Identification

Name
Carbamazepine
Accession Number
DB00564  (APRD00337)
Type
Small Molecule
Groups
Approved, Investigational
Description

An anticonvulsant used to control grand mal and psychomotor or focal seizures. Its mode of action is not fully understood, but some of its actions resemble those of phenytoin; although there is little chemical resemblance between the two compounds, their three-dimensional structure is similar.

Structure
Thumb
Synonyms
  • 5-Carbamoyl-5H-dibenz(b,f)azepine
  • 5-carbamoyl-5H-dibenz[b,f]azepine
  • 5-Carbamoyl-5H-dibenzo(b,f)azepine
  • 5-Carbamyl-5H-dibenzo(b,f)azepine
  • 5H-Dibenz(b,f)azepine-5-carboxamide
  • Carbamazepen
  • Carbamazepin
  • Carbamazepina
  • Carbamazépine
  • Carbamazepinum
  • CBZ
External IDs
G 32 883 / G-32883 / GEIGY 32883 / NSC-169864 / SPD417
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Carbamazepine Tab 200mgTablet200 mgOralApotex Corporation1980-12-31Not applicableCanada
CarbamazepineTablet, extended release200 mg/1OralKaiser Foundations Hospitals2009-10-282012-06-30Us
CarbamazepineTablet, chewable100 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2008-01-29Not applicableUs
CarbamazepineTablet100 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2008-01-29Not applicableUs
CarbamazepineTablet300 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2008-01-29Not applicableUs
CarbamazepineTablet200 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2008-01-29Not applicableUs
CarbamazepineTablet400 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2008-01-29Not applicableUs
Carbamazepine 200 Tab 200mgTablet200 mgOralPro Doc Limitee1982-12-312013-07-15Canada
Carbamazepine 200mg TabletsTablet200 mgOralLaboratoires Confab IncNot applicableNot applicableCanada
Carbamazepine CRTablet, extended release400 mgOralPro Doc Limitee2013-11-21Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-carbamazepine CRTablet, extended release400 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-carbamazepine CRTablet, extended release200 mgOralApotex CorporationNot applicableNot applicableCanada
Bio-carbamazepineTablet200 mgOralBiomed Pharma2003-08-202010-03-16Canada
CarbamazepineTablet200 mg/1OralAmerincan Health Packaging2014-04-01Not applicableUs
CarbamazepineTablet, chewable100 mg/1OralTorrent Pharmaceuticals Limited2009-08-26Not applicableUs
CarbamazepineCapsule, extended release300 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2013-06-21Not applicableUs
CarbamazepineTablet200 mg/1OralA-S Medication Solutions1996-10-03Not applicableUs50090 038420180907 15195 7j1nxv
CarbamazepineTablet, extended release200 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2009-03-31Not applicableUs51672 4124 01 nlmimage10 33041990
CarbamazepineTablet, chewable200 mg/1OralPreferreed Pharmaceuticals Inc.2012-04-23Not applicableUs
CarbamazepineTablet200 mg/1OralStat Rx USA2009-12-08Not applicableUs
International/Other Brands
Actebral (Sanofi-Aventis) / Anleptic (Square) / Biston (Zentiva) / Carbamat (AstraZeneca) / Neurotop (Gerot) / TEGretol Chewtabs / TEGretol-CR (Novartis) / TEGretol-XR (Novartis) / Teril (Taro) / Timonil (Desitin) / Versitol (Micro Synapse) / Versizur (Micro Labs)
Categories
UNII
33CM23913M
CAS number
298-46-4
Weight
Average: 236.2686
Monoisotopic: 236.094963016
Chemical Formula
C15H12N2O
InChI Key
FFGPTBGBLSHEPO-UHFFFAOYSA-N
InChI
InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)
IUPAC Name
2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
SMILES
NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12

Pharmacology

Indication

For the treatment of epilepsy and pain associated with true trigeminal neuralgia.

Associated Conditions
Pharmacodynamics

Carbamazepine, an anticonvulsant structurally similar to tricyclic antidepressants, is used to treat partial seizures, tonic-clonic seizures, pain of neurologic origin such as trigeminal neuralgia, and psychiatric disorders including manic-depressive illness and aggression due to dementia. The response to carbamazepine is variable and may be due to its variable transport, especially across the blood-brain-barrier. The transporter that may confer drug resistance is RALBP1.

