Oxcarbazepine

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H12N2O2
Molecular Weight	252.268
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)N1C2=CC=CC=C2CC(=O)C3=CC=CC=C13

InChI

InChIKey=CTRLABGOLIVAIY-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C15H12N2O2
Molecular Weight	252.268
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://adisinsight.springer.com/drugs/800020351 | https://www.ncbi.nlm.nih.gov/pubmed/28182284 | https://www.ncbi.nlm.nih.gov/pubmed/23861647http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021014s026,021285s021lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11394728

Oxcarbazepine and its active metabolite (10,11-dihydro-10-hydroxy-carbazepine, MHD) have been effective in animal models of epilepsy that generally predict efficacy in generalized tonic-clonic seizures and partial seizures in humans. The pharmacokinetic profile of oxcarbazepine is less complicated than that of carbamazepine, with less metabolism by the cytochrome P450 system, no production of an epoxide metabolite, and lower plasma protein binding. The clinical efficacy and tolerability of oxcarbazepine have been demonstrated in trials in adults, children, and the elderly. The pharmacological activity of oxcarbazepine is primarily exerted through the 10-monohydroxy metabolite (MHD) of oxcarbazepine. The precise mechanism by which oxcarbazepine and MHD exert their antiseizure effect is unknown; however, in vitro electrophysiological studies indicate that they produce blockade of voltage-sensitive sodium channels, resulting in stabilization of hyperexcited neural membranes, inhibition of repetitive neuronal firing, and diminution of propagation of synaptic impulses. These actions are thought to be important in the prevention of seizure spread in the intact brain. In addition, increased potassium conductance and modulation of high-voltage activated calcium channels may contribute to the anticonvulsant effects of the drug.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
sodium ion transport 14 Target ID: GO:0006814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10411478 \| https://www.ncbi.nlm.nih.gov/pubmed/8039471 \| http://adisinsight.springer.com/drugs/800020351 \| https://www.ncbi.nlm.nih.gov/pubmed/7705430	Inhibitor 8504
Sodium channel alpha subunit 72 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8156978	Blocker 555		50.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bipolar disorder 34 Sources: http://adisinsight.springer.com/drugs/800020351	Primary		Phase III 665	Unknown Approved Use Unknown
Partial seizures 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021014s026,021285s021lbl.pdf	Primary		Approved 8583	TRILEPTAL Approved Use Oxcarbazepine tablets are indicated for use as monotherapy or adjunctive therapy in the treatment of partial seizures in adults and as monotherapy in the treatment of partial seizures in children aged 4 years and above with epilepsy, and as adjunctive therapy in children aged 2 years and above with partial seizures. Oxcarbazepine tablet is an antiepileptic drug indicated for: Adults: -Monotherapy or adjunctive therapy in the treatment of partial seizures Children: -Monotherapy in the treatment of partial seizures in children 4-16 years -Adjunctive therapy in the treatment of partial seizures in children 2-16 years (1) Launch Date 2000

