Compound: OXCARBAZEPINE
SMILES: O=C1c2c(N(C(=O)N)c3c(C1)cccc3)cccc2
InChIKey: CTRLABGOLIVAIY-UHFFFAOYSA-N
Synonyms: 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
Theoretical properties:
molecular_formula: C15H12N2O2
molecular_weight: 252.27 g/mol
exact_mass: 252.089877630 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 19
topological_polar_surface_area: 63.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from ethanol
color: Crystals from ethanol
melting_point: 215-216 °C
solubility: Slightly soluble in chloroform, dichloromethane, acetone, and methanol and practically insoluble in ethanol, ether, and water.
Descriptions:
pubchem: Oxcarbazepine is a dibenzoazepine derivative, having a carbamoyl group at the ring nitrogen, substituted with an oxo group at C-4 of the azepeine ring which is also hydrogenated at C-4 and C-5. It is a anticholinergic anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy. It has a role as an anticonvulsant and a drug allergen. It is a cyclic ketone and a dibenzoazepine. It contains a carbamoyl group.
chebi: A dibenzoazepine derivative, having a carbamoyl group at the ring nitrogen, substituted with an oxo group at C-4 of the azepeine ring which is also hydrogenated at C-4 and C-5. It is a anticholinergic anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy.
chembl: OXCARBAZEPINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Oxcarbazepine, sold under the brand name Trileptal among others, is a medication used to treat epilepsy. For epilepsy it is used for both focal seizures and generalized seizures. It has been used both alone and as add-on therapy in people with bipolar disorder who have had no success with other treatments. It is taken by mouth.
Common side effects include nausea, vomiting, dizziness, drowsiness, double vision and trouble with walking. Serious side effects may include anaphylaxis, liver problems, pancreatitis, suicide ideation, and an abnormal heart beat. While use during pregnancy may harm the baby, use may be less risky than having a seizure. Use is not recommended during breastfeeding. In those with an allergy to carbamazepine there is a 25% risk of problems with oxcarbazepine. How it works is not entirely clear.
Oxcarbazepine was patented in 1969 and came into medical use in 1990. It is available as a generic medication. In 2023, it was the 224th most commonly prescribed medication in the United States, with more than 1 million prescriptions.