Mechanism of action

Carbamazepine inhibits sustained repetitive firing by blocking use-dependent sodium channels. Pain relief is believed to be associated with blockade of synaptic transmission in the trigeminal nucleus and seizure control with reduction of post-tetanic potentiation of synaptic transmission in the spinal cord. Carbamazepine also possesses anticholinergic, central antidiuretic, antiarrhythmic, muscle relaxant, antidepressant (possibly through blockade of norepinephrine release), sedative, and neuromuscular-blocking properties.

TargetActionsOrganism
ASodium channel protein type 5 subunit alpha
inhibitor
Human
UNeuronal acetylcholine receptor subunit alpha-4Not AvailableHuman
UNeuronal acetylcholine receptor subunit beta-2Not AvailableHuman
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
Absorption

In clinical studies, carbamazepine suspension, conventional tablets, and extended-release tablets delivered equivalent amounts of drug to the systemic circulation. However, it has been observed that the suspension is somewhat faster absorbed. Furthermore, the extended-release tablet is slightly slower than the conventional tablet. The bioavailability of the extended-release tablet is 89%, compared to the suspension. Plasma levels of carbamazepine are variable. The time to peak concentration for the different formulations are as follows: Suspension = 1.5 hours; Conventional tablets = 4-5 hours; Extended-release tablets = 3-12 hours.

Volume of distribution
Not Available
Protein binding

76% bound to plasma proteins.

Metabolism

Hepatic. CYP3A4 is the primary isoform responsible for the formation of carbamazepine-10,11-epoxide. This metabolite is active and shown to be equipotent to carbamazepine as an anticonvulsant. Carbamazepine is more rapidly metabolized to the aforementioned metabolite in younger patients than in adults. It also undergoes glucuronidation via UGT2B7, however this finding has been disputed.

Route of elimination

72% of the dose is in the urine while 28% is in the feces. Hydroxylated and conjugated metabolites are largely what was recovered in the urine. 3% of the dose is recovered as unchanged carbamazepine.

Half life

Initial half-life values range from 25-65 hours, decreasing to 12-17 hours on repeated doses.

Clearance
Not Available
Toxicity

Mild ingestions cause vomiting, drowsiness, ataxia, slurred speech, nystagmus, dystonic reactions, and hallucinations. Severe intoxications may produce coma, seizures, respiratory depression, and hypotension

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
Heat shock 70 kDa protein 1-like---(C;T) / (T;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.Details
Heat shock 70 kDa protein 1A/1B---(C;C) / (C;G) / (C;T)C allele / C alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.Details
HLA class I histocompatibility antigen, B-15 alpha chain---(G;T) / (T;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.Details
HLA class I histocompatibility antigen, A-31 alpha chain---(C;G) / (G;G)G alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.Details
Promotilin---(A;A) / (A;C)A alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.Details
Sodium channel protein type 1 subunit alpha---(A;A) / (A;G)IVS5N + 5 G>AEffect Directly StudiedPatients with this genotype have increased resistance to the anti-epileptic effects of carbamazepine.Details
Flotillin-1HLA-B*1502(C;G) / (G;G)G > C / G > CADR Directly StudiedTaiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine.Details
Mucin-21HLA-B*1502(A;G) / (G;G)G>A / G>AADR Directly StudiedTaiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine.Details
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 carbamazepine.Details
HLA class I histocompatibility antigen, A-3 alpha chainHLA-A*3101(A;T) / (T;T)A > TADR Directly StudiedPatients who carry this genotype in HLA-A are at a higher risk of experiencing a hypersensitivity reaction to carbamazepine.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Carbamazepine can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Carbamazepine can be decreased when combined with (S)-Warfarin.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Carbamazepine is combined with 2-Methoxyethanol.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Carbamazepine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Carbamazepine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be decreased when it is combined with Carbamazepine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Carbamazepine is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of Carbamazepine can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Carbamazepine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Carbamazepine.
Food Interactions
  • Avoid alcohol.
  • Avoid taking grapefruit or grapefruit juice throughout treatment.
  • Grapefruit can significantly increase serum levels of this product.
  • Take with food, increases availability and reduces irritation.

