Topiramate

Identification

Summary

Topiramate is an anticonvulsant drug used in the control of epilepsy and in the prophylaxis and treatment of migraines.

Brand Names
Eprontia, Qsymia, Qudexy, Topamax, Trokendi
Generic Name
Topiramate
DrugBank Accession Number
DB00273
Background

Topiramate is a anti-epileptic drug used to manage seizures and prevent migraines.4 It was initially approved by the FDA in 1996. In 2004, topiramate was approved for the prevention of migraine in adults.6,19,23 Since 2012, the extended-release formulation has been approved in combination with phentermine for chronic weight management therapy in adults.21

Characteristics that distinguish topiramate from other antiepileptic drugs are a monosaccharide chemical structure containing a sulfamate, and 40% of its mass accounted for by oxygen.4 Interestingly, topiramate was discovered by chance when attempts were made to formulate a novel antidiabetic drug.8

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 339.362
Monoisotopic: 339.098787343
Chemical Formula
C12H21NO8S
Synonyms
  • 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
  • 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose sulfamate
  • Tipiramate
  • Tipiramato
  • Topiramate
  • Topiramato
  • Topiramatum
  • TPM
External IDs
  • MCN-4853
  • RWJ-17021
  • RWJ-17021-000
  • USL-255
  • USL255

Pharmacology

Indication

Topiramate is indicated for the following conditions: 1)Monotherapy for partial onset or primary generalized tonic-clonic seizures for patients 2 years of age and above 2)Adjunctive therapy for partial onset seizures or primary generalized tonic-clonic seizures for both adult and pediatric patients above 2 years old 3)Adjunctive therapy for seizures associated with Lennox-Gastaut syndrome in patients above 2 years of age 4)Prophylaxis of migraine in children 12 years of age and older and adults.19

Topiramate is also used off-label as an adjunct therapy for weight management21 and for mood disorders.7

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAlcohol dependence••• •••••••••••
Adjunct therapy in management ofEpilepsy, primary generalized tonic-clonic seizures•••••••••••••••••••• •••••••• •••••••
Management ofEpilepsy, primary generalized tonic-clonic seizures•••••••••••••••••••• •••••••• •••••••
Adjunct therapy in management ofLennox-gastaut syndrome•••••••••••••••••••• ••••••••• ••••••
Prophylaxis ofMigraine•••••••••••••••••••• •••••••• •••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Topiramate prevents the occurrence of seizures and prevents migraine symptoms by reducing neural pathway excitability.8,19 It is important to note that this drug may cause metabolic acidosis, mood changes, suicidal thoughts and attempts, as well as kidney stones. When topiramate is combined with valproic acid, it is known to cause hypothermia.19

Mechanism of action

A seizure is an abnormal and unregulated electrical discharge occurring in the brain. This leads to transient interruption in brain function, manifested by reduced alertness, abnormal sensations, and focal involuntary movements or convulsions. Several types of seizures exist, with common types including tonic-clonic seizures and partial onset seizures.17

The exact mechanisms by which topiramate exerts pharmacological actions on seizures and migraines are currently not fully characterized.10,19 Several properties of this drug, however, are likely to contribute to its therapeutic effects. Topiramate has been observed to exert actions on voltage-dependent sodium channels, GABA receptors, and glutamate receptors.4,19

Topiramate stimulates GABA-A receptor activity at brain non-benzodiazepine receptor sites and reduces glutamate activity at both AMPA and kainate receptors. Normally, GABA-A receptors are inhibitory and glutaminergic receptors are stimulatory for neuronal activity.15,16 By increasing GABA activity and inhibiting glutamate activity, topiramate blocks neuronal excitability, preventing seizures and migraines.9,6,19 Additionally, it blocks the voltage-dependent sodium channels, further blocking seizure activity.15 Topiramate has been shown to inhibit various carbonic anhydrase isozymes, but the clinical significance of this is unknown at this time.11,12,13,19

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
agonist
Humans
AVoltage-gated sodium channel alpha subunit
inhibitor
Humans
AKainate receptors
antagonist
Humans
ACarbonic anhydrase 2
inhibitor
Humans
ACarbonic anhydrase 4
inhibitor
Humans
AVoltage gated L-type calcium channel
antagonist
Humans
UCarbonic anhydrase 1
inhibitor
Humans
UCarbonic anhydrase 3
inhibitor
Humans
UVoltage-dependent R-type calcium channel
antagonist
Humans
Absorption

