Compound: carbamazepine
SMILES: O=C(N1c2c(C=Cc3c1cccc3)cccc2)N
InChIKey: FFGPTBGBLSHEPO-UHFFFAOYSA-N
Synonyms: carbamazepine, 298-46-4, Tegretol, 5H-Dibenz[b,f]azepine-5-carboxamide, Finlepsin, Tegretal, Biston, Carbamazepen, Equetro, Telesmin, Carbazepine, Timonil, Carbamezepine, Karbamazepin, Carbatrol, Neurotol, Stazepine, Epitol, Carbamazepin, Tegretol-Xr, Teril, Geigy 32883, Carbamazepina, Carbamazepinum, Carnexiv, Sirtal, benzo[b][1]benzazepine-11-carboxamide, 5-Carbamyl-5H-dibenzo(b,f)azepine, 5-Carbamoyl-5H-dibenzo(b,f)azepine, G-32883, 5H-Dibenz(b,f)azepine-5-carboxamide, Karbelex, Neurotop, Carbamazepine Anhydrous, 5-Carbamoyl-5H-dibenz(b,f)azepine, G 32883, 5-Carbamoyl-5H-dibenz[b,f]azepine, Carbamazepine extended release, NSC-169864, CHEBI:3387, DTXSID4022731, NSC169864, 33CM23913M, DTXCID902731, 5-20-08-00247 (Beilstein Handbook Reference), Tegretol XR, benzo(b)(1)benzazepine-11-carboxamide, 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide, Epimaz, Carbagen sr, Epimaz ret, Sirtal ret, Tegretol chewtab, Teril ret, Arbil mr, Carbamazepine ER, 2-azatricyclo(9.4.0.0^(3,8))pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide, Timonil 200 ret, Timonil 400 ret, RefChem:5646, Tegretol prolonged release, N03AF01, 5H-Dibenzo(b,f)azepin-5-carboxamide, 2-azatricyclo(9.4.0.03,8)pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide, 206-062-7, Carbamat, 5H-Dibenzo[b,f]azepine-5-carboxamide, Lexin, Amizepin, Bipotrol, Calepsin, MFCD00005073, Trimonil, NSC 169864, CHEMBL108, 5-Carbamyldibenzo(b,f)azepine, MLS000069652, 5-Carbamoyldibenzo(b,f)azepine, CBZ, Stazepin, dibenzo[b,f]azepine-5-carboxamide, s1693, NCGC00015234-11, CAS-298-46-4, SMR000058201, 5H-dibenzo[b,f]azepine-5-carboxamide;Oxcarbazepine IMpurity A, Carbelan, Tegretol Cr, Carbamazepinum [INN-Latin], Carbamazepina [INN-Spanish], SMR001227191, HSDB 3019, SR-01000000229, Carbatrol extended-release, EINECS 206-062-7, BRN 1246090, Carbmazepine, Neurotop retard, Carbamazepine?, Carbagamma;, Neurotop;, Tegretol;, Atretol;, Carbium;, Prozine;, Timonil;, Carbamazepine RS, Epimaz;, Epitol;, Sirtal;, UNII-33CM23913M, Carba;, Teril;, Carbamazepine CRS, Tegretol (TN), N6W, Prestwick_104, Equetro (TN), Carbamazepine, powder, Opera_ID_72, Spectrum_000096, Carbamazepine [USAN:USP:INN:BAN:JAN], Carbamazepine (Standard), Prestwick0_000052, Prestwick1_000052, Prestwick2_000052, Prestwick3_000052, Spectrum2_000125, Spectrum3_000325, Spectrum4_000262, Spectrum5_000936, Carbamazepine (Carbatrol), Lopac-C-4024, ChemDiv1_018966, CARBAMAZEPINE [MI], CBChromo1_000350, Epitope ID:174842, Iminostilbene-N-carboxamide, CARBAMAZEPINE [INN], CARBAMAZEPINE [JAN], CARBAMAZEPINE [HSDB], CARBAMAZEPINE [USAN], Lopac0_000292, Oprea1_790775, SCHEMBL21639, BSPBio_000203, BSPBio_001929, CARBAMAZEPINE [VANDF], KBioGR_000724, KBioSS_000516, MLS001055475, MLS001074172, MLS002548877, BIDD:GT0479, CARBAMAZEPINE [MART.], DivK1c_000388, DivK1c_003750, SPECTRUM1500159, SPBio_000170, SPBio_002124, CARBAMAZEPINE [USP-RS], CARBAMAZEPINE [WHO-DD], CARBAMAZEPINE [WHO-IP], BPBio1_000225, GTPL5339, orb1310147, orb3139395, SCHEMBL29360181, SCHEMBL29433237, HMS501D10, HMS640O02, HY-B0246R, KBio1_000388, KBio2_000516, KBio2_003084, KBio2_005652, KBio3_001149, WLN: T C676 BNJ BVZ, Carbamazepine (JP18/USP/INN), CBZ;NSC 169864, SPD-417, Carbamazepine - Bio-X trade mark, Carbamazepine, analytical standard, NINDS_000388, Carbamazepine, 1mg/ml in Methanol, GLXC-06091, HMS1568K05, HMS1920I17, HMS2090M07, HMS2091O19, HMS2095K05, HMS2233G16, HMS3039K09, HMS3259B21, HMS3260L06, HMS3372J13, HMS3657G03, HMS3712K05, HMS3747E03, HMS5079B14, HMS6018K08, Pharmakon1600-01500159, CARBAMAZEPINE [ORANGE BOOK], HY-B0246, MSK10039, PXB90221, 5-Carbomoyl-5H-dibenzo(b,f)azepine, CARBAMAZEPINE [EP MONOGRAPH], CARBAMAZEPINE [USP IMPURITY], Tox21_110104, Tox21_202273, Tox21_300195, Tox21_500292, AC2074, BDBM50003659, CARBAMAZEPINE [USP MONOGRAPH], CCG-38931, EBC-11073, NSC755920, STK177357, STL453548, 5H-Dibenz[b,f]azepine-5-carboxamine, Carbamazepine 1.0 mg/ml in Methanol, CARBAMAZEPINUM [WHO-IP