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

Identification

Name
Metergoline
Accession Number
DB13520
Type
Small Molecule
Groups
Experimental
Description

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 [A27181]. 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].

Structure
Thumb
Synonyms
Not Available
External IDs
FI 6337 / FI-6337
Categories
UNII
1501393LY5
CAS number
17692-51-2
Weight
Average: 403.526
Monoisotopic: 403.225977186
Chemical Formula
C25H29N3O2
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
N-{[(2R,4R,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}(benzyloxy)carboximidic acid
SMILES
[H][C@]1(CN=C(O)OCC2=CC=CC=C2)CN(C)[C@]2([H])CC3=CN(C)C4=CC=CC(=C34)[C@@]2([H])C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USodium channel protein type 2 subunit alpha
inhibitor
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
4-MethoxyamphetamineMetergoline may increase the hypertensive activities of 4-Methoxyamphetamine.
AcebutololAcebutolol may increase the vasoconstricting activities of Metergoline.
AcetazolamideThe risk or severity of adverse effects can be increased when Metergoline is combined with Acetazolamide.
Acetyl sulfisoxazoleThe risk or severity of adverse effects can be increased when Metergoline is combined with Acetyl sulfisoxazole.
AgmatineMetergoline may increase the hypertensive and vasoconstricting activities of Agmatine.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Metergoline.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Metergoline.
AmbroxolThe risk or severity of adverse effects can be increased when Metergoline is combined with Ambroxol.
AmikacinThe risk or severity of adverse effects can be increased when Amikacin is combined with Metergoline.
AmiodaroneThe metabolism of Metergoline can be decreased when combined with Amiodarone.
Food Interactions
Not Available

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. [PubMed:578618]
  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. [PubMed:3929304]
External Links
PubChem Compound
28693
PubChem Substance
347829303
ChemSpider
26687
BindingDB
30704
ChEBI
64216
ChEMBL
CHEMBL19215
Wikipedia
Metergoline
ATC Codes
G02CB05 — Metergoline

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0109 mg/mLALOGPS
logP3.99ALOGPS
logP2.04ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.99 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.09 m3·mol-1ChemAxon
Polarizability47.33 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

Taxonomy

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
Ergoline skeleton / Indoloquinoline / Benzoquinoline / Pyrroloquinoline / Benzyloxycarbonyl / N-alkylindole / 3-alkylindole / Indole / Indole or derivatives / Isoindole or derivatives
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carbamate ester, ergoline alkaloid (CHEBI:64216)

Targets

Kind
Protein
Organism
Human
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. [PubMed:24909513]

Drug created on June 23, 2017 14:43 / Updated on August 02, 2018 06:53