After a 400mg dose in one clinical trial, topiramate reached maximal concentrations within 1.8-4.3 hours and ranged from 1.73-28.7 ug/mL. Food did not significantly affect the extent of absorption, despite delaying time to peak concentration. In patients with normal creatinine clearance, steady state concentrations are reached within 4 days.3 The bioavailability of topiramate in tablet form is about 80% compared to a topiramate solution.19

Volume of distribution

The mean apparent volume of distribution of topiramate ranges from 0.6-0.8 L/kg when doses of 100mg to 1200mg are given.3 Topiramate readily crosses the blood-brain barrier.4

Protein binding

Topiramate is not highly bound to plasma proteins, with an estimated plasma protein binding of 9-17% according to some studies.3,4 The FDA label indicates that the protein binding of topiramate is 15-41%.19

Metabolism

The metabolites of topiramate are not known to be active.2 The metabolism of topiramate is characterized by reactions of glucuronidation, hydroxylation and hydrolysis that lead to the production of six minor metabolites.19 Some of topiramate's metabolites include 2,3-desisopropylidene topiramate, 4,5-desisopropylidene topiramate, 9-hydroxy topiramate, and 10-hydroxy topiramate.14

Hover over products below to view reaction partners

Route of elimination

Topiramate is mainly eliminated through the kidneys.15 About 70-80% of the eliminated dose is found unchanged in the urine.3,19

Half-life

The elimination half-life is reported to be in the range of 19-23 hours.3 If topiramate is given with enzyme-inducers, the half-life can be reduced to 12-15 hours because of increased metabolism.3

Clearance

The mean oral plasma clearance of topiramate ranges from 22-36 mL/min while the renal clearance is 17-18 mL/min, according to one pharmacokinetic study.3 The FDA label for topiramate indicates a similar oral plasma clearance of approximately 20 to 30 mL/min in adults.19

Adverse Effects
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Toxicity

The LD50 of intraperitoneal topiramate in the rat is above 1500 mg/kg.20

Overdose information

In a study of 4 healthy adult women taking topiramate, the severity of clinical effects following an overdose ranged from asymptomatic to severe, with no deaths reported.5 According to the FDA prescribing information for topiramate, an overdose may cause hypotension, severe metabolic acidosis, coma, abdominal pain, visual disturbances, convulsions, drowsiness, speech abnormalities, impaired mentation and coordination, stupor, agitation, dizziness, as well as depression.19

In the case of a recent ingestion of topiramate, the stomach contents should be emptied through the induction of emesis or gastric lavage. Offer supportive treatment, including activated charcoal and hemodialysis.19

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Topiramate is combined with 1,2-Benzodiazepine.
AbacavirTopiramate may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Topiramate.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Topiramate.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Topiramate.
Food Interactions
  • Avoid a ketogenic diet. This type of diet increases the risk of kidney stones.
  • Take with or without food. Food slightly alters absorption but not to any clinically significant extent.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Topiramate calciumP956SY6RA61246279-00-4VNRLRDKZOMPUAG-RZTSBURASA-N
Topiramate potassiumSMU8E1YBZ3488127-51-1VEKVPJSPZRTTGR-WGAVTJJLSA-N
Topiramate sodiumN808MSN0PT488127-49-7ZUWVVMMRNQEJMW-WGAVTJJLSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EprontiaSolution25 mg/1mLOralAzurity Pharmaceuticals, Inc.2021-12-06Not applicableUS flag
Gln-topiramateTablet200 mgOralGlenmark Pharmaceuticals, Inc2007-07-12Not applicableCanada flag
Gln-topiramateTablet25 mgOralGlenmark Pharmaceuticals, IncNot applicableNot applicableCanada flag
Gln-topiramateTablet200 mgOralGlenmark Pharmaceuticals, IncNot applicableNot applicableCanada flag
Gln-topiramateTablet100 mgOralGlenmark Pharmaceuticals, Inc2007-07-12Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Abbott-topiramateTablet25 mgOralBgp Pharma Ulc2014-03-122015-12-31Canada flag
Abbott-topiramateTablet200 mgOralBgp Pharma Ulc2014-03-172015-12-31Canada flag
Abbott-topiramateTablet100 mgOralBgp Pharma Ulc2014-03-122015-12-31Canada flag
Accel-topiramateTablet200 mgOralAccel Pharma Inc2015-03-262017-01-27Canada flag
Accel-topiramateTablet100 mgOralAccel Pharma Inc2015-03-262017-01-27Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
QsymiaTopiramate (46 mg/1) + Phentermine hydrochloride (7.5 mg/1)Capsule, extended releaseOralVIVUS LLC2012-09-17Not applicableUS flag
QsymiaTopiramate (69 mg/1) + Phentermine hydrochloride (11.25 mg/1)Capsule, extended releaseOralVIVUS LLC2012-09-17Not applicableUS flag
QsymiaTopiramate (23 mg/1) + Phentermine hydrochloride (3.75 mg/1)Capsule, extended releaseOralVIVUS LLC2012-09-17Not applicableUS flag
QsymiaTopiramate (92 mg/1) + Phentermine hydrochloride (15 mg/1)Capsule, extended releaseOralVIVUS LLC2012-09-17Not applicableUS flag

