Identification

Name
Oxcarbazepine
Accession Number
DB00776  (APRD01308)
Type
Small Molecule
Groups
Approved
Description

Oxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom to the benzylcarboxamide group. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat partial seizures in epileptic children and adults.

Structure
Thumb
Synonyms
  • 10,11-Dihydro-10-oxo-5H-dibenz(b,F)azepine-5-carboxamide
  • OCBZ
  • Oxcarbamazepine
  • Oxcarbazepina
  • Oxcarbazepine
  • Oxcarbazepinum
External IDs
GP 47680 / GP-47680 / KIN-493 / SPN-804
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jamp-oxcarbazepineTablet150 mgOralJamp Pharma Corporation2015-06-08Not applicableCanada
Jamp-oxcarbazepineTablet300 mgOralJamp Pharma Corporation2015-06-08Not applicableCanada
Jamp-oxcarbazepineTablet600 mgOralJamp Pharma Corporation2015-06-08Not applicableCanada
Novo-oxcarbazepineTablet600 mgOralNovopharm LimitedNot applicableNot applicableCanada
Novo-oxcarbazepineTablet150 mgOralNovopharm LimitedNot applicableNot applicableCanada
Novo-oxcarbazepineTablet300 mgOralNovopharm LimitedNot applicableNot applicableCanada
OxcarbazepineTablet600 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
OxcarbazepineSuspension60 mg/mLOralSandoz2001-05-30Not applicableUs
OxcarbazepineTablet150 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
OxcarbazepineTablet300 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-oxcarbazepineTablet600 mgOralApotex Corporation2006-08-01Not applicableCanada
Apo-oxcarbazepineTablet300 mgOralApotex Corporation2006-08-01Not applicableCanada
Apo-oxcarbazepineTablet150 mgOralApotex Corporation2006-08-01Not applicableCanada
OxcarbazepineTablet, film coated150 mg/1OralJubilant Cadista Pharmaceuticals Inc.2015-01-152017-11-01Us
OxcarbazepineTablet, film coated150 mg/1OralAmerincan Health Packaging2007-11-092016-10-25Us
OxcarbazepineTablet, film coated300 mg/1OralRemedy Repack2011-05-202016-11-29Us
OxcarbazepineTablet, film coated300 mg/1OralPhysicians Total Care, Inc.2009-10-16Not applicableUs68462 0138 01 nlmimage10 ba085d72
OxcarbazepineTablet, film coated600 mg/1OralRemedy Repack2013-12-30Not applicableUs
OxcarbazepineSuspension300 mg/5mLOralPrecision Dose, Inc.2017-09-13Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralGolden State Medical Supply2008-04-09Not applicableUs
International/Other Brands
Actinium / Barzepin / Carbox / Deprectal / Lonazet / Oxalepsy / Oxetol / Oxpin / Oxrate / Oxypine / Pharozepine / Prolepsi / Timox / Trexapin / Trileptin
Categories
UNII
VZI5B1W380
CAS number
28721-07-5
Weight
Average: 252.268
Monoisotopic: 252.089877638
Chemical Formula
C15H12N2O2
InChI Key
CTRLABGOLIVAIY-UHFFFAOYSA-N
InChI
InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)
IUPAC Name
9-oxo-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide
SMILES
NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12

Pharmacology

Indication

For use as monotherapy or adjunctive therapy in the treatment of partial seizures in adults with epilepsy and as adjunctive therapy in the treatment of partial seizures in children ages 4-16 with epilepsy.

Structured Indications
Pharmacodynamics

Oxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom to the benzylcarboxamide group. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat the same conditions.

Mechanism of action

The exact mechanism by which oxcarbazepine exerts its anticonvulsant effect is unknown. It is known that the pharmacological activity of oxcarbazepine occurs primarily through its 10-monohydroxy metabolite (MHD). In vitro studies indicate an MHD-induced blockade of voltage-sensitive sodium channels, resulting in stabilization of hyperexcited neuronal membranes, inhibition of repetitive neuronal discharges, and diminution of propagation of synaptic impulses.

TargetActionsOrganism
ASodium channel protein type 5 subunit alpha
inhibitor
Human
Absorption

Completely absorbed following oral administration. Food has no effect on the rate and extent of absorption of oxcarbazepine. After single-dose administration of Trileptal tablets to healthy male volunteers under fasted conditions, the median tmax was 4.5 (range 3 to 13) hours. After single-dose administration of Trileptal oral suspension to healthy male volunteers under fasted conditions, the median tmax was six hours. Steady-state plasma concentrations of MHD are reached within 2-3 days in patients when Trileptal is given twice a day.