C_max

Value	Dose	Analyte	Population
30.7 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258749/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	LICARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
77.6 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258749/	500 mg 3 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LICARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9349.83 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849797	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	LICARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fed
3537.63 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849797	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fed
7119 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00850174	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	LICARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fasted
1630.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00850174	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fasted
1.55 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26514967	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
503 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258749/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	LICARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
747 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258749/	500 mg 3 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LICARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
197864.34 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849797	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	LICARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fed
179002.4 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849797	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	LICARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fed
9679.79 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849797	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fed
9445.55 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849797	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fed
173770 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00850174	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	LICARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fasted
157372 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00850174	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	LICARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fasted
5873.1 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00850174	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fasted
5309.5 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00850174	600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: age: sex: food status: Fasted
3.76 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26514967	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
9.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258749/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	LICARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258749/	500 mg 3 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LICARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26514967	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXCARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
70% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20578208/			LICARBAZEPINE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
27% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26514967	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OXCARBAZEPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
8 mg/kg 1 times / day steady, oral Recommended Dose: 8 mg/kg, 1 times / day Route: oral Route: steady Dose: 8 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	unhealthy, 1 month -4 years Health Status: unhealthy Age Group: 1 month -4 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	Disc. AE: Convulsions, Status epilepticus... AEs leading to discontinuation/dose reduction: Convulsions (3.7%) Status epilepticus (1.2%) Ataxia (1.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf
15 g single, oral Overdose Dose: 15 g Route: oral Route: single Dose: 15 g Sources: https://pubmed.ncbi.nlm.nih.gov/19552755	unhealthy, 13 years Health Status: unhealthy Age Group: 13 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/19552755	Other AEs: Vomiting... Other AEs: Vomiting (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/19552755
2700 mg 1 times / day multiple, oral Highest studied dose Dose: 2700 mg, 1 times / day Route: oral Route: multiple Dose: 2700 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22850688	unhealthy, 19-70 years Health Status: unhealthy Age Group: 19-70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22850688	Other AEs: Dizziness, Tremor... Other AEs: Dizziness Tremor Somnolence Headache Sources: https://pubmed.ncbi.nlm.nih.gov/22850688
30600 mg single, oral Overdose Dose: 30600 mg Route: oral Route: single Dose: 30600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15327594	unhealthy, 36 years Health Status: unhealthy Age Group: 36 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15327594	Sources: https://pubmed.ncbi.nlm.nih.gov/15327594
8 mg/kg 1 times / day steady, oral Recommended Dose: 8 mg/kg, 1 times / day Route: oral Route: steady Dose: 8 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	unhealthy, 4-16 years Health Status: unhealthy Age Group: 4-16 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	Disc. AE: Somnolence, Vomiting... AEs leading to discontinuation/dose reduction: Somnolence (2.4%) Vomiting (2%) Ataxia (1.8%) Diplopia (1.3%) Dizziness (1.3%) Fatigue (1.1%) Nystagmus (1.1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf
12 mg/kg 1 times / day steady, oral Dose: 12 mg/kg, 1 times / day Route: oral Route: steady Dose: 12 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28580160	unhealthy, 6 years Health Status: unhealthy Age Group: 6 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/28580160	Disc. AE: Stevens Johnson syndrome... AEs leading to discontinuation/dose reduction: Stevens Johnson syndrome (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/28580160
300 mg 2 times / day steady, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: steady Dose: 300 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	Disc. AE: Hyponatremia... AEs leading to discontinuation/dose reduction: Hyponatremia (2.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf
300 mg 2 times / day steady, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: steady Dose: 300 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf	Disc. AE: Dizziness, Diplopia... AEs leading to discontinuation/dose reduction: Dizziness (6.4%) Diplopia (5.9%) Ataxia (5.2%) Vomiting (5.1%) Nausea (4.9%) Somnolence (3.8%) Headache (2.9%) Fatigue (2.1%) Abnormal vision (2.1%) Tremor (1.8%) Abnormal gait (1.7%) Rash (1.4%) Hyponatremia (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/077802s000lbl.pdf
500 mg 2 times / day multiple, oral Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18258749/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18258749/	Sources: https://pubmed.ncbi.nlm.nih.gov/18258749/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP3 246 MRP4 290 CYP1A2 2153 CYP2A6 879 CYP2E1 1060 CYP3A4/5 296 CYP4A9/11 35 CYP2C19 2057 OATP1B1 1079 OATP1B3 961 BSEP 550 MRP2 499 ALDH1 41	AKR1C1 22 AKR1C2 12 AKR1C3 13 AKR1C4 7 P-gp 2052 UGT1A9 423 UGT2B7 456 UGT1A4 399	CYP3A4/5 133 UGT 32

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
ALDH1 41	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwNjgifX0%3D	inconclusive [Activation 39.8107 uM]
UGT 70	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=19 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021014s043lbl.pdf#page=18 Page: (Pharm) 19, (Label) 18	likely
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	no [Ki 1150 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	no [Ki >1350 uM]	MHD 2
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	no [Ki >1350 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	no [Ki >1350 uM]	MHD 2
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	no [Ki >1350 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	no [Ki >1350 uM]	MHD 2
CYP4A9/11 35	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	no [Ki >1350 uM]
CYP4A9/11 35	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	no [Ki >1350 uM]	MHD 2
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	no [Ki >1800 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	no [Ki >1800 uM]	MHD 2
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	no [Ki >900 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	no [Ki >900 uM]	MHD 2
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	weak [Ki 270 uM]
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	weak [Ki 647 uM]	MHD 2
UGT 70	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=19 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021014s043lbl.pdf#page=18 Page: (Pharm) 19, (Label) 18	weak	MHD 2
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=154 Page: (Pharm) 18-19, (PMDA_I100) 154	yes [Ki 228 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=18 \| https://www.pmda.go.jp/drugs/2016/P20160602001/620095000_22800AMX00424_I100_1.pdf#page=155 Page: (Pharm) 18-19, (PMDA_I100) 155	yes [Ki 88 uM]	MHD 2
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021014s043lbl.pdf#page=18 Page: (Label) 18	yes	MHD 2
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=19 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021014s043lbl.pdf#page=18 Page: (Pharm) 19, (Label) 18	yes		yes (co-administration study) Comment: Coadministration of OXCARBAZEPINE decreased the AUC for Felodipine and Ethinylestradiol (both CYP3A4 substrate) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/21-014_TRILEPTAL_pharmr_P1.pdf#page=19 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021014s043lbl.pdf#page=18 Page: (Pharm) 19, (Label) 18