References

Synthesis Reference

Ketan Dhansukhlal Vyas, Wajid Sajjad Jafri, Ashok Krishna Kulkarni, "Process for preparing carbamazepine from iminostilbene." U.S. Patent US6245908, issued February, 1998.

US6245908
General References
  1. Staines AG, Coughtrie MW, Burchell B: N-glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther. 2004 Dec;311(3):1131-7. Epub 2004 Aug 3. [PubMed:15292462]
  2. Sisodiya SM, Goldstein DB: Drug resistance in epilepsy: more twists in the tale. Epilepsia. 2007 Dec;48(12):2369-70. [PubMed:18088268]
External Links
Human Metabolome Database
HMDB0014704
KEGG Drug
D00252
KEGG Compound
C06868
PubChem Compound
2554
PubChem Substance
46507583
ChemSpider
2457
BindingDB
50003659
ChEBI
3387
ChEMBL
CHEMBL108
Therapeutic Targets Database
DAP000129
PharmGKB
PA448785
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Carbamazepine
ATC Codes
N03AF01 — Carbamazepine
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
FDA label
Download (55.9 KB)
MSDS
Download (71.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableBio-equivalence Study / Fed Conditions1
1CompletedNot AvailableHealthy Volunteers3
1CompletedNot AvailableHealthy Volunteers / Pharmacology, Clinical1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentEpilepsies2
1CompletedTreatmentHealthy Participants1
1CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentCocaine-Related Disorders / Substance-Related Disorders2
2CompletedTreatmentEpilepsies / Infantile Spasms (IS)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentPhotosensitive Epilepsy1
2RecruitingTreatmentAlpha-1-Antitrypsin Deficiency / Liver Cirrhosis1
2Unknown StatusPreventionChemotherapy-Induced Nausea and Vomiting (CINV)1
2, 3CompletedTreatmentTrigeminal Neuralgia (TN)1
3CompletedNot AvailableSeizures1
3CompletedTreatmentEpilepsies3
3CompletedTreatmentEpilepsies / Seizures1
3CompletedTreatmentEpilepsies / Partial onset seizure Epilepsy1
3CompletedTreatmentManic or Mixed Episode Associated With Bipolar I Disorder1
3RecruitingTreatmentDementias1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3Unknown StatusTreatmentSeizures, Epileptic / Strokes1
4CompletedNot AvailableConvulsions / Epilepsies / Osteopenia / Osteoporosis / Seizures1
4CompletedTreatmentAlcohol Dependence1
4CompletedTreatmentBipolar Disorder (BD)2
4CompletedTreatmentBipolar Disorder (BD) / Mania1
4CompletedTreatmentBronchial Asthma2
4CompletedTreatmentCocaine-Related Disorders / Substance-Related Disorders1
4CompletedTreatmentDepression, Bipolar1
4CompletedTreatmentEpilepsies5
4CompletedTreatmentEpilepsy, Localization Related1
4CompletedTreatmentNeurocostal neuralgia / Pain, Neuropathic1
4CompletedTreatmentSeizures, Focal1
4Enrolling by InvitationTreatmentErythromelalgia1
4Not Yet RecruitingTreatmentEpilepsy, Localization Related1
4RecruitingNot AvailableEpilepsies1
4RecruitingTreatmentBipolar Disorder (BD)1
4RecruitingTreatmentEpilepsies1
4Unknown StatusTreatmentBipolar Disorder (BD)1
Not AvailableCompletedNot AvailableEpilepsies2
Not AvailableCompletedBasic ScienceHealthy Male Volunteers1
Not AvailableCompletedTreatmentTraumatic Brain Injury (TBI)1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingNot AvailableEpilepsies1
Not AvailableUnknown StatusTreatmentAdults With Tonic Clonic Seizures and/or Partial Seizures1
Not AvailableUnknown StatusTreatmentCarpal Tunnel Syndrome (CTS) / Multiple Excitability Test1

