Topiramate

Topiramate
Clinical data
Trade namesTopamax, Trokendi XR, Qudexy XR, others
Other namesTopiramic acid
AHFS/Drugs.comMonograph
MedlinePlusa697012
License data
Pregnancy
category
  • AU: D
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80%
Protein binding13–17%; 15–41%
MetabolismLiver (20–30%)
Elimination half-life21 hours
ExcretionUrine (70–80%)
Identifiers
  • 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.129.713 Edit this at Wikidata
Chemical and physical data
FormulaC12H21NO8S
Molar mass339.36 g·mol−1
3D model (JSmol)
  • O=S(=O)(OC[C@@]21OC(O[C@H]1[C@@H]3OC(O[C@@H]3CO2)(C)C)(C)C)N
  • InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1 checkY
  • Key:KJADKKWYZYXHBB-XBWDGYHZSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Topiramate, sold under the brand name Topamax among others, is a medication used to treat epilepsy and prevent migraines.[9] It has also been used in alcohol dependence and essential tremor.[9] For epilepsy this includes treatment for generalized or focal seizures.[10] It is taken orally (by mouth).[9]

Common side effects include tingling, feeling tired, loss of appetite, abdominal pain, weight loss,[11] and decreased cognitive function such as trouble concentrating.[9][10] Serious side effects may include suicide, increased ammonia levels resulting in encephalopathy, and kidney stones.[9] Topiramate can cause birth defects including cleft lip and palate.[12] Risk/benefit should be carefully discussed with the full treatment team. Topiramate is considered "probably compatible" with lactation and is not contraindicated in breastfeeding, though monitoring of the infant for diarrhea or poor weight gain may be considered.[13][14] The mechanism of action is unclear.[9]

Topiramate was approved for medical use in the United States in 1996.[9] It is available as a generic medication.[10][15][16] In 2022, it was the 84th most commonly prescribed medication in the United States, with more than 8 million prescriptions.[17][18]

  1. ^ "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.
  2. ^ 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.
  3. ^ "Trokendi XR- topiramate capsule, extended release". DailyMed. Archived from the original on 8 November 2021. Retrieved 8 November 2021.
  4. ^ "Topamax- topiramate tablet, coated Topamax- topiramate capsule, coated pellets". DailyMed. Archived from the original on 8 November 2021. Retrieved 8 November 2021.
  5. ^ "Qsymia- phentermine and topiramate capsule, extended release". DailyMed. Archived from the original on 26 October 2021. Retrieved 8 November 2021.
  6. ^ "Qudexy XR- topiramate capsule, extended release". DailyMed. Archived from the original on 8 November 2021. Retrieved 8 November 2021.
  7. ^ "Eprontia - topiramate solution". DailyMed. Archived from the original on 19 December 2021. Retrieved 19 December 2021.
  8. ^ "Active substance(s): topiramate" (PDF). List of nationally authorised medicinal products. European Medicines Agency. September 2022. Archived (PDF) from the original on 6 September 2022. Retrieved 6 September 2022.
  9. ^ a b c d e f g "Topiramate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 6 March 2019. Retrieved 5 March 2019.
  10. ^ a b c British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 328. ISBN 9780857113382.
  11. ^ "Topiramate Side Effects: Common, Severe, Long Term". Drugs.com. Archived from the original on 10 April 2021. Retrieved 3 August 2021.
  12. ^ "FDA Drug Safety Communication: Risk of oral clefts in children born to mothers taking Topamax (topiramate)". FDA. 18 June 2019.
  13. ^ Health MC (10 August 2022). "Essential Reads: Breastfeeding and Anti-Epileptic Drugs - MGH Center for Women's Mental Health". Retrieved 27 December 2023.
  14. ^ "Topiramate", Drugs and Lactation Database (LactMed®), Bethesda (MD): National Institute of Child Health and Human Development, 2006, PMID 30000318, retrieved 27 December 2023
  15. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  16. ^ "First Generic Drug Approvals 2023". U.S. Food and Drug Administration (FDA). 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Topiramate Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.