1.0 2009-07-21 20:27:10 UTC 2026-05-14 16:42:20 UTC T3D2826 Carbamazepine SmallMolecule Carbamazepine belongs to the dibenzazepines, a subclass of benzazepines within the organic compounds. This exogenous solid has the formula C15H12N2O and an average molecular weight of 236.27 g/mol. It is classified as an organoheterocyclic compound. This drug (PMC9460350) is administered via oral or intravenous exposure routes. It is found in 29 recorded sources, including antiepileptics, drinking water, roofs, various electronic equipment, household cleaning and consumer products, and food processing activities. As an anticonvulsant, carbamazepine is used to control grand mal and psychomotor or focal seizures. It is used as a treatment for epilepsy (PMC10794432, PMC11593937, PMC5600344, PMC8587002, PMC9460350), pain (PMC3935911), neuropathic pain (PMC10534465, PMC11904242, PMC12474287, PMC5351776), depression (PMC10794432), arrhythmia (PMC10794432), and attention deficit hyperactivity disorder (PMC10989948). Additional roles include its use as an antimanic drug, an analgesic, and a non-narcotic analgesic (PMC9460350). Biologically, it acts as a mitogen, a glutamate transporter activator, and an EC 3.5.1.98 histone deacetylase inhibitor (PMC9460350). The compound targets 21 proteins, including the sodium channel protein type 5 subunit alpha (SCN5A), which it inhibits to block use-dependent sodium channels. It also inhibits the estrogen-related receptor gamma (ESRRG), hepatocyte nuclear factor 4-alpha (HNF4A), nuclear receptor ROR-beta (RORB), and the bile acid receptor (NR1H4), among others. Carbamazepine possesses sedative, muscle relaxant, antiarrhythmic, central antidiuretic, anticholinergic, and antidepressant properties. Health effects associated with the compound include Stevens-Johnson syndrome (PMC2072824), osteomalacia (PMC2646121), and epilepsy (PMC10586545). Drug Synthetic Toxin Organic Compound Amine Drug Analgesic, Non-Narcotic Anticonvulsant Antimanic Agent Analgesic Metabolite Synthetic Compound 2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaene-2-carboxamide 5-Carbamoyl-5H-dibenz(b,f)azepine 5-Carbamoyl-5H-dibenzo(b,F)azepine 5-Carbamoyl-5H-dibenz[b,F]azepine 5-Carbamyl-5H-dibenzo(b,F)azepine 5H-Dibenz(b,F)azepine-5-carboxamide Actebral Anleptic Biston Carbamat Carbamazepen Carbamazepin Carbamazepina Carbamazépine Carbamazepinum Carbamezepine Carbatrol CBZ Epitol Equetro Neurotop TEGretol TEGretol Chewtabs TEGretol-CR TEGretol-XR Teril Timonil Versitol Versizur C15H12N2O 236.2686 236.094963016 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide 298-46-4 NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12 InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18) FFGPTBGBLSHEPO-UHFFFAOYSA-N Organic compounds Organoheterocyclic compounds Benzazepines Dibenzazepines Dibenzazepines Azacyclic compounds Azepines Benzenoids Carbonyl compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Ureas Aromatic heteropolycyclic compound Azacycle Azepine Benzenoid Carbonic acid derivative Carbonyl group Dibenzazepine Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Urea Aromatic heteropolycyclic compounds dibenzoazepine ureas Detected and Not Quantified Exogenous Membrane Carbamazepine Metabolism Pathway SMP0000634 Carbamazepine Sodium Channel Analgesic Action Pathway SMP0123059 Carbamazepine Metabolism Pathway SMP0125359 Carbamazepine Drug Metabolism Action Pathway SMP0143013 Solid White powder. melting_point 204-206°C solubility 17.7 mg/L logp 2.45 logp 2.10 ALOGPS logs -3.19 ALOGPS solubility 1.52e-01 g/l ALOGPS logp 2.77 ChemAxon pka_strongest_acidic 15.96 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide ChemAxon average_mass 236.2686 ChemAxon mono_mass 236.094963016 ChemAxon smiles NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12 ChemAxon formula C15H12N2O ChemAxon inchi InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18) ChemAxon inchikey FFGPTBGBLSHEPO-UHFFFAOYSA-N ChemAxon polar_surface_area 46.33 ChemAxon refractivity 71.89 ChemAxon polarizability 25 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Oral. In clinical studies, carbamazepine suspension, conventional