Categories

ATC Codes
A08AA51 — Phentermine and topiramateN03AX11 — Topiramate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dioxolopyrans. These are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Dioxolopyrans
Sub Class
Not Available
Direct Parent
Dioxolopyrans
Alternative Parents
Ketals / Oxanes / Monosaccharides / Organic sulfuric acids and derivatives / 1,3-dioxolanes / Oxacyclic compounds / Organic oxides / Organic nitrogen compounds / Hydrocarbon derivatives
Substituents
Acetal / Aliphatic heteropolycyclic compound / Dioxolopyran / Hydrocarbon derivative / Ketal / Meta-dioxolane / Monosaccharide / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cyclic ketal, sulfamate ester, ketohexose derivative (CHEBI:63631)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0H73WJJ391
CAS number
97240-79-4
InChI Key
KJADKKWYZYXHBB-XBWDGYHZSA-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
IUPAC Name
[(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
SMILES
[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2

References

Synthesis Reference

Geza Arvai, Sandor Garaczi, Attila Mate, Ferenc Lukacs, Zsolt Viski, Geza Schneider.(2004).US20060040874A1.Retrieved from: https://patents.google.com/patent/US20060040874A1/en.

US20040053853
General References
  1. Ford L, Goldberg JL, Selan F, Greenberg HE, Shi Y: Comprehensive review of visual defects reported with topiramate. Clin Ophthalmol. 2017 May 23;11:983-992. doi: 10.2147/OPTH.S125768. eCollection 2017. [Article]
  2. Brigo F, Bragazzi NL, Igwe SC, Nardone R, Trinka E: Topiramate in the Treatment of Generalized Convulsive Status Epilepticus in Adults: A Systematic Review with Individual Patient Data Analysis. Drugs. 2017 Jan;77(1):67-74. doi: 10.1007/s40265-016-0672-2. [Article]
  3. Garnett WR: Clinical pharmacology of topiramate: a review. Epilepsia. 2000;41 Suppl 1:S61-5. [Article]
  4. Shank RP, Gardocki JF, Streeter AJ, Maryanoff BE: An overview of the preclinical aspects of topiramate: pharmacology, pharmacokinetics, and mechanism of action. Epilepsia. 2000;41 Suppl 1:S3-9. [Article]
  5. Wisniewski M, Lukasik-Glebocka M, Anand JS: Acute topiramate overdose--clinical manifestations. Clin Toxicol (Phila). 2009 Apr;47(4):317-20. doi: 10.1080/15563650601117954. [Article]
  6. Wenzel RG, Schwarz K, Padiyara RS: Topiramate for migraine prevention. Pharmacotherapy. 2006 Mar;26(3):375-87. doi: 10.1592/phco.26.3.375. [Article]
  7. Arnone D: Review of the use of Topiramate for treatment of psychiatric disorders. Ann Gen Psychiatry. 2005 Feb 16;4(1):5. doi: 10.1186/1744-859X-4-5. [Article]
  8. Maryanoff BE: Sugar sulfamates for seizure control: discovery and development of topiramate, a structurally unique antiepileptic drug. Curr Top Med Chem. 2009;9(11):1049-62. doi: 10.2174/156802609789630938. [Article]
  9. Chung JY, Kim MW, Kim M: Efficacy of zonisamide in migraineurs with nonresponse to topiramate. Biomed Res Int. 2014;2014:891348. doi: 10.1155/2014/891348. Epub 2014 Jul 2. [Article]
  10. Naegel S, Obermann M: Topiramate in the prevention and treatment of migraine: efficacy, safety and patient preference. Neuropsychiatr Dis Treat. 2010 Feb 3;6:17-28. doi: 10.2147/ndt.s6459. [Article]
  11. Maryanoff BE, McComsey DF, Costanzo MJ, Hochman C, Smith-Swintosky V, Shank RP: Comparison of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II by using topiramate as a structural platform. J Med Chem. 2005 Mar 24;48(6):1941-7. [Article]
  12. Dodgson SJ, Shank RP, Maryanoff BE: Topiramate as an inhibitor of carbonic anhydrase isoenzymes. Epilepsia. 2000;41 Suppl 1:S35-9. doi: 10.1111/j.1528-1157.2000.tb06047.x. [Article]
  13. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [Article]
  14. Caldwell GW, Wu WN, Masucci JA, McKown LA, Gauthier D, Jones WJ, Leo GC, Maryanoff BE: Metabolism and excretion of the antiepileptic/antimigraine drug, Topiramate in animals and humans. Eur J Drug Metab Pharmacokinet. 2005 Jul-Sep;30(3):151-64. doi: 10.1007/BF03190614. [Article]
  15. Walker MC, Sander JW: Topiramate: a new antiepileptic drug for refractory epilepsy. Seizure. 1996 Sep;5(3):199-203. [Article]
  16. Mary J. Allen; Sandeep Sharma (2019). GABA receptor. StatPearls.
  17. Merck [Link]
  18. Topamax, manufacturer's website [Link]
  19. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]
  20. MSDS, Topiramate [Link]
  21. Qsymia approval information [Link]
  22. FDA Approved Drug Products: Qsymia (phentermine and topiramate), extended-release capsules for oral use [Link]
  23. FDA Approved Drug Products: TROKENDI XR (topiramate) extended-release capsules for oral use [Link]
Human Metabolome Database
HMDB0005034
KEGG Drug
D00537
KEGG Compound
C07502
PubChem Compound
5284627
PubChem Substance
46508334
ChemSpider
4447672
BindingDB
10887
RxNav
38404
ChEBI
63631
ChEMBL
CHEMBL220492
ZINC
ZINC000095616603
Therapeutic Targets Database
DAP000137
PharmGKB
PA451728
PDBe Ligand
TOR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Topiramate
PDB Entries
3hku / 3lxe / 5jna / 7yg5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentObesity1
4Active Not RecruitingTreatmentObesity / Type 2 Diabetes Mellitus1
4CompletedEducational/Counseling/TrainingRestless Legs Syndrome (RLS)1
4CompletedOtherDecline, Cognitive1
4CompletedPreventionMigraine3

