Carbamazepine

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
Clinical data
Trade namesTegretol, others
Other namesCBZ
AHFS/Drugs.comMonograph
MedlinePlusa682237
License data
Pregnancy
category
  • AU: D
Routes of
administration
By mouth
Drug classAnticonvulsant
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
Pharmacokinetic data
Bioavailability~100%
Protein binding70–80%
MetabolismLiver (CYP3A4)
MetabolitesActive epoxide form (carbamazepine-10,11 epoxide)
Elimination half-life36 hours (single dose), 16–24 hours (repeated dosing)
ExcretionUrine (72%), feces (28%)
Identifiers
  • 5H-dibenzo[b,f]azepine-5-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.512
Chemical and physical data
FormulaC15H12N2O
Molar mass236.274 g·mol−1
3D model (JSmol)
SMILES
  • c1ccc2c(c1)C=Cc3ccccc3N2C(=O)N
  • 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) Y
  • Key:FFGPTBGBLSHEPO-UHFFFAOYSA-N Y
  (verify)

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.

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