Carbamazepine

Carbamazepine
Clinical data
Trade names	Tegretol, others
Other names	CBZ
AHFS/Drugs.com	Monograph
MedlinePlus	a682237
License data	US DailyMed: Carbamazepine;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
Drug class	Anticonvulsant
ATC code	N03AF01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	~100%
Protein binding	70–80%
Metabolism	Liver (CYP3A4)
Metabolites	Active epoxide form (carbamazepine-10,11 epoxide)
Elimination half-life	36 hours (single dose), 16–24 hours (repeated dosing)
Excretion	Urine (72%), feces (28%)
Identifiers
	IUPAC name 5H-dibenzo[b,f]azepine-5-carboxamide;
CAS Number	298-46-4 85756-57-6;
PubChem CID	2554;
IUPHAR/BPS	5339;
DrugBank	DB00564 ;
ChemSpider	2457 ;
UNII	33CM23913M;
KEGG	D00252 ;
ChEBI	CHEBI:3387 ;
ChEMBL	ChEMBL108 ;
CompTox Dashboard (EPA)	DTXSID4022731 ;
ECHA InfoCard	100.005.512
Chemical and physical data
Formula	C15H12N2O
Molar mass	236.274 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccc2c(c1)C=Cc3ccccc3N2C(=O)N;
	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) ; Key:FFGPTBGBLSHEPO-UHFFFAOYSA-N ;
	(verify)

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 2020, 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.