Volume of distribution
  • 49 L
Protein binding

Approximately 40% of the active 10-monohydroxy metabolite (MHD) is bound to serum proteins, predominantly to albumin. Neither oxcarbazepine nor its MHD binds with alpha-1-acid glycoprotein.

Metabolism

Oxcarbazepine is completely absorbed and extensively metabolized to its pharmacologically active 10-monohydroxy metabolite (MHD) by cytosolic enzymes. MHD is metabolized further by conjugation with glucuronic acid.

Route of elimination

Oxcarbazepine is cleared from the body mostly in the form of metabolites which are predominantly excreted by the kidneys. Fecal excretion accounts for less than 4% of the administered dose.

Half life

The half-life of the parent is about 2 hours, while the half-life of MHD is about 9 hours, so that MHD is responsible for most anti-epileptic activity.

Clearance
Not Available
Toxicity

Isolated cases of overdose with oxcarbazepine have been reported. The maximum dose taken was approximately 24,000 mg. All patients recovered with symptomatic treatment.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Carbamazepine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
HLA class I histocompatibility antigen, B-15 alpha chainHLA-B*15:02Not AvailableHLA-B*15ADR Directly StudiedPatients who carry this allele may be at an increased risk of Stevens-Johnson Syndrome and toxic epidermal necrolysis when treated with oxcarbazepine.Details

Interactions

Drug Interactions
DrugInteractionDrug group
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Oxcarbazepine.Approved
CarbamazepineThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Carbamazepine resulting in a loss in efficacy.Approved, Investigational
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Oxcarbazepine.Approved, Vet Approved
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Oxcarbazepine.Investigational, Withdrawn
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Oxcarbazepine.Approved
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Oxcarbazepine.Approved
CobicistatThe serum concentration of Cobicistat can be decreased when it is combined with Oxcarbazepine.Approved
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Oxcarbazepine.Approved
CyclopenthiazideThe risk or severity of adverse effects can be increased when Cyclopenthiazide is combined with Oxcarbazepine.Experimental
DesogestrelThe serum concentration of Desogestrel can be decreased when it is combined with Oxcarbazepine.Approved
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Oxcarbazepine.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
DolutegravirThe serum concentration of Dolutegravir can be decreased when it is combined with Oxcarbazepine.Approved
DrospirenoneThe serum concentration of Drospirenone can be decreased when it is combined with Oxcarbazepine.Approved
ElvitegravirThe serum concentration of Elvitegravir can be decreased when it is combined with Oxcarbazepine.Approved
Eslicarbazepine acetateThe risk or severity of adverse effects can be increased when Eslicarbazepine acetate is combined with Oxcarbazepine.Approved
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Oxcarbazepine.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Estramustine can be decreased when it is combined with Oxcarbazepine.Approved
Estrogens, esterifiedThe serum concentration of Estrogens, esterified can be decreased when it is combined with Oxcarbazepine.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Oxcarbazepine.Approved
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Oxcarbazepine.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Oxcarbazepine.Approved
Ethynodiol diacetateThe serum concentration of Ethynodiol diacetate can be decreased when it is combined with Oxcarbazepine.Approved
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
FosphenytoinThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Fosphenytoin resulting in a loss in efficacy.Approved
GestodeneThe serum concentration of Gestodene can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
HexestrolThe serum concentration of Hexestrol can be decreased when it is combined with Oxcarbazepine.Withdrawn
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Oxcarbazepine.Approved, Vet Approved
HydroflumethiazideThe risk or severity of adverse effects can be increased when Hydroflumethiazide is combined with Oxcarbazepine.Approved, Investigational
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Oxcarbazepine.Approved
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Oxcarbazepine.Approved
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
LynestrenolThe serum concentration of Lynestrenol can be decreased when it is combined with Oxcarbazepine.Investigational
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone acetate can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
MefloquineThe therapeutic efficacy of Oxcarbazepine can be decreased when used in combination with Mefloquine.Approved
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Oxcarbazepine.Approved
MethallenestrilThe serum concentration of Methallenestril can be decreased when it is combined with Oxcarbazepine.Experimental
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Oxcarbazepine.Approved
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Oxcarbazepine.Approved
MianserinThe therapeutic efficacy of Oxcarbazepine can be decreased when used in combination with Mianserin.Approved, Investigational
NorelgestrominThe serum concentration of Norelgestromin can be decreased when it is combined with Oxcarbazepine.Approved
NorgestimateThe serum concentration of Norgestimate can be decreased when it is combined with Oxcarbazepine.Approved
NorgestrelThe serum concentration of Norgestrel can be decreased when it is combined with Oxcarbazepine.Approved
OrlistatThe serum concentration of Oxcarbazepine can be decreased when it is combined with Orlistat.Approved, Investigational
PerampanelThe serum concentration of Oxcarbazepine can be increased when it is combined with Perampanel.Approved
PhenobarbitalThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Phenobarbital resulting in a loss in efficacy.Approved
PhenytoinThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Phenytoin resulting in a loss in efficacy.Approved, Vet Approved
PolythiazideThe risk or severity of adverse effects can be increased when Polythiazide is combined with Oxcarbazepine.Approved
QuinethazoneThe risk or severity of adverse effects can be increased when Quinethazone is combined with Oxcarbazepine.Approved
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Oxcarbazepine.Approved
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Oxcarbazepine.Approved
SelegilineOxcarbazepine may increase the serotonergic activities of Selegiline.Approved, Investigational, Vet Approved
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Oxcarbazepine.Approved
Synthetic Conjugated Estrogens, AThe serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Oxcarbazepine.Approved
TrichlormethiazideThe risk or severity of adverse effects can be increased when Trichlormethiazide is combined with Oxcarbazepine.Approved, Vet Approved
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Oxcarbazepine.Approved
Valproic AcidThe serum concentration of Oxcarbazepine can be decreased when it is combined with Valproic Acid.Approved, Investigational
Food Interactions
  • Take without regard to meals. Avoid alcohol.