Pharmacoeconomics

Manufacturers
  • Shire development inc
  • Validus pharmaceuticals inc
  • Taro pharmaceutical industries ltd
  • Wockhardt eu operations (swiss) ag
  • Novartis pharmaceuticals corp
  • Taro pharmaceuticals usa inc
  • Cadista pharmaceuticals inc
  • Torrent pharmaceuticals ltd
  • Teva pharmaceuticals usa inc
  • Actavis elizabeth llc
  • Apotex inc etobicoke site
  • Inwood laboratories inc sub forest laboratories inc
  • Pliva inc
  • Usl pharma inc
  • Warner chilcott div warner lambert co
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Ciba Geigy Ltd.
  • Coupler Enterprises Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DSM Corp.
  • Goldline Laboratories Inc.
  • Hawkins Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Inwood Labs
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Patheon Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Packaging Center
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Precision Dose Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Sandoz
  • Shire Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • Torrent Pharmaceuticals
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Validus Pharmaceuticals
  • Vangard Labs Inc.
  • Vistapharm Inc.
  • Wellspring Pharmaceutical
  • Wockhardt Ltd.
  • Xactdose Inc.
Dosage forms
FormRouteStrength
SuspensionOral100 mg/5mL
SuspensionOral200 mg/10mL
TabletOral100 mg/1
TabletOral200 mg/1
TabletOral300 mg/1
TabletOral400 mg/1
Tablet, chewableOral100 mg/1
Tablet, chewableOral200 mg/1
Tablet, extended releaseOral400 mg/1
Injection, powder, for solutionIntravenous10 mg/1mL
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral200 mg/1
Capsule, extended releaseOral300 mg/1
Tablet, chewableOral100 mg
Tablet, chewableOral200 mg
Tablet, extended releaseOral200 mg
Tablet, extended releaseOral400 mg
TabletOral200 mg
SuspensionOral100 mg
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral200 mg/1
Prices
Unit descriptionCostUnit
Equetro 300 mg capsule2.65USD capsule
TEGretol XR 400 mg 12 Hour tablet2.42USD tablet
Carbamazepine powder2.26USD g
Tegretol xr 400 mg tablet2.19USD tablet
Carbatrol 100 mg 12 Hour Capsule2.18USD capsule
Equetro 200 mg capsule2.15USD capsule
CarBAMazepine 400 mg 12 Hour tablet2.05USD tablet
Carbatrol 300 mg 12 Hour Capsule1.95USD capsule
Carbatrol 200 mg 12 Hour Capsule1.92USD capsule
Carbatrol er 100 mg capsule1.84USD capsule
Carbatrol er 200 mg capsule1.84USD capsule
Carbatrol er 300 mg capsule1.84USD capsule
Equetro 100 mg capsule1.74USD capsule
TEGretol XR 200 mg 12 Hour tablet1.45USD tablet
Tegretol xr 200 mg tablet1.1USD tablet
CarBAMazepine 200 mg 12 Hour tablet1.03USD tablet
TEGretol XR 100 mg 12 Hour tablet0.97USD tablet
Tegretol Cr 400 mg Sustained-Release Tablet0.84USD tablet
Tegretol 200 mg tablet0.75USD tablet
Tegretol xr 100 mg tablet0.55USD tablet
Tegretol Cr 200 mg Sustained-Release Tablet0.42USD tablet
Mylan-Carbamazepine Cr 400 mg Sustained-Release Tablet0.4USD tablet
Pms-Carbamazepine-Cr 400 mg Sustained-Release Tablet0.4USD tablet
Sandoz Carbamazepine Cr 400 mg Sustained-Release Tablet0.4USD tablet
Tegretol 200 mg Chewable Tablet0.34USD tablet
Carbamazepine 200 mg tablet0.31USD tablet
Epitol 200 mg tablet0.3USD tablet
CarBAMazepine 100 mg Chew Tabs0.25USD tab
Mylan-Carbamazepine Cr 200 mg Sustained-Release Tablet0.2USD tablet
Pms-Carbamazepine-Cr 200 mg Sustained-Release Tablet0.2USD tablet
Sandoz Carbamazepine Cr 200 mg Sustained-Release Tablet0.2USD tablet
Tegretol 100 mg Chewable Tablet0.17USD tablet
CarBAMazepine 100 mg/5ml Suspension0.16USD ml
Pms-Carbamazepine 200 mg Chewable Tablet0.16USD tablet
Sandoz Carbamazepine 200 mg Chewable Tablet0.16USD tablet
Taro-Carbamazepine 200 mg Chewable Tablet0.16USD tablet
Apo-Carbamazepine 200 mg Tablet0.08USD tablet
Novo-Carbamaz 200 mg Tablet0.08USD tablet
Nu-Carbamazepine 200 mg Tablet0.08USD tablet
Pms-Carbamazepine 100 mg Chewable Tablet0.08USD tablet
Sandoz Carbamazepine 100 mg Chewable Tablet0.08USD tablet
Taro-Carbamazepine 100 mg Chewable Tablet0.08USD tablet
Tegretol 20 mg/ml Suspension0.08USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5284662No1994-02-082011-02-08Us
US5912013No1999-06-152016-06-15Us
US6977253No2005-12-202024-05-19Us
