Identification
- Summary
Cenobamate is a small molecule drug indicated to treat partial onset seizures in adults.
- Brand Names
- Ontozry, XCopri, Xcopri 250 Mg Maintenance Pack, Xcopri Titration Pack - 12.5 Mg (14), 25 Mg (14) 28 Count
- Generic Name
- Cenobamate
- DrugBank Accession Number
- DB06119
- Background
Cenobamate, or YKP-3089, is an antiepileptic drug developed by SK Pharmaceuticals and used to treat partial onset seizures.1,3 The exact mechanism of action has not been described in the literature, though it positively modulates GABAA and inhibits voltage gated sodium channels.3
Cenobamate was granted FDA approval on 21 November 2019.3
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cenobamate (DB06119)
- Weight
- Average: 267.67
Monoisotopic: 267.0523023 - Chemical Formula
- C10H10ClN5O2
- Synonyms
- Cenobamate
- Cénobamate
- Cenobamato
- Cenobamatum
- External IDs
- YKP-3089
- YKP3089
Pharmacology
- Indication
Cenobamate is indicated for the treatment of partial onset seizures in adults.3
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 Partial-onset seizures •••••••••••• ••••• •••••• - 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
The mechanism of cenobamate is unknown, however it modulates GABAA and inhibit voltage gated sodium channels.3 Cenobamate is given once daily and so it has a long duration of action.3 The therapeutic window is wide as doses of 750mg can be well tolerated.2 Patients should be counselled regarding the risk of DRESS syndrome, QT interval shortening, suicidal behavior, and neurological adverse effects.3
- Mechanism of action
Cenobamate inhibits voltage gated sodium channels and is a positive GABAA modulator.3 However, the exact mechanism of action remains unknown.3 Inhibition of voltage gated sodium channels increases the threshold for generating action potentials and decreases the number of action potentials.1
- Absorption
Cenobamate is 88% orally bioavailable with a Tmax of 1-4 hours.3 A high fat meal does not significantly impact the pharmacokinetics of cenobamate.3
- Volume of distribution
The apparent volume of distribution of cenobamate is 40-50L.3
- Protein binding
Cenobamate is 60% protein bound in plasma, mainly serum albumin.3
- Metabolism
Data regarding the metabolism of cenobamate is lacking, however it is mostly glucuronidated by UGT2B7 and UGT2B4 or oxidized by a number of cytochromes.3
- Route of elimination
Cenobamate is 87.8% eliminated in the urine and 5.2% in the feces.3
- Half-life
The terminal half life of cenobamate is 50-60h.3
- Clearance
The apparent oral clearance of cenobamate is 0.45-0.63L/h for a 100-400mg/day dose.3
- 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
There is limited information regarding the signs, symptoms, and treatment of a cenobamate overdose.3 Symptomatic and supportive treatment is recommended and there is limited data on the utility of dialysis to remove cenobamate from blood.3
- 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 serum concentration of 1,2-Benzodiazepine can be decreased when it is combined with Cenobamate. Abametapir The serum concentration of Cenobamate can be increased when it is combined with Abametapir. Abatacept The metabolism of Cenobamate can be increased when combined with Abatacept. Abemaciclib The serum concentration of Abemaciclib can be decreased when it is combined with Cenobamate. Abiraterone The serum concentration of Abiraterone can be decreased when it is combined with Cenobamate. - Food Interactions
- Avoid alcohol. Alcohol may increase somnolence and sedation.
- Take with or without food.