References

Synthesis Reference

Judith Aronhime, "New crystal forms of oxcarbazepine and processes for their preparation." U.S. Patent US20030004154, issued January 02, 2003.

US20030004154
General References
  1. Mazza M, Della Marca G, Di Nicola M, Martinotti G, Pozzi G, Janiri L, Bria P, Mazza S: Oxcarbazepine improves mood in patients with epilepsy. Epilepsy Behav. 2007 May;10(3):397-401. Epub 2007 Feb 14. [PubMed:17300991]
External Links
Human Metabolome Database
HMDB14914
KEGG Drug
D00533
KEGG Compound
C07492
PubChem Compound
34312
PubChem Substance
46507580
ChemSpider
31608
BindingDB
34179
ChEBI
7824
ChEMBL
CHEMBL1068
Therapeutic Targets Database
DAP000528
PharmGKB
PA450732
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Oxcarbazepine
ATC Codes
N03AF02 — Oxcarbazepine
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
FDA label
Download (195 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentEpilepsies2
1CompletedTreatmentEpilepsies / Epilepsy, Localization Related1
1CompletedTreatmentEpilepsy, Localization Related1
1CompletedTreatmentSeizures2
1TerminatedSupportive CareCancers1
2RecruitingTreatmentDisseminated Sclerosis1
2, 3Active Not RecruitingTreatmentPartial onset seizure Epilepsy1
2, 3CompletedTreatmentSchizophrenic Disorders1
3Active Not RecruitingTreatmentAdverse Effects / Epilepsy, Localization Related1
3CompletedTreatmentAgitation Aggression in Dementia1
3CompletedTreatmentEpilepsies2
3CompletedTreatmentEpilepsies / Epilepsy, Localization Related1
3CompletedTreatmentEpilepsy, Localization Related2
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentEpilepsy, Localization Related1
4CompletedTreatmentBipolar Disorder (BD)2
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentEpilepsies1
4CompletedTreatmentEpilepsy, Partial Seizures2
4CompletedTreatmentOppositional Defiant Disorder1
4CompletedTreatmentPeripheral Nerve Injury (PNI) / Polyneuropathies / Postherpetic Neuralgia1
4CompletedTreatmentSeizures, Focal1
4CompletedTreatmentNeurocostal neuralgia / Spinal Cord Injuries (SCI)1
4RecruitingTreatmentBipolar Disorder (BD)1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedTreatmentAutism, Early Infantile1
Not AvailableCompletedTreatmentEpilepsies / Seizures3
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingNot AvailableEpilepsies1
Not AvailableUnknown StatusTreatmentPediatric Chronic Neuropathic Pain1

