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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-11-09 23:29:23 UTC
HMDB IDHMDB0014704
Secondary Accession Numbers
  • HMDB14704
Metabolite Identification
Common NameCarbamazepine
DescriptionCarbamazepine, also known as tegretol or carnexiv, belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines 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. Carbamazepine is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, carbamazepine participates in a number of enzymatic reactions. In particular, carbamazepine can be converted into 3-hydroxycarbamazepine through its interaction with the enzymes cytochrome P450 3A4, cytochrome P450 2B6, and cytochrome P450 3A7. In addition, carbamazepine can be converted into carbamazepine-10,11-epoxide; which is catalyzed by the enzymes cytochrome P450 2C8, cytochrome P450 3A4, cytochrome P450 3A5, cytochrome P450 3A7, and cytochrome P450 2C19. In humans, carbamazepine is involved in carbamazepine metabolism pathway. Carbamazepine is a potentially toxic compound. A dibenzoazepine that is 5H-dibenzoazepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.
Structure
Data?1582753211
Synonyms
ValueSource
5-Carbamoyl-5H-dibenz(b,F)azepineChEBI
5-Carbamoyl-5H-dibenz[b,F]azepineChEBI
5-Carbamoyl-5H-dibenzo(b,F)azepineChEBI
5-Carbamyl-5H-dibenzo(b,F)azepineChEBI
5H-Dibenz(b,F)azepine-5-carboxamideChEBI
CarbamazepenChEBI
CarbamazepinaChEBI
CarbamazepinumChEBI
CarnexivChEBI
EquetroKegg
TegretolKegg
CarbamezepineHMDB
NeurotolHMDB
AmizepineHMDB
Carbamazepine acetateHMDB
Carbamazepine anhydrousHMDB
Carbamazepine dihydrateHMDB
Carbamazepine hydrochlorideHMDB
Carbamazepine phosphateHMDB
EpitolHMDB
FinlepsinHMDB
Carbamazepine L-tartrate (4:1)HMDB
Carbamazepine sulfate (2:1)HMDB
CarbazepinHMDB
Chemical FormulaC15H12N2O
Average Molecular Weight236.2686
Monoisotopic Molecular Weight236.094963016
IUPAC Name2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
Traditional Name2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
CAS Registry Number298-46-4
SMILES
NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12
InChI Identifier
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)
InChI KeyFFGPTBGBLSHEPO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Azepine
  • Benzenoid
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP2.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM150.330932474
[M+H]+Not Available149.012http://allccs.zhulab.cn/database/detail?ID=AllCCS00000958
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP10(2.1) g/LALOGPS
logP10(2.77) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)15.96ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.33 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.89 m³·mol⁻¹ChemAxon
Polarizability25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.43131661259
DarkChem[M-H]-151.72631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CarbamazepineNC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C123809.0Standard polar33892256
CarbamazepineNC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C122170.2Standard non polar33892256
CarbamazepineNC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C122327.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carbamazepine,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C212243.7Semi standard non polar33892256
Carbamazepine,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C212248.4Standard non polar33892256
Carbamazepine,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C213415.9Standard polar33892256
Carbamazepine,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C2331.5Semi standard non polar33892256
Carbamazepine,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C2520.5Standard non polar33892256
Carbamazepine,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C3350.4Standard polar33892256
Carbamazepine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C212447.9Semi standard non polar33892256
Carbamazepine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C212444.3Standard non polar33892256
Carbamazepine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C213511.7Standard polar33892256
Carbamazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C2714.8Semi standard non polar33892256
Carbamazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C2849.9Standard non polar33892256
Carbamazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C3411.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carbamazepine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3970000000-8f03b4d1ea6cec6641ec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carbamazepine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-1910000000-4b2dc85e8da73b101ed22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-qTof , Positive-QTOFsplash10-000f-1940000000-9677ddf985ba43e768172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-qTof , Positive-QTOFsplash10-000f-0930000000-b2a70bea75cef0c245562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-qTof , Positive-QTOFsplash10-0006-2900000000-86f35079f274f4014c3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOFsplash10-000i-0090000000-be63f70e101a786a369b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOFsplash10-0006-0910000000-f171a56d3bbeaef24ff42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-a82def037961e9b94a9a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-484ce005b4ae5d01fc2a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-a6992953eac16c120e742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-7a1010be5231131649eb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-51ef94c86cca9b5417802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-000i-0490000000-4484ac1671912bc60ba92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-0006-0910000000-e5ca06888593ada95f152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-5742023f1e263fb400662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-f27fb9d17b228cc328b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-63c554c485fd1d1170822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-c6c89d3e663885fcc0802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-000i-0490000000-8a1d8d7b932f1b0ad45e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-0006-0910000000-843efaf5294cb110e0b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-7eb2855f73a1ed7291812017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine 10V, Positive-QTOFsplash10-000i-0290000000-926be8d54e58a26d40d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine 20V, Positive-QTOFsplash10-000f-0950000000-68b3fa7ce7380dc8311e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine 40V, Positive-QTOFsplash10-0006-1900000000-60a9fc188e8c79505dee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine 10V, Negative-QTOFsplash10-0006-8960000000-8aa13e4d27b1afb8662d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine 20V, Negative-QTOFsplash10-0006-2900000000-6d502f01257a774384bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine 40V, Negative-QTOFsplash10-0006-9500000000-3d22d3677d67ba94c4ac2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00564 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00564 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00564
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2457
KEGG Compound IDC06868
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbamazepine
METLIN IDNot Available
PubChem Compound2554
PDB IDNot Available
ChEBI ID3387
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
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 ]
General function:
Involved in monooxygenase 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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
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 ]
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
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 ]
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
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 ]
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
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 ]
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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 ]
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
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. 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 ]
General function:
Involved in ion channel activity
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 protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
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 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
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 ]