This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Summary
Eslicarbazepine is an antiepileptic indicated as a monotherapy or adjunct therapy in the treatment of epilepsy.
- Generic Name
- Eslicarbazepine
- DrugBank Accession Number
- DB14575
- Background
Eslicarbazepine is an anti-epileptic medication available commercially as eslicarbazepine acetate.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Eslicarbazepine (DB14575)
- Weight
- Average: 254.2839
Monoisotopic: 254.105527702 - Chemical Formula
- C15H14N2O2
- Synonyms
- Eslicarbazepina
- Eslicarbazepine
- S(+)-Liscarbazepine
- External IDs
- BIA 2-194
- BIA-2-194
- CGP-13751
Pharmacology
- Indication
Not Available
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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.
Target Actions Organism AP2X purinoceptor 4 Not Available 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Eslicarbazepine. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Eslicarbazepine. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Eslicarbazepine. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Eslicarbazepine. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Eslicarbazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Eslicarbazepine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Eslicarbazepine. Adenine The metabolism of Eslicarbazepine can be decreased when combined with Adenine. Agomelatine The risk or severity of adverse effects can be increased when Agomelatine is combined with Eslicarbazepine. Albendazole The metabolism of Albendazole can be increased when combined with Eslicarbazepine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- ATC Codes
- N03AF04 — Eslicarbazepine
- Drug Categories
- Anticonvulsants
- Carboxamide Derivatives
- Cardiovascular Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Eslicarbazepine and prodrugs
- Heterocyclic Compounds, Fused-Ring
- Membrane Transport Modulators
- Nervous System
- Sodium Channel Blockers
- UGT1A1 Substrates
- Voltage-Gated Sodium Channel Blockers
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzenoid / Carbonic acid derivative / Carbonyl group / Dibenzazepine / Hydrocarbon derivative / Organic nitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- S5VXA428R4
- CAS number
- 104746-04-5
- 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
References
- General References
- External Links
- Human Metabolome Database
- HMDB0060702
- ChemSpider
- 8057180
- 1482502
- ChEBI
- 174358
- ChEMBL
- CHEMBL315985
- ZINC
- ZINC000000896938
- Wikipedia
- Eslicarbazepine_acetate
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Epilepsies 1 3 Completed Treatment Epilepsy With Simple or Complex Partial Onset Seizures 1 Not Available Completed Not Available Epilepsies 1
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 0.554 mg/mL ALOGPS logP 1.26 ALOGPS logP 1.73 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 14.1 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.56 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 72.29 m3·mol-1 Chemaxon Polarizability 26.45 Å3 Chemaxon Number of Rings 3 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 GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Targets
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- 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
- 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. [Article]
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
- FDA Approved Drug Products: Aptiom (eslicarbazepine acetate) tablets for oral use [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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- FDA Approved Drug Products: Aptiom (eslicarbazepine acetate) tablets for oral use [Link]
Drug created at July 20, 2018 21:43 / Updated at January 22, 2022 00:13