Back كاربامازيبين Arabic Carbamazepina Catalan Carbamasepin Welsh Carbamazepin German Καρβαμαζεπίνη Greek Karbamazepino Esperanto Carbamazepina Spanish Karbamazepina Basque کاربامازپین Persian Karbamatsepiini Finnish

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. PMID 38887153.

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