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	major	MHD 2
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	major	MHD 2
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	minor	MHD 2
AKR1C1 22	substrate 4014 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 24.3 uM]
AKR1C4 7	substrate 4014 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 2583 uM]
AKR1C2 12	substrate 4014 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 59 uM]
AKR1C3 13	substrate 4014 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 90 uM]
P-gp 2052	substrate 4014 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/28528287/	yes		yes (co-administration study) Comment: Co-administration of verapamil (P-gp inhibitor) resulted in a modest increase of the apparent bioavailability of oxcarbazepine by 12% (10-28), but did not affect parent or metabolite clearances. Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/28528287/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7824	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7824
ChemicalBook	CB9238172	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9238172
eMolecules	592941	https://www.emolecules.com/cgi-bin/more?vid=592941
MolPort	MolPort-001-685-316	https://www.molport.com/shop/molecule-link/MolPort-001-685-316
Selleck Chemicals	Oxcarbazepine	http://www.selleckchem.com/products/Oxcarbazepine.html
ZINC	ZINC000000004724	http://zinc15.docking.org/substances/ZINC000000004724

PubMed

Title	Date	PubMed
Oxcarbazepine in the treatment of epilepsy.	2001 Aug	11718497
Removal of 10-hydroxycarbazepine by plasmapheresis.	2001 Aug	11477319
Clinical pharmacology and therapeutic use of the new antiepileptic drugs.	2001 Dec	11860529
Oxcarbazepine: new preparation. An alternative to carbamazepine in partial epilepsy.	2001 Dec	11824439
[Ad hoc change from carbamazepine to oxcarbazepine--effectiveness and tolerance. A retrospective analysis].	2001 Dec	11789435
Thyroid function in men taking carbamazepine, oxcarbazepine, or valproate for epilepsy.	2001 Jul	11488894
Monotherapy trials: presurgical studies.	2001 May	11461799
Change in oxcarbazepine (Trileptal) formulation is associated with more side effects and higher blood concentrations.	2001 Nov	11688497
Review of treatment options for refractory epilepsy: new medications and vagal nerve stimulation.	2001 Nov	11673017
Anticonvulsants in the treatment of mood disorders: assessing current and future roles.	2001 Oct	11825302
Infantile spasms: diagnosis and assessment of treatment response by video-EEG.	2001 Oct	11665822
Plasma concentration of topiramate correlates with cerebrospinal fluid concentration.	2001 Oct	11591899
What's new: newly approved drugs for children.	2001 Oct	11581490
Open pilot study on oxcarbazepine for the treatment of notalgia paresthetica.	2001 Oct	11568762
Development of a high throughput 96-well plate sample preparation method for the determination of trileptal (oxcarbazepine) and its metabolites in human plasma.	2001 Oct 5	11589463
Recommendations on the clinical use of oxcarbazepine in the treatment of epilepsy: a consensus view.	2001 Sep	11551237
Levetiracetam, oxcarbazepine, remacemide and zonisamide for drug resistant localization-related epilepsy: a systematic review.	2001 Sep	11518627
Oxcarbazepine (Trileptal) as monotherapy in patients with partial seizures.	2001 Sep 11	11552018
Clinical pharmacodynamics and pharmacokinetics of antimanic and mood-stabilizing medications.	2002	11913673
The 'number needed to treat' with levetiracetam (LEV): comparison with the other new antiepileptic drugs (AEDs).	2002 Apr	12185762
Oxcarbazepine-induced syndrome of inappropriate secretion of antidiuretic hormone.	2002 Aug	12197457
Women with PTSD: the psychodynamic aspects of psychopharmacologic and "hands-on" psychiatric management.	2002 Fall	12389515
Oxcarbazepine treatment of refractory bipolar disorder: a retrospective chart review.	2002 Feb	12047498
New antiepileptic drugs: review on drug interactions.	2002 Feb	11805729
Enzyme-inducing antiepileptic drugs in pregnancy and the risk of bleeding in the neonate.	2002 Feb 26	11865131
Using the new antiepilepsy drugs in children.	2002 Jan	11918465
Newer therapies in the drug treatment of epilepsy.	2002 Jan	11816240
Validated assay for quantification of oxcarbazepine and its active dihydro metabolite 10-hydroxycarbazepine in plasma by atmospheric pressure chemical ionization liquid chromatography/mass spectrometry.	2002 Jul	12125001
Gateways to clinical trials.	2002 Jul-Aug	12224444
Gateways to Clinical Trials. June 2002.	2002 Jun	12168506
Some common issues in the use of antiepileptic drugs.	2002 Mar	12170391
Oxcarbazepine and hyponatremia.	2002 Mar 1	11887415
Effects of oxcarbazepine on sodium concentration and water handling.	2002 May	12112108
Oxcarbazepine final market image tablet formulation bioequivalence study after single administration and at steady state in healthy subjects.	2002 Nov	12698990
Oxcarbazepine for mood disorders.	2002 Oct	12359694
[Monitoring serum levels of new antiepileptics].	2002 Sep	12373664
[Characteristics and indications of oxcarbazepine].	2002 Sep	12373662
Octakis-6-sulfato-gamma-cyclodextrin as additive for capillary electrokinetic chromatography of dibenzoazepines: carbamazepine, oxcarbamazepine and their metabolites.	2002 Sep	12207311
Use of anticonvulsants for treatment of neuropathic pain.	2002 Sep 10	12221151
Antiepileptic drug use during the first 12 months of vagus nerve stimulation therapy: a registry study.	2002 Sep 24	12270967
Pharmacokinetics of mood stabilizers and new anticonvulsants.	2002 Winter	12397847
Assessment of the bioequivalence of two oxcarbazepine oral suspensions versus a film-coated tablet in healthy subjects.	2003 Jul	12875346
Overview of the clinical pharmacokinetics of oxcarbazepine.	2004	17516704
Simultaneous liquid chromatographic determination of lamotrigine, oxcarbazepine monohydroxy derivative and felbamate in plasma of patients with epilepsy.	2005 Dec 15	16182617
Drug monitoring and toxicology: a procedure for the monitoring of oxcarbazepine metabolite by HPLC-UV.	2006 Jan	16599412
A novel enantioselective microassay for the high-performance liquid chromatography determination of oxcarbazepine and its active metabolite monohydroxycarbazepine in human plasma.	2007 Jun	17529889
Stereoselective disposition of S- and R-licarbazepine in mice.	2008 Jun	18306292
Pharmacokinetics of licarbazepine in healthy volunteers: single and multiple oral doses and effect of food.	2008 May	18258749
Binding of licarbazepine enantiomers to mouse and human plasma proteins.	2010 Jul	20578208
Development and validation of an HPLC-UV method for the simultaneous quantification of carbamazepine, oxcarbazepine, eslicarbazepine acetate and their main metabolites in human plasma.	2010 Jun	20401721

