Carbamazepine

Title: Carbamazepine
CAS Registry Number: 298-46-4
CAS Name: 5H-Dibenz[b,f]azepine-5-carboxamide
Additional Names: 5-carbamoyl-5H-dibenz[b,f]azepine
Manufacturers' Codes: G-32883
Trademarks: Biston (Slovakofarma); Calepsin (Orion); Carbatrol (Shire); Epitol (Teva); Finlepsin (AWD); Sirtal (Dura); Stazepine (Polfa); Tegretol (Novartis); Telesmin (Yoshitomi); Timonil (Desitin)
Molecular Formula: C15H12N2O
Molecular Weight: 236.27
Percent Composition: C 76.25%, H 5.12%, N 11.86%, O 6.77%
Literature References: Prepn: W. Schindler, US 2948718 (1960 to Geigy). Toxicity: E. G. Stenger, F. C. Roulet, Med. Exp. 11, 191 (1964). Review of GLC methods, pharmacokinetics and metabolism: S. Pynnönen, Ther. Drug Monit. 1, 409-431 (1979). Comprehensive description: H. Y. Aboul-Enein, A. A. Al-Badr, Anal. Profiles Drug Subs. 9, 87-106 (1980). Review of clinical use in pediatric seizures: J. T. Gilman, DICP Ann. Pharmacother. 25, 1109-1112 (1991); in trigeminal neuralgia: A. Sidebottom, S. Maxwell, J. Clin. Pharm. Ther. 20, 31-35 (1995).
Properties: Crystals from abs ethanol + benzene, mp 190-193°. Sol in alcohol, acetone, propylene glycol. Practically insol in water. LD50 orally in mice, rats: 3750, 4025 mg/kg (Stenger, Roulet).
Melting point: mp 190-193°
Toxicity data: LD50 orally in mice, rats: 3750, 4025 mg/kg (Stenger, Roulet)
Therap-Cat: Anticonvulsant. In treatment of pain associated with trigeminal neuralgia.
Keywords: Anticonvulsant.
Carbamide Peroxide Carbamyl Chloride Carbanilic Acid Carbanilide Carbarsone

Carbamazepine
Carbamazepine.svg
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Systematic (IUPAC) name
5H-dibenzo[b,f]azepine-5-carboxamide
Clinical data
Trade names Tegretol
AHFS/Drugs.com monograph
MedlinePlus a682237
Licence data US Daily Med:link
Pregnancy cat. D (AU) D (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability ~100%[1]
Protein binding 70-80%[1]
Metabolism Hepatic—by CYP3A4, to active epoxide form (carbamazepine-10,11 epoxide)[1]
Half-life 36 hours (single dose), 16-24 hours (repeated dosing)[1]
Excretion Urine (72%), faeces (28%)[1]
Identifiers
CAS number 298-46-4 YesY 85756-57-6
ATC code N03AF01
PubChem CID 2554
DrugBank DB00564
ChemSpider 2457 YesY
UNII 33CM23913M YesY
KEGG D00252 YesY
ChEBI CHEBI:3387 YesY
ChEMBL CHEMBL108 YesY
Chemical data
Formula C15H12N2O 
Mol. mass 236.269 g/mol
 YesY (what is this?)  (verify)

Carbamazepine (CBZ) (Tegretol, Equetro) is an anticonvulsant and mood-stabilizing drug used primarily in the treatment of epilepsy and bipolar disorder, as well as trigeminal neuralgia. It is also used off-label for a variety of indications, including attention-deficit hyperactivity disorder (ADHD), schizophrenia, phantom limb syndrome, complex regional pain syndrome, paroxysmal extreme pain disorder, neuromyotonia, intermittent explosive disorder, borderline personality disorder, Myotonia congenita and post-traumatic stress disorder.

Like other anticonvulsants, intrauterine exposure is associated with spina bifida[2] and neurodevelopmental problems.[3]