US7635773No2009-12-222029-03-13Us
US8410077No2013-04-022029-03-13Us
US9493582No2016-11-152033-02-27Us
US9629797No2017-04-252028-11-10Us
US9770407No2017-09-262028-11-10Us
US9750822No2017-09-052029-03-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)204-206Schindier, W.; U.S. Patent 2,948,718; August 9, 1960; assigned to Geigy Chemical Corporation.
water solubility17.7 mg/LNot Available
logP2.45DAL POZZO,A ET AL. (1989)
Predicted Properties
PropertyValueSource
Water Solubility0.152 mg/mLALOGPS
logP2.1ALOGPS
logP2.77ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.96ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.33 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.89 m3·mol-1ChemAxon
Polarizability25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9962
Blood Brain Barrier+0.9958
Caco-2 permeable+0.6538
P-glycoprotein substrateNon-substrate0.6466
P-glycoprotein inhibitor INon-inhibitor0.8748
P-glycoprotein inhibitor IINon-inhibitor0.8381
Renal organic cation transporterNon-inhibitor0.8177
CYP450 2C9 substrateNon-substrate0.7466
CYP450 2D6 substrateSubstrate0.884
CYP450 3A4 substrateNon-substrate0.6204
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8222
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7358
Ames testNon AMES toxic0.5554
CarcinogenicityNon-carcinogens0.8848
BiodegradationNot ready biodegradable0.978
Rat acute toxicity2.1131 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9653
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.72 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-1910000000-4b2dc85e8da73b101ed2
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-QTOF , positiveLC-MS/MSsplash10-000i-0090000000-be63f70e101a786a369b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0910000000-f171a56d3bbeaef24ff4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-a82def037961e9b94a9a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-484ce005b4ae5d01fc2a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-a6992953eac16c120e74
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-7a1010be5231131649eb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-51ef94c86cca9b541780
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0490000000-4484ac1671912bc60ba9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0910000000-e5ca06888593ada95f15
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-5742023f1e263fb40066
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-f27fb9d17b228cc328b8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-63c554c485fd1d117082
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-c6c89d3e663885fcc080
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0490000000-8a1d8d7b932f1b0ad45e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0910000000-843efaf5294cb110e0b9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-7eb2855f73a1ed729181
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-8a4709b0e827021ff3f9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-1df850c9bb30bdd7c2e8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-13a692d2c13ee8b68c2b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-83772c2db35186bf1ecc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-b290173294be98d66006
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0910000000-19e4159c1f593ac5b7d2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-771ef8e73ddaa54860b8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0900000000-c125faa4ad9fe14be82e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0900000000-3a27cd51304e5edfed4d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000l-0790000000-46b6d4ec5e29491b5c70
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000l-0790000000-b259164c7da3679c2598
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000f-0930000000-b2a70bea75cef0c24556
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000f-1940000000-9677ddf985ba43e76817
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-2900000000-86f35079f274f4014c3d
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-ff23826da10bdf95f991
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-25b86b23833bee39c759
1H NMR Spectrum1D NMRNot Applicable

