Carbamazepine

Not to be confused with Carbamazine.

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[1]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~100%[5]
Protein binding70–80%[5]
MetabolismLiver (CYP3A4)[5]
MetabolitesActive epoxide form (carbamazepine-10,11 epoxide)[5]
Elimination half-life36 hours (single dose), 16–24 hours (repeated dosing)[5]
ExcretionUrine (72%), feces (28%)[5]
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 Edit this at Wikidata
Chemical and physical data
FormulaC15H12N2O
Molar mass236.274 g·mol−1
3D model (JSmol)
  • 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) checkY
  • Key:FFGPTBGBLSHEPO-UHFFFAOYSA-N checkY
  (verify)

Carbamazepine, sold under the brand name Tegretol among others, is an anticonvulsant medication used in the treatment of epilepsy and neuropathic pain.[4][1] It is used as an adjunctive treatment in schizophrenia along with other medications and as a second-line agent in bipolar disorder.[6][1] Carbamazepine appears to work as well as phenytoin and valproate for focal and generalized seizures.[7] It is not effective for absence or myoclonic seizures.[1]

Carbamazepine was discovered in 1953 by Swiss chemist Walter Schindler.[8][9] It was first marketed in 1962.[10] It is available as a generic medication.[11] It is on the World Health Organization's List of Essential Medicines.[12] In 2020, it was the 185th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[13][14]

Photoswitchable analogues of carbamazepine have been developed to control its pharmacological activity locally and on demand using light, with the purpose to reduce adverse systemic effects.[15] One of these compounds (carbadiazocine, based on a bridged azobenzene) has been shown to produce analgesia with noninvasive illumination in a rat model of neuropathic pain.

  1. ^ a b c d "Carbamazepine". The American Society of Health-System Pharmacists. Archived from the original on 27 February 2015. Retrieved 28 March 2015.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ a b "Tegretol- carbamazepine suspension Tegretol- carbamazepine tablet Tegretol XR- carbamazepine tablet, extended release". DailyMed. 16 May 2022. Retrieved 3 January 2023.
  5. ^ a b c d e f Cite error: The named reference carbamazepinelabel was invoked but never defined (see the help page).
  6. ^ Nevitt SJ, Marson AG, Weston J, Tudur Smith C (August 2018). "Sodium valproate versus phenytoin monotherapy for epilepsy: an individual participant data review". The Cochrane Database of Systematic Reviews. 2018 (8): CD001769. doi:10.1002/14651858.CD001769.pub4. PMC 6513104. PMID 30091458.
  7. ^ Nevitt SJ, Marson AG, Tudur Smith C (July 2019). "Carbamazepine versus phenytoin monotherapy for epilepsy: an individual participant data review". The Cochrane Database of Systematic Reviews. 2019 (7): CD001911. doi:10.1002/14651858.CD001911.pub4. PMC 6637502. PMID 31318037.
  8. ^ Smith HS (2009). Current therapy in pain. Philadelphia: Saunders/Elsevier. p. 460. ISBN 978-1-4160-4836-7. Archived from the original on 5 March 2016.
  9. ^ US patent 2948718, Walter Schindler, "New n-heterocyclic compounds", published 1960-08-09, issued 1960-08-09, assigned to Geigy Chemical Corporation 
  10. ^ Moshé S (2009). The treatment of epilepsy (3 ed.). Chichester, UK: Wiley-Blackwell. p. xxix. ISBN 978-1-4443-1667-4. Archived from the original on 5 March 2016.
  11. ^ Porter NC (2008). "Trigeminal Neuralgia: Surgical Perspective". In Chin LS, Regine WF (eds.). Principles and practice of stereotactic radiosurgery. New York: Springer. p. 536. ISBN 978-0-387-71070-9. Archived from the original on 5 March 2016.
  12. ^ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  13. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  14. ^ "Carbamazepine - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  15. ^ Camerin L, Maleeva G, Gomila-Juaneda A, Suárez-Pereira I, Matera C, Prischich D, et al. (June 2024). "Photoswitchable carbamazepine analogs for non-invasive neuroinhibition in vivo". Angewandte Chemie: e202403636. doi:10.1002/anie.202403636. hdl:2445/215169. PMID 38887153.