Pharmacoeconomics

Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
  • Barr laboratories inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
  • Accord healthcare inc
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd
  • Cipla ltd
  • Glenmark generics ltd
  • Invagen pharmaceuticals inc
  • Pliva hrvatska doo
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Sun pharmaceutical industries ltd
  • Torrent pharmaceuticals ltd
  • Unichem laboratories ltd
  • Upsher smith laboratories inc
Packagers
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Avkare Incorporated
  • Barr Pharmaceuticals
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • Cadila Healthcare Ltd.
  • Camber Pharmaceuticals Inc.
  • Cardinal Health
  • Cipla Ltd.
  • Cobalt Pharmaceuticals Inc.
  • Comprehensive Consultant Services Inc.
  • DAVA Pharmaceuticals
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Ethypharm
  • Gallipot
  • Glenmark Generics Ltd.
  • Greenstone LLC
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • InvaGen Pharmaceuticals Inc.
  • Janssen-Ortho Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • McNeil Laboratories
  • Medisca Inc.
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Shanghai Junjie Biotechnology Co. Ltd.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Torrent Pharmaceuticals
  • UDL Laboratories
  • Unichem Laboratories Ltd.
  • Upsher Smith Laboratories
  • Vangard Labs Inc.
  • Zydus Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral100.0000 mg
Tablet, film coatedOral
SolutionOral25 mg/1mL
CapsuleOral5.000 mg
TabletOral100.000 mg
Tablet, film coatedOral100 mg
Tablet, film coatedOral25 mg
TabletOral50 mg
Capsule, extended releaseOral
Capsule, extended releaseOral150 mg/1
Capsule, extended releaseOral200 mg/1
TabletOral200 1/1
TabletOral25 meq/1
Tablet, film coatedOral20 mg
TabletOral400 mg
Capsule, coatedOral50 mg
Capsule, coatedOral15 mg
Capsule, coatedOral25 mg
CapsuleOral
CapsuleOral15 mg
Capsule, coated pelletsOral15 mg/1
Capsule, coated pelletsOral25 mg/1
Capsule, gelatin coatedOral15 mg
Capsule, gelatin coatedOral25 mg
Capsule, gelatin coatedOral50 mg
TabletOral
TabletOral50.000 mg
Tablet, film coatedOral300 MG
Tablet, film coatedOral400 MG
TabletOral100 mg
Capsule, coated pelletsOral15 mg
TabletOral200 mg
Capsule, coated pelletsOral25 mg
TabletOral25 mg
Capsule, coated pelletsOral50 mg
Tablet, coatedOral100 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral25 mg/1
Tablet, coatedOral50 mg/1
Tablet, film coatedOral200 mg
Tablet, film coatedOral50 mg
CapsuleOral15 mg/1
CapsuleOral25 mg/1
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral25 mg/1
Capsule, extended releaseOral50 mg/1
PowderNot applicable1 1/1kg
TabletOral100 mg/1
TabletOral200 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
Tablet, film coatedOral100.0 mg
TabletOral25.000 mg
Tablet, coatedOral100 mg
Tablet, coatedOral25 mg
Tablet, coatedOral50 mg
CapsuleOral25 mg
CapsuleOral50 mg
Prices
Unit descriptionCostUnit
Topiramate 200 mg tablet8.32USD tablet
Topamax 200 mg tablet7.68USD tablet
Topiramate 100 mg tablet7.11USD tablet
Topamax 100 mg tablet6.31USD tablet
