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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyMetergoline
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
- Approved
- 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.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
- Structure
Structure for Metergoline (DB13520)
- Synonyms
- Metergolina
- Metergoline
- Metergolinum
- External IDs
- FI 6337 / FI-6337 / FI6337
- International/Other Brands
- Liserdol
- Categories
- Agents that produce hypertension
- Alkaloids
- Antidepressive Agents
- Central Nervous System Depressants
- Dopamine Agents
- Dopamine Agonists
- Ergolines
- Ergot Alkaloids and Derivatives
- Ergot-derivative Dopamine Receptor Agonists
- Genito Urinary System and Sex Hormones
- Heterocyclic Compounds, Fused-Ring
- Neurotransmitter Agents
- Prolactine Inhibitors
- Serotonin Agents
- Serotonin Receptor Agonists
- 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@@]12CC3=CN(C)C4=CC=CC(=C34)[C@@]1([H])C[C@@H](CNC(=O)OCC1=CC=CC=C1)CN2C
Pharmacology
- Indication
- Not Available
- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism USodium channel protein type 2 subunit alpha inhibitorHumans - 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
- 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.
Drug Interaction Unlock Additional Data(R)-warfarin The risk or severity of adverse effects can be increased when Metergoline is combined with (R)-warfarin. (S)-Warfarin The risk or severity of adverse effects can be increased when Metergoline is combined with (S)-Warfarin. 1-benzylimidazole The risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Metergoline. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Metergoline. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Metergoline is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Metergoline. 4-Bromo-2,5-dimethoxyphenethylamine Metergoline may increase the hypertensive and vasoconstricting activities of 4-Bromo-2,5-dimethoxyphenethylamine. 4-hydroxycoumarin The risk or severity of adverse effects can be increased when Metergoline is combined with 4-hydroxycoumarin. 4-Methoxyamphetamine Metergoline may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine Metergoline may increase the vasoconstricting activities of 5-methoxy-N,N-dimethyltryptamine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- General References
- 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]
- 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]
- 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]
- External Links
- KEGG Drug
- D07218
- PubChem Compound
- 28693
- PubChem Substance
- 347829303
- ChemSpider
- 26687
- BindingDB
- 30704
- RxNav
- 6834
- ChEBI
- 64216
- ChEMBL
- CHEMBL19215
- ZINC
- ZINC000003812975
- Wikipedia
- Metergoline
- ATC Codes
- G02CB05 — Metergoline
Clinical Trials
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
Property Value Source Water Solubility 0.0109 mg/mL ALOGPS logP 3.99 ALOGPS logP 2.04 ChemAxon logS -4.6 ALOGPS pKa (Strongest Acidic) 4.35 ChemAxon pKa (Strongest Basic) 8.69 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 49.99 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 120.09 m3·mol-1 ChemAxon Polarizability 47.33 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0ir0-4794200000-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
- 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
- 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 March 01, 2020 21:34
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