Metergoline

Last updated
Metergoline
Metergoline.svg
Clinical data
Trade names Contralac, 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 InfoCard 100.037.881 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H29N3O2
Molar mass 403.526 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 Yes check.svgY
  • Key:WZHJKEUHNJHDLS-QTGUNEKASA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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]
SiteAffinity (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]

Related Research Articles

Ergotamine Chemical compound in the ergot family of alkaloids

Ergotamine, sold under the brand names Cafergot and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor.

Bromocriptine Organic Chemical Compound

Bromocriptine, originally marketed as Parlodel and subsequently under many brand names, is an ergoline derivative and dopamine agonist that is used in the treatment of pituitary tumors, Parkinson's disease, hyperprolactinaemia, neuroleptic malignant syndrome, and, as an adjunct, type 2 diabetes.

Pergolide

Pergolide, sold under the brand name Permax and Prascend (veterinary) among others, is an ergoline-based dopamine receptor agonist used in some countries for the treatment of Parkinson's disease. Parkinson's disease is associated with reduced dopamine activity in the substantia nigra of the brain. Pergolide acts on many of the same receptors as dopamine to increase receptor activity.

5-HT receptor Class of transmembrane proteins

5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission. The serotonin receptors are activated by the neurotransmitter serotonin, which acts as their natural ligand.

Triptan Class of pharmaceutical drugs

Triptans are a family of tryptamine-based drugs used as abortive medication in the treatment of migraines and cluster headaches. This drug class was first introduced in the 1990s. While effective at treating individual headaches, they do not provide preventive treatment and are not considered a cure. They are not effective for the treatment of tension–type headache, except in persons who also experience migraines. Triptans do not relieve other kinds of pain.

Amoxapine Chemical compound

Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCAs). It is the N-demethylated metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1992.

Cabergoline Chemical compound

Cabergoline, sold under the brand name Dostinex among others, is a dopaminergic medication used in the treatment of high prolactin levels, prolactinomas, Parkinson's disease, and for other indications. It is taken by mouth.

Pindolol Chemical compound

Pindolol, sold under the brand name Visken among others, is a nonselective beta blocker which is used in the treatment of hypertension. It is also an antagonist of the serotonin 5-HT1A receptor, preferentially blocking inhibitory 5-HT1A autoreceptors, and has been researched as an add-on therapy to selective serotonin reuptake inhibitors (SSRIs) in the treatment of depression.

Dihydroergotamine An ergot alkaloid used to treat migraines

Dihydroergotamine (DHE), sold under the brand names D.H.E. 45 and Migranal among others, is an ergot alkaloid used to treat migraines. It is a derivative of ergotamine. It is administered as a nasal spray or injection and has an efficacy similar to that of sumatriptan. Nausea is a common side effect.

Methylergometrine Chemical compound

Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.

Methysergide Chemical compound

Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to adverse effects. It is taken by mouth.

Lisuride Chemical compound

Lisuride, sold under the brand name Dopergin among others, is a monoaminergic medication of the ergoline class which is used in the treatment of Parkinson's disease, migraine, and high prolactin levels. It is taken by mouth.

Serotonin receptor agonist

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

Mesulergine

Mesulergine (INN) (developmental code name CU-32085) is a drug of the ergoline group which was never marketed. It acts on serotonin and dopamine receptors. Specifically, it is an agonist of dopamine D2-like receptors and serotonin 5-HT6 receptors and an antagonist of serotonin 5-HT2A, 5-HT2B, 5-HT2C, and 5-HT7 receptors. It also has affinity for the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1F, and 5-HT5A receptors. The compound had entered clinical trials for the treatment of Parkinson's disease; however, further development was halted due to adverse histological abnormalities in rats. It was also investigated for the treatment of hyperprolactinemia (high prolactin levels).

Terguride Chemical compound

Terguride, sold under the brand name Teluron, is a serotonin receptor antagonist and dopamine receptor agonist of the ergoline family. It is approved for and used as a prolactin inhibitor in the treatment of hyperprolactinemia in Japan. Terguride is taken by mouth.

CP-94253 Potent and selective serotonin 5-HT1B receptor agonist

CP-94253 is a drug which acts as a potent and selective serotonin 5-HT1B receptor agonist, with approximately 25x and 40x selectivity over the closely related 5-HT1D and 5-HT1A receptors. It has a range of behavioral effects, based on animal testing. The effects include the following: promoting wakefulness by increasing dopamine release in the brain; reducing food intake and promoting satiety; enhancing the reinforcing effects of cocaine; and possible antidepressant effects.

S-15535

S-15535 is a phenylpiperazine drug which is a potent and highly selective 5-HT1A receptor ligand that acts as an agonist and antagonist at the presynaptic and postsynaptic 5-HT1A receptors, respectively. It has anxiolytic properties.

Prolactin modulator

A prolactin modulator is a drug which affects the hypothalamic–pituitary–prolactin axis by modulating the secretion of the pituitary hormone prolactin from the anterior pituitary gland. Prolactin inhibitors suppress and prolactin releasers induce the secretion of prolactin, respectively.

Amesergide Chemical compound

Amesergide is a serotonin receptor antagonist of the ergoline and lysergamide families related to methysergide which was under development by Eli Lilly and Company for the treatment of a variety of conditions including depression, anxiety, schizophrenia, male sexual dysfunction, migraine, and thrombosis but was never marketed. It reached phase II clinical trials for the treatment of depression, erectile dysfunction, and premature ejaculation prior to the discontinuation of its development.

Bromerguride

Bromerguride (INN), also known as 2-bromolisuride, is an antidopaminergic and serotonergic agent of the ergoline group which was described as having atypical antipsychotic properties but was never marketed. It was the first antidopaminergic ergoline derivative to be discovered. The pharmacodynamic actions of bromerguride are said to be "reversed" relative to its parent compound lisuride, a dopaminergic agent.

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.
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