Topamax 50 mg tablet5.96USD tablet
Topiramate 50 mg tablet5.21USD tablet
Topiramate 25 mg Sprinkle Capsule3.04USD capsule
Topiramate 25 mg tablet2.61USD tablet
Topiramate 99.7% powder2.59USD g
Topiramate 15 mg Sprinkle Capsule2.52USD capsule
Topamax 25 mg tablet2.46USD tablet
Co Topiramate 200 mg Tablet2.08USD tablet
Mylan-Topiramate 200 mg Tablet2.08USD tablet
Novo-Topiramate 200 mg Tablet2.08USD tablet
Phl-Topiramate 200 mg Tablet2.08USD tablet
Pms-Topiramate 200 mg Tablet2.08USD tablet
Ratio-Topiramate 200 mg Tablet2.08USD tablet
Sandoz Topiramate 200 mg Tablet2.08USD tablet
Topamax Sprinkle 25 mg Capsule1.35USD capsule
Sandoz Topiramate 100 mg Tablet1.31USD tablet
Co Topiramate 100 mg Tablet1.31USD tablet
Mylan-Topiramate 100 mg Tablet1.31USD tablet
Novo-Topiramate 100 mg Tablet1.31USD tablet
Phl-Topiramate 100 mg Tablet1.31USD tablet
Pms-Topiramate 100 mg Tablet1.31USD tablet
Ratio-Topiramate 100 mg Tablet1.31USD tablet
Topamax Sprinkle 15 mg Capsule1.29USD capsule
Pms-Topiramate 50 mg Tablet1.05USD tablet
Co Topiramate 25 mg Tablet0.69USD tablet
Mylan-Topiramate 25 mg Tablet0.69USD tablet
Novo-Topiramate 25 mg Tablet0.69USD tablet
Phl-Topiramate 25 mg Tablet0.69USD tablet
Pms-Topiramate 25 mg Tablet0.69USD tablet
Ratio-Topiramate 25 mg Tablet0.69USD tablet
Sandoz Topiramate 25 mg Tablet0.69USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2322644No2005-07-262019-03-01Canada flag
US5998380Yes1999-12-072016-04-13US flag
US6503884Yes2003-01-072016-04-13US flag
US7018983Yes2006-03-282016-04-13US flag
US7498311Yes2009-03-032016-04-13US flag
US7125560Yes2006-10-242019-09-01US flag
US6071537No2000-06-062017-06-23US flag
US8895057No2014-11-252028-06-09US flag
US7056890No2006-06-062020-06-14US flag
US7553818No2009-06-302020-06-14US flag
US7659256No2010-02-092020-06-14US flag
US7674776No2010-03-092020-06-14US flag
US8580299No2013-11-122029-06-14US flag
US9011906No2015-04-212028-06-09US flag
US9011905No2015-04-212028-06-09US flag
US8895058No2014-11-252028-06-09US flag
US8580298No2013-11-122029-05-15US flag
US9101545No2015-08-112033-03-19US flag
US8652527No2014-02-182033-03-19US flag
US8889190No2014-11-182033-03-19US flag
US8889191No2014-11-182027-11-16US flag
US8298580No2012-10-302027-11-16US flag
US8663683No2014-03-042027-11-16US flag
US8877248No2014-11-042027-11-16US flag
US8298576No2012-10-302028-04-04US flag
US8992989No2015-03-312027-11-16US flag
US9555005No2017-01-312033-03-19US flag
US9549940No2017-01-242027-11-16US flag
US9555004No2017-01-312027-11-16US flag
US9622983No2017-04-182027-11-16US flag
US10314790No2019-06-112027-11-16US flag
US10363224No2019-07-302033-03-19US flag
US11433046No2020-08-212040-08-21US flag
US11633374No2020-08-212040-08-21US flag
US11826343No2020-08-212040-08-21US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)123-125 ºChttps://www.chemicalbook.com/ChemicalProductProperty_US_CB7402630.aspx
boiling point (°C)438.7https://www.lookchem.com/Topiramate/
water solubility9.8 mg/mLhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020505s038s039,020844s032s034lbl.pdf
logP0.13http://foodb.ca/compounds/FDB023601
logS-1.7http://foodb.ca/compounds/FDB023601
pKa8.7http://foodb.ca/compounds/FDB023601