Pharmacoeconomics

Manufacturers
  • Ranbaxy laboratories ltd
  • Novartis pharmaceuticals corp
  • Apotex inc
  • Breckenridge pharmaceutical inc
  • Cadista pharmaceuticals inc
  • Glenmark generics ltd
  • Roxane laboratories inc
  • Sun pharmaceutical industries ltd
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa
Packagers
Dosage forms
FormRouteStrength
SuspensionOral300 mg/5mL
SuspensionOral60 mg/mL
TabletOral150 mg/1
TabletOral300 mg/1
TabletOral600 mg/1
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral600 mg/1
TabletOral150 mg
TabletOral300 mg
TabletOral600 mg
SuspensionOral60 mg
Prices
Unit descriptionCostUnit
OXcarbazepine 300 mg/5ml Suspension 250ml Bottle162.03USD bottle
Trileptal 600 mg tablet7.05USD tablet
Oxcarbazepine 600 mg tablet5.06USD tablet
Trileptal 300 mg tablet3.84USD tablet
Oxcarbazepine 300 mg tablet2.75USD tablet
Trileptal 150 mg tablet2.1USD tablet
Oxcarbazepine 150 mg tablet1.53USD tablet
Trileptal 300 mg/5ml Suspension0.79USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2277791No2008-11-182018-02-12Canada
US7037525Yes1998-08-122018-08-12Us
US8119148Yes2001-06-192021-06-19Us
US7910131No2007-04-132027-04-13Us
US9119791No2007-04-132027-04-13Us
US8821930No2007-04-132027-04-13Us
US8617600No2007-04-132027-04-13Us
US7722898No2007-04-132027-04-13Us
US9370525No2007-04-132027-04-13Us
US9351975No2007-04-132027-04-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)215.5 °CPhysProp
water solubility308 mg/L at 25 °C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))Not Available
logP1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 mg/mLALOGPS
logP1.76ALOGPS
logP1.82ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.92ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.4 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.56 m3·mol-1ChemAxon
Polarizability25.72 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9894
Blood Brain Barrier+0.9975
Caco-2 permeable+0.6299
P-glycoprotein substrateNon-substrate0.7157
P-glycoprotein inhibitor INon-inhibitor0.7193
P-glycoprotein inhibitor IINon-inhibitor0.9348
Renal organic cation transporterNon-inhibitor0.8176
CYP450 2C9 substrateNon-substrate0.773
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6022
CYP450 1A2 substrateNon-inhibitor0.7266
CYP450 2C9 inhibitorNon-inhibitor0.7371
CYP450 2D6 inhibitorNon-inhibitor0.9329
CYP450 2C19 inhibitorNon-inhibitor0.7428
CYP450 3A4 inhibitorNon-inhibitor0.8819
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8034
Ames testNon AMES toxic0.5078
CarcinogenicityNon-carcinogens0.9118
BiodegradationNot ready biodegradable0.8977
Rat acute toxicity1.9871 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9327
hERG inhibition (predictor II)Non-inhibitor0.869
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0pb9-0090000000-46d01e1171f998679d03
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f8i-1790000000-cd62672e7fa7c39f0be1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0kar-0690000000-cbc95a31913165d691a7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-2910000000-d1242af6b8148ffac3a9

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
Aryl alkyl ketones / Azepines / Benzenoids / Vinylogous amides / Isoureas / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Imines / Hydrocarbon derivatives
Substituents
Dibenzazepine / Aryl ketone / Aryl alkyl ketone / Azepine / Benzenoid / Vinylogous amide / Isourea / Ketone / Carboximidic acid derivative / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cyclic ketone, dibenzoazepine (CHEBI:7824)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function
This protein 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 pr...
Gene Name
SCN5A
Uniprot ID
Q14524
Uniprot Name
Sodium channel protein type 5 subunit alpha
Molecular Weight
226937.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Vohora D, Saraogi P, Yazdani MA, Bhowmik M, Khanam R, Pillai KK: Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs. Drugs Today (Barc). 2010 Apr;46(4):265-77. doi: 10.1358/dot.2010.46.4.1445795. [PubMed:20502724]

Enzymes

Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34