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 8297
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8156978	Blocker 537		50.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bipolar disorder 34 Sources: http://adisinsight.springer.com/drugs/800020351	Primary		Phase III 656	Unknown Approved Use Unknown
Partial seizures 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021014s026,021285s021lbl.pdf	Primary		Approved 8429	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
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 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP3 157 MRP4 204 CYP1A2 1524 CYP2A6 707 CYP2E1 882 CYP3A4/5 278 CYP4A9/11 37 CYP2C19 1478 OATP1B1 788 OATP1B3 706 BSEP 402 MRP2 383 ALDH1 40	AKR1C1 19 AKR1C2 9 AKR1C3 13 AKR1C4 6 P-gp 1537 UGT1A9 380 UGT2B7 389 UGT1A4 347	CYP3A4/5 124 UGT 29

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
ALDH1 40	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwNjgifX0%3D	inconclusive [Activation 39.8107 uM]
UGT 59	inducer 1573 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 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 1692	inhibitor 3277 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 1692	inhibitor 3277 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 739	inhibitor 3277 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 739	inhibitor 3277 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 1819	inhibitor 3277 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 1819	inhibitor 3277 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 3277 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 3277 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 1891	inhibitor 3277 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 1891	inhibitor 3277 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 970	inhibitor 3277 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 970	inhibitor 3277 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
CYP3A4/5 335	inhibitor 3277 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]
CYP3A4/5 335	inhibitor 3277 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 59	inducer 1573 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 1553	inhibitor 3277 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 1553	inhibitor 3277 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
CYP3A4/5 335	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021014s043lbl.pdf#page=18 Page: (Label) 18	yes	MHD 2
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
CYP3A4/5 335	inducer 1573 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 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	major	MHD 2
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	major	MHD 2
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/33793880/	minor	MHD 2
AKR1C1 19	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 24.3 uM]
AKR1C4 6	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 2583 uM]
AKR1C2 9	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 59 uM]
AKR1C3 13	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00776 \| https://pubmed.ncbi.nlm.nih.gov/25063510/	yes [Km 90 uM]
P-gp 1537	substrate 3367 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
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.	2001	11570976
Oxcarbazepine: an update of its efficacy in the management of epilepsy.	2001	11460891
Behavioural effects of the new anticonvulsants.	2001	11444724
Second generation anticonvulsant medications: their use in children.	2001 Apr	11885112
[Pharmacotherapy for neuropathic pain caused by injury to the afferent nerve fibers].	2001 Apr 28	11370425
Oxcarbazepine in the treatment of epilepsy.	2001 Aug	11718497
Newer antiepileptic drugs: advantages and disadvantages.	2001 Aug	11504596
Oxcarbazepine: new preparation. An alternative to carbamazepine in partial epilepsy.	2001 Dec	11824439
Progress report on new antiepileptic drugs: a summary of the Fifth Eilat Conference (EILAT V).	2001 Jan	11137386
Antiepileptic drug utilization: a Danish prescription database analysis.	2001 Jul	11442436
The regulation of serum sodium after replacing carbamazepine with oxcarbazepine.	2001 Jun	11422328
Suppressive effects of oxcarbazepine on tooth pulp-evoked potentials recorded at the trigeminal spinal tract nucleus in cats.	2001 Mar	11207671
Clinical recommendations for oxcarbazepine.	2001 Mar	11421225
Synthesis, anticonvulsant properties and pharmacokinetic profile of novel 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide derivatives.	2001 Mar	11337101
Possible oxcarbazepine interaction with cyclosporine serum levels: a single case study.	2001 Mar-Apr	11307049
Monotherapy trials: presurgical studies.	2001 May	11461799
Transplacental passage of oxcarbazepine and its metabolites in vivo.	2001 Nov	11879354
Oxcarbazepine in affective and schizoaffective disorders.	2001 Nov	11778145
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
[Oxcarbazepine].	2001 Oct	11738014
Plasma concentration of topiramate correlates with cerebrospinal fluid concentration.	2001 Oct	11591899
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
Interactions between antiepileptic drugs and hormonal contraception.	2002	11945109
Gabapentin: new indication. Little impact on partial epilepsy in children between 3 and 12.	2002 Apr	11987312
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
Marketed new antiepileptic drugs: are they better than old-generation agents?	2002 Feb	11805726
Three new drugs for epilepsy: levetiracetam, oxcarbazepine, and zonisamide.	2002 Jan	11918464
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. June 2002.	2002 Jun	12168506
Oxcarbazepine for epilepsy--a useful new choice?	2002 Jun	12143266
Oxcarbazepine and hyponatremia.	2002 Mar 1	11887415
Effects of oxcarbazepine on sodium concentration and water handling.	2002 May	12112108
Oxcarbazepine for mood disorders.	2002 Oct	12359694
Octakis-6-sulfato-gamma-cyclodextrin as additive for capillary electrokinetic chromatography of dibenzoazepines: carbamazepine, oxcarbamazepine and their metabolites.	2002 Sep	12207311
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
Stereoselective disposition of S- and R-licarbazepine in mice.	2008 Jun	18306292
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 `Fri Dec 15 15:55:36 GMT 2023` Edited by `admin` on `Fri Dec 15 15:55:36 GMT 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