Patents

Sample Use Guides

In Vivo Use Guide

Bipolar I Disorder: 750- 2000 mg/day

Route of Administration: Oral

In Vitro Use Guide

Free and bound fractions of S-licarbazepine (S-Lic) and R-licarbazepine (R-Lic) were separated by ultrafiltration after previous in vitro incubation of spiked plasma samples and protein solutions with each enantiomer at 10, 25 and 50 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:31 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:31 GMT 2025`
Record UNII	VZI5B1W380
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Oxcarbazepine

Official Name

English

OXTELLAR XR

Preferred Name

English

Oxcarbazepine [VANDF]

Common Name

English

Trileptal

Common Name

English

Oxcarbazepine [INN]

Common Name

English

Oxcarbamazepine

Common Name

English

Oxcarbazepine [HSDB]

Common Name

English

Oxcarbazepine [USP MONOGRAPH]

Common Name

English

KIN-493

Code

English

Oxcarbazepine [USAN]

Common Name

English

Oxcarbazepine [MI]

Common Name

English

Oxcarbazepine [JAN]

Common Name

English

GP-47680

Code

English

Oxcarbazepine [WHO-DD]

Common Name

English

NSC-758693

Code

English

Oxcarbazepine [EP MONOGRAPH]

Common Name

English

SPN-804

Code

English

10,11-Dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide

Systematic Name

English

Oxcarbazepine [ORANGE BOOK]

Common Name

English

Oxcarbazepine [USP-RS]

Common Name

English

Oxcarbazepine [MART.]

Common Name

English

5H-Dibenz[b,f]azepine-5-carboxamide, 10,11-dihydro-10-oxo-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C264