Oxcarbazepine

An orally administered antiepileptic drug used as monotherapy or adjunctive therapy for focal-onset seizures. Oxcarbazepine is rapidly converted to its pharmacologically active monohydroxy metabolite (MHD), which stabilizes hyperexcited neuronal membranes by inhibiting voltage-gated sodium channels and reducing repetitive neuronal firing. It is structurally related to carbamazepine but has a different metabolic profile and a lower propensity for certain drug interactions. Hyponatremia is an important potential adverse effect

CAS Number: 28721-07-5

Molecular Mass: 252.27 g/mol

Formula: C₁₅H₁₂N₂O₂

Smiles: NC(=O)N1c2ccccc2CC(=O)c2ccccc21

Synonymes:

Oxcarbazepine, OXCARBAZEPINE, 28721-07-5, Trileptal, Oxcarbamazepine, Oxcarbazepina, 10-Oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide, Oxcarbazepinum, GP-47680, Oxtellar XR, KIN-493, 5H-Dibenz[b,f]azepine-5-carboxamide, 10,11-dihydro-10-oxo-, 5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide, 10,11-Dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide, SPN-804, 10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carboxamide, DTXSID0045703, NSC-758693, OCBZ, CHEBI:7824, VZI5B1W380, 5H-Dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-10-oxo-, 9-oxo-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide, DTXCID8025703, OX-CBZ, 5-oxo-6H-benzo(b)(1)benzazepine-11-carboxamide, 10-oxo-10,11-dihydro-5H-dibenzo(b,f)azepine-5-carboxamide, 9-oxo-2-azatricyclo(9.4.0.0^(3,8))pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide, RefChem:57861, N03AF02, 9-oxo-2-azatricyclo(9.4.0.03,8)pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide, 249-188-8, GP 47680, MFCD00865307, MLS000084586, CHEMBL1068, SMR000048684, Timox, s1391, NCGC00065934-02, Oxcarbazepine [INN], M06310, Oxcarbazepinum [INN-Latin], Oxcarbazepina [INN-Spanish], Oxcarbazepime, Epilexter, Epliga, Trileptal (TN), CAS-28721-07-5, SR-01000612612, EINECS 249-188-8, UNII-VZI5B1W380, Aurene, Oxcarb, , HSDB 7524, Oxcarbazepine CRS, Oxtellar (TN), Oxcarbazepine [USAN:USP:INN:BAN], Spectrum_001675, Opera_ID_818, Oxcarbazepine (Standard), regid866068, Spectrum2_000483, Spectrum3_001669, Spectrum4_000634, Spectrum5_001869, O0363, OXCARBAZEPINE [MI], Epitope ID:423615, OXCARBAZEPINE [JAN], OXCARBAZEPINE [HSDB], OXCARBAZEPINE [USAN], SCHEMBL35129, BSPBio_003457, KBioGR_001248, KBioSS_002155, OXCARBAZEPINE [VANDF], cid_34312, MLS000759520, MLS001201742, MLS001424025, MLS006011855, BIDD:GT0078, OXCARBAZEPINE [MART.], SPECTRUM1504243, SPBio_000345, OXCARBAZEPINE [USP-RS], OXCARBAZEPINE [WHO-DD], GTPL7254, orb1310614, orb3025230, Oxcarbazepine (JAN/USP/INN), SCHEMBL29359799, SCHEMBL29433241, BDBM34179, HY-B0114R, KBio2_002155, KBio2_004723, KBio2_007291, KBio3_002677, Oxcarbazepine - Bio-X trade mark, Oxcarbazepine, analytical standard, 10,11-Dihydro-10-oxo-5H-dibenzo[b,f]azepine-5-carboxamide, GLXC-07167, HMS1922H17, HMS2051O04, HMS2090F13, HMS2093E10, HMS2231B12, HMS3369J22, HMS3393O04, HMS3657O11, HMS3713I10, HMS3884K13, HMS5079F19, Pharmakon1600-01504243, OXCARBAZEPINE [ORANGE BOOK], HY-B0114, MSK10264, OXCARBAZEPINE [EP MONOGRAPH], Tox21_110983, CCG-39509, EBC-03777, NSC758693, OXCARBAZEPINE [USP MONOGRAPH], STK594696, AKOS005516529, Oxcarbazepine, 1mg/ml in Acetonitrile, Tox21_110983_1, AC-3483, CS-1869, DB00776, FO26622, KS-5197, NC00088, NSC 758693, Oxcarbazepine, >=98% (HPLC), solid, NCGC00065934-03, NCGC00065934-04, NCGC00065934-05, NCGC00065934-06, BO164187, SY052973, SBI-0206772.P001, GP-47-680, NS00010016, SW197468-3, T0440, C07492, D00533, EN300-123538, AB00393017-12, AB00393017-14, AB00393017_15, AB00393017_16, Q176301, SR-01000612612-4, SR-01000612612-6, BRD-K04196797-001-12-9, BRD-K04196797-001-23-6, BRD-K04196797-001-24-4, BRD-K04196797-001-25-1, Z1551967555, 10-oxo-10,11-dihydro-5H-dibenz(b,f)azepin-5-carboxamide, 5-carbamoyl-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine, 10,11-Dihydro-10-oxo-5H-dibenz[b,f]azepin-5-carbonsaeureamid, 10-Oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide #, Oxcarbazepine Working Standard (Secondary Reference Standard), Oxcarbazepine, European Pharmacopoeia (EP) Reference Standard, Oxcarbazepine, United States Pharmacopeia (USP) Reference Standard, 9-oxo-2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide, Oxcarbazepine, Pharmaceutical Secondary Standard, Certified Reference Material