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
- XCopri
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ontozry Tablet, film coated 50 mg Oral Angelini Pharma S.P.A 2021-04-20 Not applicable EU 
Ontozry Tablet, film coated 200 mg Oral Angelini Pharma S.P.A 2021-04-20 Not applicable EU Ontozry Tablet, film coated 150 mg Oral Angelini Pharma S.P.A 2021-04-20 Not applicable EU Ontozry Tablet, film coated 100 mg Oral Angelini Pharma S.P.A 2021-04-20 Not applicable EU Ontozry Tablet, film coated 50 mg Oral Angelini Pharma S.P.A 2021-04-20 Not applicable EU - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Xcopri Cenobamate (150 mg) + Cenobamate (200 mg) Kit; Tablet Oral Endo Ventures Ltd. Not applicable Not applicable Canada 
Xcopri Cenobamate (100 mg) + Cenobamate (50 mg) Kit; Tablet Oral Endo Ventures Ltd. Not applicable Not applicable Canada Xcopri Cenobamate (150 mg) + Cenobamate (200 mg) Kit; Tablet Oral Endo Ventures Ltd. Not applicable Not applicable Canada Xcopri Cenobamate (100 mg) + Cenobamate (150 mg) Kit; Tablet Oral Endo Ventures Ltd. Not applicable Not applicable Canada Xcopri Cenobamate (12.5 mg) + Cenobamate (25 mg) Kit; Tablet Oral Endo Ventures Ltd. Not applicable Not applicable Canada
Categories
- ATC Codes
- N03AX25 — Cenobamate
- Drug Categories
- Acids, Acyclic
- Anticonvulsants
- Benzene Derivatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Chlorobenzenes
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Inducers
- Cytochrome P-450 CYP2C8 Inducers (strength unknown)
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- GABA Modulators
- Nervous System
- Phenols
- UGT2B7 substrates
- Voltage-Gated Sodium Channel Blockers
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- P85X70RZWS
- CAS number
- 913088-80-9
- InChI Key
- GFHAXPJGXSQLPT-VIFPVBQESA-N
- InChI
- InChI=1S/C10H10ClN5O2/c11-8-4-2-1-3-7(8)9(18-10(12)17)5-16-14-6-13-15-16/h1-4,6,9H,5H2,(H2,12,17)/t9-/m0/s1
- IUPAC Name
- (1R)-1-(2-chlorophenyl)-2-(2H-1,2,3,4-tetrazol-2-yl)ethyl carbamate
- SMILES
- NC(=O)O[C@@H](CN1N=CN=N1)C1=C(Cl)C=CC=C1
References
- General References
- Nakamura M, Cho JH, Shin H, Jang IS: Effects of cenobamate (YKP3089), a newly developed anti-epileptic drug, on voltage-gated sodium channels in rat hippocampal CA3 neurons. Eur J Pharmacol. 2019 Jul 15;855:175-182. doi: 10.1016/j.ejphar.2019.05.007. Epub 2019 May 4. [Article]
- Kasteleijn-Nolst Trenite DGA, DiVentura BD, Pollard JR, Krauss GL, Mizne S, French JA: Suppression of the photoparoxysmal response in photosensitive epilepsy with cenobamate (YKP3089). Neurology. 2019 Aug 6;93(6):e559-e567. doi: 10.1212/WNL.0000000000007894. Epub 2019 Jul 10. [Article]
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- External Links
- ChemSpider
- 10136642
- 2265690
- ChEMBL
- CHEMBL3989949
- Wikipedia
- Cenobamate
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Active Not Recruiting Treatment Partial-Onset Seizures 1 3 Completed Treatment Partial Epilepsy 1 3 Enrolling by Invitation Treatment Primary Generalized Tonic Clonic Seizures in the Setting of Idiopathic Generalized Epilepsy 1 3 Recruiting Treatment Partial Epilepsy 1 3 Recruiting Treatment Primary Generalized Epilepsy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 100 MG Tablet, film coated Oral 150 MG Tablet, film coated Oral 200 MG Tablet, film coated Oral 50 MG Kit; tablet Oral Tablet Oral 100 mg Tablet Oral 12.5 mg Tablet Oral 150 mg Tablet Oral 200 mg Tablet Oral 25 mg Tablet Oral 50 mg Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Kit Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7598279 No 2009-10-06 2027-10-30 US 
US11654133 No 2019-06-16 2039-06-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 1.7mg/mL FDA Label logP 0.456 ChemSpider - Predicted Properties
Property Value Source Water Solubility 0.936 mg/mL ALOGPS logP 0.99 ALOGPS logP 1.66 Chemaxon logS -2.5 ALOGPS pKa (Strongest Acidic) 14.28 Chemaxon pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 95.92 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 76.43 m3·mol-1 Chemaxon Polarizability 24.35 Å3 Chemaxon Number of Rings 2 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 splash10-00kr-0940000000-92ad5eb3547e07d7dc2b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0khc-7490000000-be87323e9c3302a10f5e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-2590000000-c3be15d23d95543efba3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-bc3c61fd3b04c2705b32 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-1900000000-18c56a1cd118f9d1f748 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9200000000-0ddd5b151cdfdbab6753 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
- Gene Name
- UGT2B4
- Uniprot ID
- P06133
- Uniprot Name
- UDP-glucuronosyltransferase 2B4
- Molecular Weight
- 60512.035 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- General Function
- Steroid 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 oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- 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: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Oxygen binding
- 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 oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Steroid 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 oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- FDA Approved Drug Products: Xcopri Cenobamate Oral Tablets [Link]
Drug created at November 18, 2007 18:30 / Updated at February 21, 2021 18:51