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 / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Dibenzazepine / Azepine / Benzenoid / Urea / Carbonic acid derivative / Azacycle / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
ureas, dibenzoazepine (CHEBI:3387)

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. Yang YC, Huang CS, Kuo CC: Lidocaine, carbamazepine, and imipramine have partially overlapping binding sites and additive inhibitory effect on neuronal Na+ channels. Anesthesiology. 2010 Jul;113(1):160-74. doi: 10.1097/ALN.0b013e3181dc1dd6. [PubMed:20526191]
  4. Yang YC, Kuo CC: Inhibition of Na(+) current by imipramine and related compounds: different binding kinetics as an inactivation stabilizer and as an open channel blocker. Mol Pharmacol. 2002 Nov;62(5):1228-37. [PubMed:12391287]
  5. Lipkind GM, Fozzard HA: Molecular model of anticonvulsant drug binding to the voltage-gated sodium channel inner pore. Mol Pharmacol. 2010 Oct;78(4):631-8. doi: 10.1124/mol.110.064683. Epub 2010 Jul 19. [PubMed:20643904]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Ortells MO, Barrantes GE: Molecular modelling of the interactions of carbamazepine and a nicotinic receptor involved in the autosomal dominant nocturnal frontal lobe epilepsy. Br J Pharmacol. 2002 Jul;136(6):883-95. [PubMed:12110613]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Ortells MO, Barrantes GE: Molecular modelling of the interactions of carbamazepine and a nicotinic receptor involved in the autosomal dominant nocturnal frontal lobe epilepsy. Br J Pharmacol. 2002 Jul;136(6):883-95. [PubMed:12110613]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Curator comments
weak activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [PubMed:14977870]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [PubMed:18537577]
  2. Levy RH: Cytochrome P450 isozymes and antiepileptic drug interactions. Epilepsia. 1995;36 Suppl 5:S8-13. [PubMed:8806399]
  3. Cazali N, Tran A, Treluyer JM, Rey E, d'Athis P, Vincent J, Pons G: Inhibitory effect of stiripentol on carbamazepine and saquinavir metabolism in human. Br J Clin Pharmacol. 2003 Nov;56(5):526-36. [PubMed:14651727]
  4. 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]
  5. Chen L, Boinpally R, Gad N, Greenberg WM, Wangsa J, Periclou A, Ghahramani P: Evaluation of Cytochrome P450 (CYP) 3A4-Based Interactions of Levomilnacipran with Ketoconazole, Carbamazepine or Alprazolam in Healthy Subjects. Clin Drug Investig. 2015 Oct;35(10):601-12. doi: 10.1007/s40261-015-0318-2. [PubMed:26315684]
  6. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  7. de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [PubMed:22332980]
  8. Flockhart Table - Indiana University [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
  1. Cazali N, Tran A, Treluyer JM, Rey E, d'Athis P, Vincent J, Pons G: Inhibitory effect of stiripentol on carbamazepine and saquinavir metabolism in human. Br J Clin Pharmacol. 2003 Nov;56(5):526-36. [PubMed:14651727]
  2. Kato Y, Fujii T, Mizoguchi N, Takata N, Ueda K, Feldman MD, Kayser SR: Potential interaction between ritonavir and carbamazepine. Pharmacotherapy. 2000 Jul;20(7):851-4. [PubMed:10907977]
  3. Mesdjian E, Seree E, Charvet B, Mirrione A, Bourgarel-Rey V, Desobry A, Barra Y: Metabolism of carbamazepine by CYP3A6: a model for in vitro drug interactions studies. Life Sci. 1999;64(10):827-35. [PubMed:10096433]
  4. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  5. Liu A, Wang C, Hehir M, Zhou T, Yang J: In vivo induction of CYP in mice by carbamazepine is independent on PXR. Pharmacol Rep. 2015 Apr;67(2):299-304. doi: 10.1016/j.pharep.2014.10.002. Epub 2014 Oct 18. [PubMed:25712654]
  6. de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [PubMed:22332980]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423]
  2. 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]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  4. de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [PubMed:22332980]
  5. Masubuchi Y, Nakano T, Ose A, Horie T: Differential selectivity in carbamazepine-induced inactivation of cytochrome P450 enzymes in rat and human liver. Arch Toxicol. 2001 Nov;75(9):538-43. [PubMed:11760814]
  6. Jerling M, Lindstrom L, Bondesson U, Bertilsson L: Fluvoxamine inhibition and carbamazepine induction of the metabolism of clozapine: evidence from a therapeutic drug monitoring service. Ther Drug Monit. 1994 Aug;16(4):368-74. [PubMed:7974626]
