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
Structure for Metergoline (DB13520)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Amenorrhea •••••••••••• ••••••• •••• •••••• Treatment of Chromaffin-tissue derived tumors •••••••••••• ••••••• •••• •••••• Treatment of Diarrhea •••••••••••• ••••••• •••• •••••• Treatment of Gastrointestinal hypermotility •••••••••••• ••••••• ••••••••• ••••••• •••• •••••• Treatment of Gastrointestinal hypermotility •••••••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with Metergoline. Acebutolol Acebutolol may increase the vasoconstricting activities of Metergoline. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Metergoline. Acemetacin The risk or severity of hypertension can be increased when Metergoline is combined with Acemetacin. Acenocoumarol The risk or severity of adverse effects can be increased when Metergoline is combined with Acenocoumarol. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Liserdol
Categories
- ATC Codes
- G02CB05 — Metergoline
- Drug 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
- Serotonin Receptor Antagonists
- 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
- 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]
- 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]
- 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]
- External Links
- KEGG Drug
- D07218
- PubChem Compound
- 28693
- PubChem Substance
- 347829303
- ChemSpider
- 26687
- BindingDB
- 30704
- 6834
- ChEBI
- 64216
- ChEMBL
- CHEMBL19215
- ZINC
- ZINC000003812975
- Wikipedia
- Metergoline
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Tablet, film coated - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP 3.99 Chemaxon pKa (Strongest Acidic) 15.69 Chemaxon pKa (Strongest Basic) 8.22 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.5 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 119.3 m3·mol-1 Chemaxon Polarizability 46.81 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 221.4227891 predictedDarkChem Lite v0.1.0 [M-H]- 189.24178 predictedDeepCCS 1.0 (2019) [M+H]+ 221.2373891 predictedDarkChem Lite v0.1.0 [M+H]+ 191.63736 predictedDeepCCS 1.0 (2019) [M+Na]+ 221.8328891 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.54988 predictedDeepCCS 1.0 (2019)
Targets
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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
- 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 at June 23, 2017 20:43 / Updated at May 19, 2021 03:45