Predicted Properties
PropertyValueSource
Water Solubility6.8 mg/mLALOGPS
logP1.29ALOGPS
logP0.13Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.09Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area115.54 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity72.3 m3·mol-1Chemaxon
Polarizability32.4 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9955
Blood Brain Barrier+0.9382
Caco-2 permeable-0.6055
P-glycoprotein substrateNon-substrate0.7905
P-glycoprotein inhibitor INon-inhibitor0.5311
P-glycoprotein inhibitor IINon-inhibitor0.9479
Renal organic cation transporterNon-inhibitor0.9131
CYP450 2C9 substrateNon-substrate0.9479
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.542
CYP450 1A2 substrateNon-inhibitor0.6623
CYP450 2C9 inhibitorNon-inhibitor0.7259
CYP450 2D6 inhibitorNon-inhibitor0.8674
CYP450 2C19 inhibitorNon-inhibitor0.6539
CYP450 3A4 inhibitorNon-inhibitor0.8469
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7952
Ames testAMES toxic0.518
CarcinogenicityNon-carcinogens0.5578
BiodegradationNot ready biodegradable0.9803
Rat acute toxicity2.5682 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8882
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-003r-5893000000-57939ef42b569234ad29
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03di-0239000000-994a7b97e101c455a792
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-01q9-2960000000-a11a150bcada5055d2e9
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014i-0090000000-c1fa3d6ff15890fc1418
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0059000000-a6337903cab01edce60e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0239000000-994a7b97e101c455a792
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0019000000-70e4dbbc883d87b14845
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-0059000000-9c2cc7dc15fe04febae9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000x-0298000000-8c900384fa18ce54dc39
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9143000000-87a4694d92d19441ca70
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-5290000000-7ca2b1fd6a222ccff3fb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-057i-8690000000-0e196697183ac896c4e8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.8899278
predicted
DarkChem Lite v0.1.0
[M-H]-179.0720278
predicted
DarkChem Lite v0.1.0
[M-H]-180.0506278
predicted
DarkChem Lite v0.1.0
[M-H]-180.4344
predicted
DeepCCS 1.0 (2019)
[M+H]+179.0413278
predicted
DarkChem Lite v0.1.0
[M+H]+179.5417278
predicted
DarkChem Lite v0.1.0
[M+H]+179.8334278
predicted
DarkChem Lite v0.1.0
[M+H]+183.69444
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.0815278
predicted
DarkChem Lite v0.1.0
[M+Na]+180.0533278
predicted
DarkChem Lite v0.1.0
[M+Na]+191.19173
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Garnett WR: Clinical pharmacology of topiramate: a review. Epilepsia. 2000;41 Suppl 1:S61-5. [Article]
  2. Chung JY, Kim MW, Kim M: Efficacy of zonisamide in migraineurs with nonresponse to topiramate. Biomed Res Int. 2014;2014:891348. doi: 10.1155/2014/891348. Epub 2014 Jul 2. [Article]
  3. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...

