.unc.edu. Archived from the original on 16 April 2021. Retrieved 15 January 2022.
^ ^a ^b 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.
^ 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.
^ Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M (1992). "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". Eur. J. Pharmacol. 227 (1): 99–102. doi:10.1016/0922-4106(92)90149-P. PMID 1330643.
^ ^a ^b Webster J (December 1999). "Dopamine agonist therapy in hyperprolactinemia". J Reprod Med. 44 (12 Suppl): 1105–10. PMID 10649819.
^ 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.
^ 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.
^ 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.

External links

Metergoline at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

[IndexNominum2000-1] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 661–. ISBN 978-3-88763-075-1.

[Plumb2018-2] Donald C. Plumb (21 February 2018). Plumb's Veterinary Drug Handbook: Pocket. John Wiley & Sons. pp. 1057–. ISBN 978-1-119-34649-4.

[NelsonCouto2008-3] 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.

[PDSPKiDatabase-4] "PDSP Database - UNC". pdsp.unc.edu. Archived from the original on 16 April 2021. Retrieved 15 January 2022.

[pmid7938165-5] 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.

[pmid7463079-6] 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.

[pmid1330643-7] Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M (1992). "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". Eur. J. Pharmacol. 227 (1): 99–102. doi:10.1016/0922-4106(92)90149-P. PMID 1330643.

[pmid10649819-8] Webster J (December 1999). "Dopamine agonist therapy in hyperprolactinemia". J Reprod Med. 44 (12 Suppl): 1105–10. PMID 10649819.

[PertzHeich1999-9] 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.

[pmid9378233-10] 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.

[pmid21440001-11] 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.

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v t e Prolactin inhibitors and anti-inflammatory products for vaginal administration (G02CB–G02CC)
Prolactin inhibitors	Bromocriptine Cabergoline Ergoloid Lisuride Metergoline Pergolide Quinagolide Terguride
Anti-inflammatory products for vaginal administration	Benzydamine Ibuprofen Flunoxaprofen Naproxen

v t e Tocolytics/labor repressants (G02CA)
β₂ adrenoreceptor agonists	Bedoradrine Buphenine Dextrofemine Fenoterol Hexoprenaline Isoxsuprine Racefemine Ritodrine Terbutaline
Oxytocin antagonists	Atosiban
NSAIDs	Indometacin
Calcium channel blockers	Nifedipine
Myosin inhibitors	Magnesium sulfate

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)