Metergoline

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Metergoline is an ergot-derivative that acts as an antagonist at certain 5-HT receptor subtypes and as an agonist at dopamine receptors. It is often used in situations where inhibition of prolactin is desirable.

Generic Name
Metergoline
DrugBank Accession Number
DB13520
Background

Metergoline is an ergot-derived psychoactive drug that acts as a ligand for serotonin and dopamine receptors. Metergoline is an antagonist at various 5-HT receptor subtypes at a relatively low concentration and agonist at dopamine receptors.3 Its use has been studied in various clinical settings such as a treatment for seasonal affective disorder, prolactin hormone regulation due to its inhibitory effect on prolactin release,1 premenstrual dysphoric disorder in women and antianxiety treatment.2

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 403.526
Monoisotopic: 403.225977186
Chemical Formula
C25H29N3O2
Synonyms
  • Metergolina
  • Metergoline
  • Metergolinum
External IDs
  • FI 6337
  • FI-6337
  • FI6337

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USodium channel protein type 2 subunit alpha
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Metergoline.
AcebutololAcebutolol may increase the vasoconstricting activities of Metergoline.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Metergoline.
AcemetacinThe risk or severity of hypertension can be increased when Metergoline is combined with Acemetacin.
AcenocoumarolThe risk or severity of adverse effects can be increased when Metergoline is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Metergoline.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Metergoline.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Metergoline.
AclidiniumMetergoline may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Metergoline.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Liserdol

Categories

ATC Codes
G02CB05 — Metergoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Indoloquinolines
Direct Parent
Indoloquinolines
Alternative Parents
Ergoline and derivatives / Benzoquinolines / Pyrroloquinolines / 3-alkylindoles / Benzyloxycarbonyls / N-alkylindoles / Isoindoles and derivatives / Aralkylamines / Piperidines / N-methylpyrroles
show 9 more
Substituents
3-alkylindole / Alkaloid or derivatives / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoquinoline / Benzyloxycarbonyl / Carbamic acid ester
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carbamate ester, ergoline alkaloid (CHEBI:64216)
Affected organisms
Not Available

Chemical Identifiers

UNII
1501393LY5
CAS number
17692-51-2
InChI Key
WZHJKEUHNJHDLS-QTGUNEKASA-N
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
IUPAC Name
benzyl N-{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}carbamate
SMILES
[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@@]1([H])C[C@@H](CNC(=O)OCC1=CC=CC=C1)CN2C

References

General References
  1. Delitala G: Stimulating action of sulpiride and pimozide on prolactin release. Effect on bromocriptine, L-dopa and metergoline administration. Acta Endocrinol (Copenh). 1977 Oct;86(2):251-6. [Article]
  2. Graeff FG, Zuardi AW, Giglio JS, Lima Filho EC, Karniol IG: Effect of metergoline on human anxiety. Psychopharmacology (Berl). 1985;86(3):334-8. [Article]
  3. Lee JH, Liu J, Shin M, Hong M, Nah SY, Bae H: Metergoline inhibits the neuronal Nav1.2 voltage-dependent Na(+) channels expressed in Xenopus oocytes. Acta Pharmacol Sin. 2014 Jul;35(7):862-8. doi: 10.1038/aps.2014.30. Epub 2014 Jun 9. [Article]
KEGG Drug
D07218
PubChem Compound
28693
PubChem Substance
347829303
ChemSpider
26687
BindingDB
30704
RxNav
6834
ChEBI
64216
ChEMBL
CHEMBL19215
ZINC
ZINC000003812975
Wikipedia
Metergoline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet
Tablet, film coated
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP3.99ChemAxon
pKa (Strongest Acidic)15.69ChemAxon
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.5 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.3 m3·mol-1ChemAxon
Polarizability46.81 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ir0-4794200000-d04091d908ab86f9807e

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
Gene Name
SCN2A
Uniprot ID
Q99250
Uniprot Name
Sodium channel protein type 2 subunit alpha
Molecular Weight
227972.64 Da
References
  1. Lee JH, Liu J, Shin M, Hong M, Nah SY, Bae H: Metergoline inhibits the neuronal Nav1.2 voltage-dependent Na(+) channels expressed in Xenopus oocytes. Acta Pharmacol Sin. 2014 Jul;35(7):862-8. doi: 10.1038/aps.2014.30. Epub 2014 Jun 9. [Article]

Drug created on June 23, 2017 20:43 / Updated on May 19, 2021 03:45