LICARBAZEPINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H14N2O2
Molecular Weight	254.2839
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)N1C2=CC=CC=C2CC(O)C3=C1C=CC=C3

InChI

InChIKey=BMPDWHIDQYTSHX-UHFFFAOYSA-N

InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)

HIDE SMILES / InChI

Molecular Formula	C15H14N2O2
Molecular Weight	254.2839
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 8228
Sodium channel alpha subunit 72 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8156978	Blocker 534		50.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bipolar disorder 34 Sources: http://adisinsight.springer.com/drugs/800020351	Primary		Phase III 663	Unknown Approved Use Unknown
Partial seizures 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021014s026,021285s021lbl.pdf	Primary		Approved 8360	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 9.4780798E11

C_max

Value	Dose	Analyte	Population
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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
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
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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 (starting) 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 n = 241 Health Status: unhealthy Condition: partial seizures Age Group: 1 month -4 years Population Size: 241 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 n = 1 Health Status: unhealthy Age Group: 13 years Sex: M Population Size: 1 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 n = 71 Health Status: unhealthy Age Group: 19-70 years Sex: M+F Population Size: 71 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 n = 1 Health Status: unhealthy Age Group: 36 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15327594	Sources: https://pubmed.ncbi.nlm.nih.gov/15327594
8 mg/kg 1 times / day steady, oral (starting) 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 n = 456 Health Status: unhealthy Condition: partial seizures Age Group: 4-16 years Population Size: 456 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 (starting) 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 n = 1 Health Status: unhealthy Condition: f benign rolandic epilepsy Age Group: 6 years Sex: M Population Size: 1 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 (starting) 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 n = 1524 Health Status: unhealthy Condition: epilepsy Age Group: adult Population Size: 1524 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 (starting) 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 n = 1537 Health Status: unhealthy Condition: partial seizures Age Group: adult Population Size: 1537 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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP3 157 MRP4 203 CYP1A2 1509 CYP2A6 704 CYP2E1 876 CYP3A4/5 273 CYP4A9/11 37 CYP2C19 1463 OATP1B1 781 OATP1B3 700 BSEP 401 MRP2 367 ALDH1 40	AKR1C1 19 AKR1C2 9 AKR1C3 13 AKR1C4 6 P-gp 1527 UGT1A9 380 UGT2B7 389 UGT1A4 347	CYP3A4/5 120 UGT 29

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
ALDH1 40	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwNjgifX0%3D	inconclusive [Activation 39.8107 uM]
UGT 58	inducer 1542 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 402	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 459	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 208	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 237	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 1673	inhibitor 3240 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 1673	inhibitor 3240 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 736	inhibitor 3240 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 736	inhibitor 3240 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 1803	inhibitor 3240 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 1803	inhibitor 3240 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 37	inhibitor 3240 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 37	inhibitor 3240 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 1875	inhibitor 3240 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 1875	inhibitor 3240 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 964	inhibitor 3240 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 964	inhibitor 3240 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
CYP3A4/5 330	inhibitor 3240 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]
CYP3A4/5 330	inhibitor 3240 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 58	inducer 1542 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 1537	inhibitor 3240 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 1537	inhibitor 3240 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
CYP3A4/5 330	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021014s043lbl.pdf#page=18 Page: (Label) 18	yes	MHD 2
OATP1B1 796	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 709	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
CYP3A4/5 330	inducer 1542 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 380	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	major	MHD 2
UGT2B7 389	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	major	MHD 2
UGT1A4 347	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	minor	MHD 2
AKR1C1 19	substrate 3326 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 24.3 uM]
AKR1C4 6	substrate 3326 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 2583 uM]
AKR1C2 9	substrate 3326 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 59 uM]
AKR1C3 13	substrate 3326 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 90 uM]
P-gp 1527	substrate 3326 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
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
eMolecules	592941	https://www.emolecules.com/cgi-bin/more?vid=592941

