Structure via PubChem · Public domain (PubChem)
topiramate
Sign in to saveAlso known as TPM, 2,3:4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate, 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose sulfamate, [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecan-6-yl]methyl sulfamate
Topiramate, marketed as Topamax and other brand names, is an oral medication primarily prescribed for the treatment of epilepsy and the prophylaxis of migraines. For epilepsy, this includes treatment for generalized or focal seizures. It has also been used off-label for alcohol dependence and essential tremor.
Key facts
- Drug.pregnancy_AU
- D
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 408971931
- Drug.image
- Topiramate structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 175
- Drug.image2
- Topiramate 3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Topamax, Trokendi XR, Qudexy XR, others
- Drug.MedlinePlus
- a697012
- Drug.DailyMedID
- Topiramate
- Drug.routes_of_administration
- Oral
- Drug.ATC_prefix
- N03
- Drug.ATC_suffix
- AX11
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
- Drug.legal_CA
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C12H21NO8S
- Molecular weight
- 339.36 g/mol
- IUPAC name
- [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl sulfamate
- SMILES
- CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C
- InChIKey
- KJADKKWYZYXHBB-XBWDGYHZSA-N
- XLogP
- -0.8
- Polar surface area
- 124 Ų
- H-bond donors
- 1
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Research
6,484 papers- Narrative Review of Topiramate: Clinical Uses and Pharmacological Considerations.Advances in therapy · 2023
- Phentermine/Topiramate: Pediatric First Approval.Paediatric drugs · 2022
- Topiramate for juvenile myoclonic epilepsy.The Cochrane database of systematic reviews · 2019
- Topiramate Versus Naltrexone for Alcohol Use Disorder: A Genotype-Stratified Double-Blind Randomized Controlled Trial.The American journal of psychiatry · 2024
- Topiramate for Weight Management in Children With Severe Obesity.Childhood obesity (Print) · 2023
via PubMed
~12 min read
Encyclopedic overview
13 sectionsContents
- Medical uses
- Pain
- Other
- Adverse effects
- Frequency
- Overdose
- Interactions
- Pharmacology
- Detection in body fluids
- History
- Research
- References
- External links
Topiramate, marketed as Topamax and other brand names, is an oral medication primarily prescribed for the treatment of epilepsy and the prophylaxis of migraines. For epilepsy, this includes treatment for generalized or focal seizures. It has also been used off-label for alcohol dependence and essential tremor.
Common side effects include tingling, feeling tired, loss of appetite, abdominal pain, weight loss, and decreased cognitive function such as trouble concentrating. Serious side effects may include suicidal ideation, increased ammonia levels resulting in encephalopathy, and kidney stones. Topiramate can cause birth defects, including cleft lip and palate. Risks/benefits should be carefully discussed with the full treatment team. Topiramate is considered "probably compatible" with lactation and is not contraindicated for breastfeeding, though monitoring of the infant for diarrhea or poor weight gain may be considered. Its mechanism of action is unclear.
Excerpted from Wikipedia’s “topiramate” article, available under the CC BY-SA 4.0 licence.