tablets, and extended-release tablets delivered equivalent amounts of drug to the systemic circulation. However, it has been observed that the suspension is somewhat faster absorbed. Furthermore, the extended-release tablet is slightly slower than the conventional tablet. The bioavailability of the extended-release tablet is 89%, compared to the suspension. Plasma levels of carbamazepine are variable. The time to peak concentration for the different formulations are as follows: Suspension = 1.5 hours; Conventional tablets = 4-5 hours; Extended-release tablets = 3-12 hours. Carbamazepine inhibits sustained repetitive firing by blocking use-dependent sodium channels. Pain relief is believed to be associated with blockade of synaptic transmission in the trigeminal nucleus and seizure control with reduction of post-tetanic potentiation of synaptic transmission in the spinal cord. Carbamazepine also possesses anticholinergic, central antidiuretic, antiarrhythmic, muscle relaxant, antidepressant (possibly through blockade of norepinephrine release), sedative, and neuromuscular-blocking properties. Hepatic. CYP3A4 is the primary isoform responsible for the formation of carbamazepine-10,11-epoxide. This metabolite is active and shown to be equipotent to carbamazepine as an anticonvulsant. Carbamazepine is more rapidly metabolized to the aforementioned metabolite in younger patients than in adults. It also undergoes glucuronidation via UGT2B7, however this finding has been disputed. Route of Elimination: 72% of the dose is in the urine while 28% is in the feces. Hydroxylated and conjugated metabolites are largely what was recovered in the urine. 3% of the dose is recovered as unchanged carbamazepine. Half Life: Initial half-life values range from 25-65 hours, decreasing to 12-17 hours on repeated doses. No indication of carcinogenicity to humans (not listed by IARC). For the treatment of epilepsy and pain associated with true trigeminal neuralgia. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f721fa51908> Mild ingestions cause vomiting, drowsiness, ataxia, slurred speech, nystagmus, dystonic reactions, and hallucinations. Severe intoxications may produce coma, seizures, respiratory depression, and hypotension The prognosis in cases of severe poisoning is critically dependent upon prompt elimination of the drug, which may be achieved by inducing vomiting, irrigating the stomach, and by taking appropriate steps to diminish absorption. If these measures cannot be implemented without risk on the spot, the patient should be transferred at once to a hospital, while ensuring that vital functions are safeguarded. There is no specific antidote. (L1712) DB00564 HMDB14704 2554 CHEMBL108 2457 C06868 3387 Carbamazepine Carbamazepine 15292462 18088268 Drugs.com: http://www.drugs.com/cons/Carbamazepine.html RxList: The Internet Drug Index (2009).: http://www.rxlist.com/ BE0000197 Carbamazepine inhibits sustained repetitive firing by blocking use-dependent sodium channels. Pain relief is believed to be associated with blockade of synaptic transmission in the trigeminal nucleus and seizure control with reduction of post-tetanic potentiation of synaptic transmission in the spinal cord. Carbamazepine also possesses anticholinergic, central antidiuretic, antiarrhythmic, muscle relaxant, antidepressant (possibly through blockade of norepinephrine release), sedative, and neuromuscular-blocking properties. BE0000291 Inhibitory >10 uM BindingDB 50003659 BE0000020 Inhibitory >10 uM BindingDB 50003659 BE0000442 Inhibitory >10 uM BindingDB 50003659 BE0000956 BE0002083 Inhibitory 52 uM BindingDB 50003659 BE0001143 IC50 22 uM BindingDB 50003659 BE0000132 AC50 2.93 uM Tox21_AR_BLA_Agonist_ratio Tox21/NCGC AC50 7.70 uM Tox21_AR_LUC_MDAKB2_Agonist Tox21/NCGC BE0001777 AC50 3.66 uM OT_SRC1_SRC1FXR_1440 Odyssey Thera BE0004019 AC50 4.29 uM ATG_HNF4a_TRANS Attagene BE0003554 AC50 6.72 uM ATG_RORb_TRANS Attagene BE0002088 AC50 7.03 uM ATG_ERRg_TRANS Attagene BE0000794 AC50 7.32 uM Tox21_GR_BLA_Agonist_ratio Tox21/NCGC BE0005493 AC50 7.55 uM ATG_NURR1_TRANS Attagene BE0004901 BE0000141 BE0000177 BE0000192 BE0002081 BE0002082 BE0002084 BE0000849