Bioactivity: Anticonvulsant; voltage-gated sodium channel blocker (primarily via its active monohydroxy metabolite

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	288.15	-	0.6951	[96]
1-Butanol	293.15	-	0.8517	[96]
1-Butanol	298.15	-	0.9739	[96]
1-Butanol	303.15	-	1.308	[96]
1-Butanol	308.15	-	1.677	[96]
1-Propanol	288.15	-	0.8307	[96]
1-Propanol	293.15	-	1.016	[96]
1-Propanol	298.15	-	1.202	[96]
1-Propanol	303.15	-	1.587	[96]
1-Propanol	308.15	-	2.048	[96]
Acetone	288.15	-	3.636	[96]
Acetone	293.15	-	4.12	[96]
Acetone	298.15	-	4.574	[96]
Acetone	303.15	-	5.219	[96]
Acetone	308.15	-	6.125	[96]
Acetonitrile	288.15	-	3.105	[96]
Acetonitrile	293.15	-	3.613	[96]
Acetonitrile	298.15	-	4.008	[96]
Acetonitrile	303.15	-	4.887	[96]
Acetonitrile	308.15	-	5.749	[96]
Diethylene Glycol Monoethyl Ether	288.15	-	7.831	[97]
Diethylene Glycol Monoethyl Ether	293.15	-	8.151	[97]
Diethylene Glycol Monoethyl Ether	298.15	-	8.468	[97]
Diethylene Glycol Monoethyl Ether	303.15	-	8.782	[97]
Diethylene Glycol Monoethyl Ether	308.15	-	9.112	[97]
Dimethyl sulfoxide	288.15	-	115.0	[97]
Dimethyl sulfoxide	293.15	-	124.7	[97]
Dimethyl sulfoxide	298.15	-	134.8	[97]
Dimethyl sulfoxide	303.15	-	93.62	[97]
Dimethyl sulfoxide	308.15	-	102.8	[97]
Dimethylacetamide	288.15	-	71.94	[97]
Dimethylacetamide	293.15	-	52.49	[97]
Dimethylacetamide	298.15	-	56.74	[97]
Dimethylacetamide	303.15	-	61.25	[97]
Dimethylacetamide	308.15	-	65.73	[97]
Dimethylformamide	288.15	-	67.85	[97]
Dimethylformamide	293.15	-	70.92	[97]
Dimethylformamide	298.15	-	57.72	[97]
Dimethylformamide	303.15	-	60.41	[97]
Dimethylformamide	308.15	-	63.46	[97]
Ethanol	288.15	-	1.186	[96]
Ethanol	293.15	-	1.393	[96]
Ethanol	298.15	-	1.648	[96]
Ethanol	303.15	-	2.088	[96]
Ethanol	308.15	-	2.625	[96]
Isopropanol	288.15	-	0.5008	[96]
Isopropanol	293.15	-	0.6168	[96]
Isopropanol	298.15	-	0.7116	[96]
Isopropanol	303.15	-	0.9755	[96]
Isopropanol	308.15	-	1.34	[96]
Methanol	288.15	-	3.347	[96]
Methanol	293.15	-	3.857	[96]
Methanol	298.15	-	4.702	[96]
Methanol	303.15	-	5.587	[96]
Methanol	308.15	-	6.797	[96]
N-Methyl-2-pyrrolidone	288.15	-	94.62	[97]
N-Methyl-2-pyrrolidone	293.15	-	97.64	[97]
N-Methyl-2-pyrrolidone	298.15	-	100.3	[97]
N-Methyl-2-pyrrolidone	303.15	-	103.0	[97]
N-Methyl-2-pyrrolidone	308.15	-	89.93	[97]
Tetrahydrofuran	288.15	-	6.389	[96]
Tetrahydrofuran	293.15	-	6.752	[96]
Tetrahydrofuran	298.15	-	7.455	[96]
Tetrahydrofuran	303.15	-	8.179	[96]
Tetrahydrofuran	308.15	-	9.414	[96]
Water	288.15	-	0.07583	[97]
Water	293.15	-	0.08177	[97]
Water	298.15	-	0.088	[97]
Water	303.15	-	0.09397	[97]
Water	308.15	-	0.1002	[97]

Molecule 3D descriptors

Descriptor	Value
PMI1	986.0099
PMI2	1327.6153
PMI3	1844.7547
NPR1	0.5345
NPR2	0.7197
RadiusOfGyration	2.8709
InertialShapeFactor	0.0007
Eccentricity	0.8452
Asphericity	0.1297
SpherocityIndex	0.4194
PBF	1.0429