PubMed

Title	Date	PubMed
[New antiepileptic drugs in childhood epilepsies: indications and limits].	2001	11827845
Second generation anticonvulsant medications: their use in children.	2001 Apr	11885112
Clinical pharmacology and therapeutic use of the new antiepileptic drugs.	2001 Dec	11860529
Suppressive effects of oxcarbazepine on tooth pulp-evoked potentials recorded at the trigeminal spinal tract nucleus in cats.	2001 Mar	11207671
Symptomatic trigeminal-autonomic cephalalgia evolving to trigeminal neuralgia: report of a case associated with dual pathology.	2001 Nov	11903287
Transplacental passage of oxcarbazepine and its metabolites in vivo.	2001 Nov	11879354
Anticonvulsants in the treatment of mood disorders: assessing current and future roles.	2001 Oct	11825302
Treatment of epilepsy in women of reproductive age: pharmacokinetic considerations.	2002	12102641
Interactions between antiepileptic drugs and hormonal contraception.	2002	11945109
Clinical pharmacodynamics and pharmacokinetics of antimanic and mood-stabilizing medications.	2002	11913673
Effect of antiepileptic drugs on cognitive function in individuals with epilepsy: a comparative review of newer versus older agents.	2002	11893228
Anticonvulsants: aspects of their mechanisms of action.	2002	11888234
The 'number needed to treat' with levetiracetam (LEV): comparison with the other new antiepileptic drugs (AEDs).	2002 Apr	12185762
Gabapentin: new indication. Little impact on partial epilepsy in children between 3 and 12.	2002 Apr	11987312
Oxcarbazepine and hepatic porphyria.	2002 Apr	11952779
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
Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024.	2002 Feb	11926264
Metabolism of 10,11-dihydro-10-hydroxyimino-5H-dibenz/b, f/azepine-5-carboxamide, a potent anti-epileptic drug.	2002 Feb	11868969
The promise of new antiepileptic drugs.	2002 Feb	11851635
Long-term cohort study comparing medical (oxcarbazepine) and surgical management of intractable trigeminal neuralgia.	2002 Feb	11839425
Enzyme-inducing antiepileptic drugs in pregnancy and the risk of bleeding in the neonate.	2002 Feb 26	11865131
Pediatric partial and generalized seizures.	2002 Jan	11918466
Using the new antiepilepsy drugs in children.	2002 Jan	11918465
Three new drugs for epilepsy: levetiracetam, oxcarbazepine, and zonisamide.	2002 Jan	11918464
Oxcarbazepine.	2002 Jan	11888266
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
Oxcarbazepine for epilepsy--a useful new choice?	2002 Jun	12143266
Serum concentrations of topiramate in patients with epilepsy: influence of dose, age, and comedication.	2002 Jun	12021627
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
[New antiepileptic drugs: new therapeutic options].	2002 May	11997751
LC determination of oxcarbazepine and its active metabolite in human serum.	2002 May 15	12008131
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
Progress report on new antiepileptic drugs: a summary of the Sixth Eilat Conference (EILAT VI).	2002 Sep	12350382
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
Safety, tolerability, and pharmacokinetic profile of BIA 2-093, a novel putative antiepileptic, in a rising multiple-dose study in young healthy humans.	2004 Aug	15286095
Simultaneous liquid chromatographic determination of lamotrigine, oxcarbazepine monohydroxy derivative and felbamate in plasma of patients with epilepsy.	2005 Dec 15	16182617
Eyeblink conditioning anomalies in bipolar disorder suggest cerebellar dysfunction.	2009 Feb	19133963
Binding of licarbazepine enantiomers to mouse and human plasma proteins.	2010 Jul	20578208

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 `Wed Jul 05 23:23:55 UTC 2023` Edited by `admin` on `Wed Jul 05 23:23:55 UTC 2023`
Record UNII	XFX1A5KJ3V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LICARBAZEPINE

Official Name

English

licarbazepine [INN]

Common Name

English

10,11-DIHYDRO-10-HYDROXY-5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE

Systematic Name

English

Licarbazepine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C264