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

Identification

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Name
Eslicarbazepine
Accession Number
DB14575
Type
Small Molecule
Groups
Approved
Description

Adjunctive Therapy for Adults with Partial-Onset Seizures

Structure
Thumb
Synonyms
  • Eslicarbazepina
  • S(+)-Liscarbazepine
External IDs
BIA 2-194 / BIA-2-194 / CGP-13751
Categories
UNII
S5VXA428R4
CAS number
104746-04-5
Weight
Average: 254.2839
Monoisotopic: 254.105527702
Chemical Formula
C15H14N2O2
InChI Key
BMPDWHIDQYTSHX-AWEZNQCLSA-N
InChI
InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)/t14-/m0/s1
IUPAC Name
(9S)-9-hydroxy-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaene-2-carboxamide
SMILES
NC(=O)N1C2=C(C[C@H](O)C3=C1C=CC=C3)C=CC=C2

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

The precise mechanism(s) by which eslicarbazepine exerts anticonvulsant activity is unknown but is thought to involve inhibition of voltage-gated sodium channels.

TargetActionsOrganism
AP2X purinoceptor 4Not AvailableHumans
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.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Eslicarbazepine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Eslicarbazepine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Eslicarbazepine.
3-isobutyl-1-methyl-7H-xanthineEslicarbazepine may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Eslicarbazepine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Eslicarbazepine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Eslicarbazepine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Eslicarbazepine.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Eslicarbazepine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when 5-methoxy-N,N-dimethyltryptamine is combined with Eslicarbazepine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. APTIOM ® (eslicarbazepine acetate [Link]
External Links
Human Metabolome Database
HMDB0060702
ChemSpider
8057180
ChEMBL
CHEMBL315985
Wikipedia
Eslicarbazepine_acetate

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 Solubility0.554 mg/mLALOGPS
logP1.26ALOGPS
logP1.73ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.1ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.56 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.29 m3·mol-1ChemAxon
Polarizability26.45 Å3ChemAxon
Number of Rings3ChemAxon
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Dibenzazepines
Direct Parent
Dibenzazepines
Alternative Parents
Azepines / Benzenoids / Ureas / Secondary alcohols / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Dibenzazepine / Azepine / Benzenoid / Carbonic acid derivative / Secondary alcohol / Urea / Azacycle / Organopnictogen compound / Organic nitrogen compound / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Zinc ion binding
Specific Function
Receptor for ATP that acts as a ligand-gated ion channel. This receptor is insensitive to the antagonists PPADS and suramin.
Gene Name
P2RX4
Uniprot ID
Q99571
Uniprot Name
P2X purinoceptor 4
Molecular Weight
43368.725 Da
References
  1. Tian M, Abdelrahman A, Weinhausen S, Hinz S, Weyer S, Dosa S, El-Tayeb A, Muller CE: Carbamazepine derivatives with P2X4 receptor-blocking activity. Bioorg Med Chem. 2014 Feb 1;22(3):1077-88. doi: 10.1016/j.bmc.2013.12.035. Epub 2013 Dec 25. [PubMed:24411477]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
The FDA label reports a mild activation of UGT1A1- mediated glucuronidation was observed in human hepatic microsomes, in relation to eslicarbazepine metabolism.
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. APTIOM ® (eslicarbazepine acetate [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Bialer M, Soares-da-Silva P: Pharmacokinetics and drug interactions of eslicarbazepine acetate. Epilepsia. 2012 Jun;53(6):935-46. doi: 10.1111/j.1528-1167.2012.03519.x. Epub 2012 May 21. [PubMed:22612290]
  2. Bialer M, White HS: Key factors in the discovery and development of new antiepileptic drugs. Nat Rev Drug Discov. 2010 Jan;9(1):68-82. doi: 10.1038/nrd2997. [PubMed:20043029]
  3. Galiana GL, Gauthier AC, Mattson RH: Eslicarbazepine Acetate: A New Improvement on a Classic Drug Family for the Treatment of Partial-Onset Seizures. Drugs R D. 2017 Sep;17(3):329-339. doi: 10.1007/s40268-017-0197-5. [PubMed:28741150]
  4. Eslicarbazepine, PDR [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. APTIOM ® (eslicarbazepine acetate [Link]

Drug created on July 20, 2018 15:43 / Updated on September 24, 2019 12:39