Components:
References
  1. Coppola G, Capovilla G, Montagnini A, Romeo A, Spano M, Tortorella G, Veggiotti P, Viri M, Pascotto A: Topiramate as add-on drug in severe myoclonic epilepsy in infancy: an Italian multicenter open trial. Epilepsy Res. 2002 Mar;49(1):45-8. [Article]
  2. Ceulemans B, Boel M, Claes L, Dom L, Willekens H, Thiry P, Lagae L: Severe myoclonic epilepsy in infancy: toward an optimal treatment. J Child Neurol. 2004 Jul;19(7):516-21. [Article]
  3. Nieto Barrera M, Candau Fernandez Mensaque R, Nieto Jimenez M: [Severe myoclonic epilepsy in infancy (Dravet's syndrome). Its nosological characteristics and therapeutic aspects]. Rev Neurol. 2003 Jul 1-15;37(1):64-8. [Article]
  4. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated cation channel activity
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...

Components:
References
  1. Rogawski MA, Gryder D, Castaneda D, Yonekawa W, Banks MK, Lia H: GluR5 kainate receptors, seizures, and the amygdala. Ann N Y Acad Sci. 2003 Apr;985:150-62. [Article]
  2. Gryder DS, Rogawski MA: Selective antagonism of GluR5 kainate-receptor-mediated synaptic currents by topiramate in rat basolateral amygdala neurons. J Neurosci. 2003 Aug 6;23(18):7069-74. [Article]
  3. Kaminski RM, Banerjee M, Rogawski MA: Topiramate selectively protects against seizures induced by ATPA, a GluR5 kainate receptor agonist. Neuropharmacology. 2004 Jun;46(8):1097-104. [Article]
  4. Braga MF, Aroniadou-Anderjaska V, Li H, Rogawski MA: Topiramate reduces excitability in the basolateral amygdala by selectively inhibiting GluK1 (GluR5) kainate receptors on interneurons and positively modulating GABAA receptors on principal neurons. J Pharmacol Exp Ther. 2009 Aug;330(2):558-66. doi: 10.1124/jpet.109.153908. Epub 2009 May 5. [Article]
  5. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]
Details
4. Carbonic anhydrase 2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Maryanoff BE, McComsey DF, Costanzo MJ, Hochman C, Smith-Swintosky V, Shank RP: Comparison of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II by using topiramate as a structural platform. J Med Chem. 2005 Mar 24;48(6):1941-7. [Article]
  2. Ma L, Huang YG, Deng YC, Tian JY, Rao ZR, Che HL, Zhang HF, Zhao G: Topiramate reduced sweat secretion and aquaporin-5 expression in sweat glands of mice. Life Sci. 2007 Jun 6;80(26):2461-8. Epub 2007 Apr 29. [Article]
  3. Di Fiore A, Scozzafava A, Winum JY, Montero JL, Pedone C, Supuran CT, De Simone G: Carbonic anhydrase inhibitors: binding of an antiglaucoma glycosyl-sulfanilamide derivative to human isoform II and its consequences for the drug design of enzyme inhibitors incorporating sugar moieties. Bioorg Med Chem Lett. 2007 Mar 15;17(6):1726-31. Epub 2007 Jan 8. [Article]
  4. Casini A, Antel J, Abbate F, Scozzafava A, David S, Waldeck H, Schafer S, Supuran CT: Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorg Med Chem Lett. 2003 Mar 10;13(5):841-5. [Article]
  5. Winum JY, Scozzafava A, Montero JL, Supuran CT: Sulfamates and their therapeutic potential. Med Res Rev. 2005 Mar;25(2):186-228. [Article]
  6. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]
Details
5. Carbonic anhydrase 4
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina an...
Gene Name
CA4
Uniprot ID
P22748
Uniprot Name
Carbonic anhydrase 4
Molecular Weight
35032.075 Da
References
  1. Abbate F, Casini A, Owa T, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett. 2004 Jan 5;14(1):217-23. [Article]
  2. Dodgson SJ, Shank RP, Maryanoff BE: Topiramate as an inhibitor of carbonic anhydrase isoenzymes. Epilepsia. 2000;41 Suppl 1:S35-9. doi: 10.1111/j.1528-1157.2000.tb06047.x. [Article]
  3. Masereel B, Rolin S, Abbate F, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties. J Med Chem. 2002 Jan 17;45(2):312-20. [Article]
  4. Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 2004 Feb 26;47(5):1272-9. [Article]
  5. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...