  7. CYP table [Link]
  8. CP450 drug interactions [File]
Kind
Protein
Organism
Human
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 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. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  3. de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [PubMed:22332980]
  4. Tegretol FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
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. Lakehal F, Wurden CJ, Kalhorn TF, Levy RH: Carbamazepine and oxcarbazepine decrease phenytoin metabolism through inhibition of CYP2C19. Epilepsy Res. 2002 Dec;52(2):79-83. [PubMed:12458024]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  3. de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [PubMed:22332980]
  4. Indiana University - Department of Medicine Clinical Pharmacology [Link]
  5. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Human
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
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 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. Pearce RE, Vakkalagadda GR, Leeder JS: Pathways of carbamazepine bioactivation in vitro I. Characterization of human cytochromes P450 responsible for the formation of 2- and 3-hydroxylated metabolites. Drug Metab Dispos. 2002 Nov;30(11):1170-9. [PubMed:12386121]
  3. de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [PubMed:22332980]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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]
  2. Usui T, Saitoh Y, Komada F: Induction of CYP3As in HepG2 cells by several drugs. Association between induction of CYP3A4 and expression of glucocorticoid receptor. Biol Pharm Bull. 2003 Apr;26(4):510-7. [PubMed:12673034]
  3. Park PW, Seo YH, Ahn JY, Kim KA, Park JY: Effect of CYP3A5*3 genotype on serum carbamazepine concentrations at steady-state in Korean epileptic patients. J Clin Pharm Ther. 2009 Oct;34(5):569-74. doi: 10.1111/j.1365-2710.2009.01057.x. [PubMed:19744012]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 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
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
  1. Kim KA, Oh SO, Park PW, Park JY: Effect of probenecid on the pharmacokinetics of carbamazepine in healthy subjects. Eur J Clin Pharmacol. 2005 Jun;61(4):275-80. Epub 2005 May 25. [PubMed:15915352]
  2. Spina E, Pisani F, Perucca E: Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet. 1996 Sep;31(3):198-214. doi: 10.2165/00003088-199631030-00004. [PubMed:8877250]
  3. de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [PubMed:22332980]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inducer
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. Interactions [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. [PubMed:11297522]
  2. Owen A, Pirmohamed M, Tettey JN, Morgan P, Chadwick D, Park BK: Carbamazepine is not a substrate for P-glycoprotein. Br J Clin Pharmacol. 2001 Apr;51(4):345-9. [PubMed:11318771]
  3. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524]
  4. Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein. Neuropharmacology. 2007 Feb;52(2):333-46. Epub 2006 Oct 10. [PubMed:17045309]
  5. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transmembrane transporter activity
Specific Function
Can activate specifically hydrolysis of GTP bound to RAC1 and CDC42, but not RALA. Mediates ATP-dependent transport of S-(2,4-dinitrophenyl)-glutathione (DNP-SG) and doxorubicin (DOX) and is the ma...
Gene Name
RALBP1
Uniprot ID
Q15311
Uniprot Name
RalA-binding protein 1
Molecular Weight
76062.86 Da
References
  1. Awasthi S, Hallene KL, Fazio V, Singhal SS, Cucullo L, Awasthi YC, Dini G, Janigro D: RLIP76, a non-ABC transporter, and drug resistance in epilepsy. BMC Neurosci. 2005 Sep 27;6:61. [PubMed:16188027]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Ufer M, Mosyagin I, Muhle H, Jacobsen T, Haenisch S, Hasler R, Faltraco F, Remmler C, von Spiczak S, Kroemer HK, Runge U, Boor R, Stephani U, Cascorbi I: Non-response to antiepileptic pharmacotherapy is associated with the ABCC2 -24C>T polymorphism in young and adult patients with epilepsy. Pharmacogenet Genomics. 2009 May;19(5):353-62. [PubMed:19415824]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2018 13:39