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Topiramate information


Topiramate
Clinical data
Trade namesTopamax, Trokendi XR, Qudexy XR, others
Other namesTopiramic acid
AHFS/Drugs.comMonograph
MedlinePlusa697012
License data
  • US DailyMed: Topiramate
Pregnancy
category
  • AU: D
Routes of
administration
Oral
ATC code
  • N03AX11 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[2]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only[3][4][5][6][7]
  • EU: Rx-only[8]
Pharmacokinetic data
Bioavailability80%
Protein binding13–17%; 15–41%
MetabolismLiver (20–30%)
Elimination half-life21 hours
ExcretionUrine (70–80%)
Identifiers
IUPAC name
  • 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
CAS Number
  • 97240-79-4 checkY
PubChem CID
  • 5284627
IUPHAR/BPS
  • 6849
DrugBank
  • DB00273 ☒N
ChemSpider
  • 4447672 checkY
UNII
  • 0H73WJJ391
KEGG
  • D00537 checkY
ChEMBL
  • ChEMBL220492 checkY
PDB ligand
  • TOR (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID8023688 Edit this at Wikidata
ECHA InfoCard100.129.713 Edit this at Wikidata
Chemical and physical data
FormulaC12H21NO8S
Molar mass339.36 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=S(=O)(OC[C@@]21OC(O[C@H]1[C@@H]3OC(O[C@@H]3CO2)(C)C)(C)C)N
InChI
  • 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 2021, it was the 66th most commonly prescribed medication in the United States, with more than 10 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, MGH Center for Women's Mental (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 2021". ClinCalc. Retrieved 14 January 2024.
  18. ^ "Topiramate - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Topiramate

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Topiramate, sold under the brand name Topamax among others, is a medication used to treat epilepsy and prevent migraines. It has also been used in alcohol...

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Phentermine

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benefits subside. It is also available as the combination phentermine/topiramate. Common side effects include a fast heart beat, high blood pressure, trouble...

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Anticonvulsant

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Tiagabine (1996). Vigabatrin and progabide are also analogs of GABA. Topiramate (1995). Gabapentinoids are used in epilepsy, neuropathic pain, fibromyalgia...

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Epilepsy and pregnancy

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ASMs. Clobazam, eslicarbazepine, felbamate, lamotrigine, rufinamide and topiramate are examples of weak enzyme-inducing ASMs. Non-enzyme-inducing ASMs do...

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Alcoholism

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abuse alcohol. Topiramate is a derivative of the naturally occurring sugar monosaccharide D-fructose. Review articles characterize topiramate as showing "encouraging"...

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Death of Kenneka Jenkins

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examiner's report found Jenkins' death to be accidental. Alcohol and topiramate found in her system were thought to have hastened the effects of hypothermia...

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Ketamine

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Oxitriptyline Phenacemide Pheneturide Phenytoin Rufinamide Sipatrigine Topiramate Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium Valproic...

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Phenyltriazines

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(1998). "Newer antiepileptic drugs: Gabapentin, lamotrigine, felbamate, topiramate and fosphenytoin". American Family Physician. 57 (3): 513–20. PMID 9475899...

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Palinopsia

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head trauma, or may be idiopathic. Trazodone, nefazodone, mirtazapine, topiramate, clomiphene, oral contraceptives, and risperidone have been reported to...

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Vivus

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and topiramate, two existing weight-loss drugs. On July 17, 2012, The U.S. Food and Drug Administration approved Qsymia (phentermine and topiramate extended-release)...

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Zonisamide

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toxic effects Zonisamide and other carbonic anhydrase inhibitors such as topiramate, furosemide, and hydrochlorothiazide have been known to interfere with...

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Zinc

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Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g.,...

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Cocaine

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Oxitriptyline Phenacemide Pheneturide Phenytoin Rufinamide Sipatrigine Topiramate Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium Valproic...

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Alprazolam

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sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic...

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Amitriptyline

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similar in efficancy to venlafaxine and topiramate but carries a higher burden of adverse effects than topiramate. For many patients, even very small doses...

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Fluoxetine

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sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic...

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Tramadol

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Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g.,...

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Anna Nicole Smith

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(diazepam). Furthermore, she had taken Benadryl (diphenhydramine) and Topamax (topiramate), both of which block sodium channels, likely intensifying the sedative...

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Toluene

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sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic...

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Cocaine dependence

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Anticonvulsants, such as carbamazepine, gabapentin, lamotrigine, and topiramate, do not appear to be effective as treatment. Limited evidence suggests...

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Midazolam

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sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic...

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Obesity

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phentermine–topiramate is available only in the United States. European regulatory authorities rejected lorcaserin and phentermine-topiramate, in part because...

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Glutamine

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baicalin) Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal)) Topiramate Valerian constituents (e.g., valerenic acid) Volatiles/gases (e.g., chloral...

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Persistent aura without infarction

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been tried as treatment, notably acetazolamide, valproate, lamotrigine, topiramate, and furosemide. Chen, WT; Fuh, JL; Lu, SR; Wang, SJ (September 2001)...

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Saffron

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Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g.,...

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Methoxyflurane

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sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic...

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Dravet syndrome

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reduced by anticonvulsant medications such as clobazam, stiripentol, topiramate and valproate. Because the course of the disorder varies from individual...

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Illusory palinopsia

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94% described illusory palinopsia. Trazodone, nefazodone, mirtazapine, topiramate, clomiphene, oral contraceptives, and risperidone have been reported to...

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List of psychiatric medications

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