LATIN], AKOS003235644, AKOS025397243, Tox21_110104_1, AC-9538, DB00564, KS-5146, LP00292, NC00679, NSC-755920, SDCCGSBI-0050280.P005, CDS1_002710, IDI1_000388, 5H-Dibenzo[b,f]azepine-5-carboxamide #, NCGC00015234-01, NCGC00015234-02, NCGC00015234-03, NCGC00015234-04, NCGC00015234-05, NCGC00015234-06, NCGC00015234-07, NCGC00015234-08, NCGC00015234-09, NCGC00015234-10, NCGC00015234-12, NCGC00015234-13, NCGC00015234-14, NCGC00015234-15, NCGC00015234-16, NCGC00015234-18, NCGC00015234-19, NCGC00015234-33, NCGC00023877-03, NCGC00023877-04, NCGC00023877-05, NCGC00023877-06, NCGC00023877-07, NCGC00023877-08, NCGC00253982-01, NCGC00259822-01, NCGC00260977-01, BC166161, ST075773, SY002823, Carbamazepine; Oxcarbazepine EP Impurity A, SBI-0050280.P004, 5H-dibenzo[b,f]azepine-5-carboximidic acid, DB-047659, Dibenzo[b,f]azepine-5-carboxylic acid amide, EU-0100292, NS00000207, Oxcarbazepine EP Impurity A (Carbamazepine), SW220141-1, T0943, EN300-21678, OXCARBAZEPINE IMPURITY A [EP IMPURITY], BIM-0050280.0001, C 4024, C06868, Carbamazepine, meets USP testing specifications, D00252, 5H-Dibenz(b,f)azepine-5-carboxamide maleic acid, 5H-Dibenz(b,f)azepine-5-carboxamide oxalic acid, AB00051931-17, AB00051931-18, AB00051931_19, AB00051931_20, F242225, Q410412, carbamazepine host structure with maleic acid removed, carbamazepine host structure with oxalic acid removed, SR-01000000229-2, SR-01000000229-4, SR-01000000229-7, 5H-Dibenz(b,f)azepine-5-carboxamide DL-tartaric acid, BRD-K71799949-001-06-7, BRD-K71799949-001-35-6, BRD-K71799949-001-36-4, F0348-2551, Z104508594, carbamazepine host structure with DL-tartaric acid removed, Dibenzo[b,f]azepine-5-carboxylic acid amide(Carbamazepine), carbamazepine host structure with 4-hydroxybenzoic acid removed, Carbamazepine, British Pharmacopoeia (BP) Reference Standard, Carbamazepine, European Pharmacopoeia (EP) Reference Standard, Carbamazepine, United States Pharmacopeia (USP) Reference Standard, 2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide, Carbamazepine, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C15H12N2O
molecular_weight: 236.27 g/mol
exact_mass: 236.094963011 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 0
heavy_atom_count: 18
topological_polar_surface_area: 46.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from absolute ethanol and benzene
color: Crystals from absolute ethanol and benzene
boiling_point: 399.6±45.0
melting_point: 189-192
solubility: Sol in alcohol, acetone, propylene glycol; practically insol in water
Descriptions:
pubchem: Carbamazepine can cause developmental toxicity according to state or federal government labeling requirements.
chebi: A dibenzoazepine that is 5<em>H</em>-dibenzo[<em>b</em>,<em>f</em>]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.
chembl: CARBAMAZEPINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Carbamazepine, sold under the brand name Tegretol among others, is an anticonvulsant medication used in the treatment of epilepsy and neuropathic pain. It is used as an adjunctive treatment in schizophrenia along with other medications and as a second-line agent in bipolar disorder. Carbamazepine appears to work as well as phenytoin and valproate for focal and generalized seizures. It is not effective for absence or myoclonic seizures.
Carbamazepine was discovered in 1953 by Swiss chemist Walter Schindler. It was first marketed in 1962. It is available as a generic medication. It is on the World Health Organization's List of Essential Medicines. In 2023, it was the 185th most commonly prescribed medication in the United States, with more than 2 million prescriptions.
Photoswitchable analogues of carbamazepine have been developed to control its pharmacological activity locally and on demand using light (photopharmacology), with the purpose of reducing the adverse systemic effects of the drug. One of these light-regulated compounds (carbadiazocine, based on a bridged azobenzene or diazocine) has been shown to produce analgesia with noninvasive illumination in vivo in a rat model of neuropathic pain.