General Information of Drug (ID: DR0270)
Drug Name
Carbamazepine
Prodrug Info Carbamazepine is the prodrug of 10,11-Epoxycarbamazepine
Synonyms
Calepsin; Carbamazepen; Carbamazepin; Carbamazepina; Carbamazepinum; Carbamezepine; Carbatrol; Carbazepine; Carnexiv; Amizepin; Bipotrol; Biston; Epitol; Equetro; Finlepsin; Geigy 32883; Karbamazepin; Neurotol; Stazepin; Stazepine; Tegretal; Tegretol; Tegretol-Xr; Telesmin; Timonil; carbamazepine; 298-46-4; 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; 5H-Dibenz[b,f]azepine-5-carboxamide; 5H-Dibenzo[b,f]azepine-5-carboxamide; Lexin; Teril
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 236.27 Topological Polar Surface Area 46.3
Heavy Atom Count 18 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
2554
PubChem SID
9085 ; 442467 ; 621391 ; 855967 ; 866528 ; 3154113 ; 5051955 ; 7847318 ; 7978855 ; 8149231 ; 8151689 ; 10321205 ; 10517602 ; 11109646 ; 11110939 ; 11110940 ; 11207111 ; 11335563 ; 11338925 ; 11360802 ; 11362930 ; 11365492 ; 11368054 ; 11371249 ; 11373863 ; 11376216 ; 11461774 ; 11466080 ; 11467200 ; 11483906 ; 11485860 ; 11487941 ; 11490141 ; 11492077 ; 11493910 ; 11514284 ; 14847331 ; 17389547 ; 17404855 ; 24278084 ; 24893120 ; 26611636 ; 26679702 ; 26747063 ; 26747064 ; 26751576 ; 29221715 ; 46507583 ; 47216705 ; 47365117
ChEBI ID
CHEBI:3387
CAS Number
298-46-4
TTD Drug ID
D04MSM
Formula
C15H12N2O
Canonical SMILES
C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N
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)
InChIKey
FFGPTBGBLSHEPO-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
10,11-Epoxycarbamazepine DM000722
2555
Oxidation - 10,11-Epoxidation 1 [8]
3-hydroxycarbamazepine DM000725
135290
Oxidation - 3-Hydroxylation 1 [8]
Carbamazepine 2,3-epoxide DM000718
145722035
Unclear 1 [8]
Carbamazepine N-glucuronide DM000727
83870
Conjugation - N-Glucuronidation 1 [8]
10,11-Dihydroxycarbamazepine DM000723
83852
Unclear 2 [8]
2-hydroxycarbamazepine DM000719
129274
Unclear 2 [8]
9-hydroxymethyl-10-carbamaoyl acridan DM000724 N. A. Unclear 2 [11]
Iminoquinone DM000721
24892806
Unclear 2 [8]
2-hydroxyiminostilbene DM000720
13103864
Unclear 3 [8]
Iminoquinone DM000721
24892806
Unclear 4 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002587 Carbamazepine Carbamazepine 2,3-epoxide Unclear Unclear [8]
MR002588 Carbamazepine 10,11-Epoxycarbamazepine Oxidation - 10,11-Epoxidation CYP3A4 ... [8]
MR002589 Carbamazepine 3-hydroxycarbamazepine Oxidation - 3-Hydroxylation CYP3A4 ... [8]
MR002590 Carbamazepine Carbamazepine N-glucuronide Conjugation - N-Glucuronidation UGT2B7 [8]
MR002584 10,11-Epoxycarbamazepine 10,11-Dihydroxycarbamazepine Unclear EHBP1L1 [8]
MR002585 10,11-Epoxycarbamazepine 9-hydroxymethyl-10-carbamaoyl acridan Unclear Unclear [11]
MR002586 3-hydroxycarbamazepine 2,3-Dihydroxycarbamazepine Unclear CYP3A4 ... [8]
MR002581 Carbamazepine 2,3-epoxide 2-hydroxycarbamazepine Unclear Unclear [8]
MR002582 2-hydroxycarbamazepine 2-hydroxyiminostilbene Unclear CYP3A4 [8]
MR002583 2-hydroxyiminostilbene Iminoquinone Unclear Unclear [8]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[7]
EH domain-binding protein 1-like protein 1 (EHBP1L1) DMEN029 Homo sapiens
EH1L1_HUMAN
1.4.1.3
[8]
Epoxide hydrolase 1 (EPHX1) DME0623 Homo sapiens
HYEP_HUMAN
3.3.2.9
[9]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[8]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[10]
⏷ Show the Full List of 10  DME(s)
References
1 Carbamazepine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34.
3 Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58.
4 Potential interaction between ritonavir and carbamazepine. Pharmacotherapy. 2000 Jul;20(7):851-4.
5 Carbamazepine pharmacokinetics are not affected by zonisamide: in vitro mechanistic study and in vivo clinical study in epileptic patients. Epilepsy Res. 2004 Nov;62(1):1-11.
6 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.
7 CYP3A4 and CYP3A7-mediated carbamazepine 10,11-epoxidation are activated by differential endogenous steroids. Drug Metab Dispos. 2003 Apr;31(4):432-8.
8 Carbamazepine and its metabolites in human perfused placenta and in maternal and cord blood Epilepsia. 1995 Mar;36(3):241-8. doi: 10.1111/j.1528-1157.1995.tb00991.x.
9 Haplotype structures of EPHX1 and their effects on the metabolism of carbamazepine-10,11-epoxide in Japanese epileptic patients. Eur J Clin Pharmacol. 2005 Mar;61(1):25-34.
10 Association of carbamazepine major metabolism and transport pathway gene polymorphisms and pharmacokinetics in patients with epilepsy. Pharmacogenomics. 2013 Jan;14(1):35-45.
11 PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA165817070)

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