Components:
References
  1. Mula M, Cavanna AE, Monaco F: Psychopharmacology of topiramate: from epilepsy to bipolar disorder. Neuropsychiatr Dis Treat. 2006 Dec;2(4):475-88. doi: 10.2147/nedt.2006.2.4.475. [Article]
  2. Genome JP, Topiramate [Link]
Details
7. Carbonic anhydrase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
References
  1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [Article]
  2. Dodgson SJ, Shank RP, Maryanoff BE: Topiramate as an inhibitor of carbonic anhydrase isoenzymes. Epilepsia. 2000;41 Suppl 1:S35-9. doi: 10.1111/j.1528-1157.2000.tb06047.x. [Article]
Details
8. Carbonic anhydrase 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA3
Uniprot ID
P07451
Uniprot Name
Carbonic anhydrase 3
Molecular Weight
29557.215 Da
References
  1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [Article]
  2. Lehmann WD, Neumann GK, Kessler KF, Jonatha WD: [Frequency of obstetrical operations and perinatal mortality before and after admission of continuous fetal monitoring (author's transl)]. Geburtshilfe Frauenheilkd. 1976 Mar;36(3):247-55. [Article]
  3. Dodgson SJ, Shank RP, Maryanoff BE: Topiramate as an inhibitor of carbonic anhydrase isoenzymes. Epilepsia. 2000;41 Suppl 1:S35-9. doi: 10.1111/j.1528-1157.2000.tb06047.x. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1E gives rise to R-type calcium currents. R-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by nickel, and partially by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to dihydropyridines (DHP), omega-conotoxin-GVIA (omega-CTx-GVIA), and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing alpha-1E subunit could be involved in the modulation of firing patterns of neurons which is important for information processing.
Specific Function
Calcium channel activity

Components:
References
  1. Wormuth C, Lundt A, Henseler C, Muller R, Broich K, Papazoglou A, Weiergraber M: Review: Cav2.3 R-type Voltage-Gated Ca(2+) Channels - Functional Implications in Convulsive and Non-convulsive Seizure Activity. Open Neurol J. 2016 Sep 30;10:99-126. doi: 10.2174/1874205X01610010099. eCollection 2016. [Article]
  2. Kuzmiski JB, Barr W, Zamponi GW, MacVicar BA: Topiramate inhibits the initiation of plateau potentials in CA1 neurons by depressing R-type calcium channels. Epilepsia. 2005 Apr;46(4):481-9. doi: 10.1111/j.0013-9580.2005.35304.x. [Article]
  3. Maryanoff BE: Phenotypic Assessment and the Discovery of Topiramate. ACS Med Chem Lett. 2016 Jun 13;7(7):662-5. doi: 10.1021/acsmedchemlett.6b00176. eCollection 2016 Jul 14. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Nallani SC, Glauser TA, Hariparsad N, Setchell K, Buckley DJ, Buckley AR, Desai PB: Dose-dependent induction of cytochrome P450 (CYP) 3A4 and activation of pregnane X receptor by topiramate. Epilepsia. 2003 Dec;44(12):1521-8. [Article]
  2. Benedetti MS: Enzyme induction and inhibition by new antiepileptic drugs: a review of human studies. Fundam Clin Pharmacol. 2000 Jul-Aug;14(4):301-19. doi: 10.1111/j.1472-8206.2000.tb00411.x. [Article]
  3. Topamax (Topiramate) FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Garnett WR: Clinical pharmacology of topiramate: a review. Epilepsia. 2000;41 Suppl 1:S61-5. [Article]
  2. Sachdeo RC, Sachdeo SK, Levy RH, Streeter AJ, Bishop FE, Kunze KL, Mather GG, Roskos LK, Shen DD, Thummel KE, Trager WF, Curtin CR, Doose DR, Gisclon LG, Bialer M: Topiramate and phenytoin pharmacokinetics during repetitive monotherapy and combination therapy to epileptic patients. Epilepsia. 2002 Jul;43(7):691-6. [Article]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Curator comments
Although topiramate binds to serum albumin, it is not highly bound.
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bialer M, Doose DR, Murthy B, Curtin C, Wang SS, Twyman RE, Schwabe S: Pharmacokinetic interactions of topiramate. Clin Pharmacokinet. 2004;43(12):763-80. doi: 10.2165/00003088-200443120-00001. [Article]
  2. FDA Approved Drug Products: Topamax (topiramate) for oral use [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Luna-Tortos C, Rambeck B, Jurgens UH, Loscher W: The antiepileptic drug topiramate is a substrate for human P-glycoprotein but not multidrug resistance proteins. Pharm Res. 2009 Nov;26(11):2464-70. doi: 10.1007/s11095-009-9961-8. [Article]
  2. Sills GJ, Kwan P, Butler E, de Lange EC, van den Berg DJ, Brodie MJ: P-glycoprotein-mediated efflux of antiepileptic drugs: preliminary studies in mdr1a knockout mice. Epilepsy Behav. 2002 Oct;3(5):427-432. doi: 10.1016/s1525-5050(02)00511-5. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Tau-protein kinase activity
Specific Function
Catalytic subunit of AMP-activated protein kinase (AMPK), an energy sensor protein kinase that plays a key role in regulating cellular energy metabolism. In response to reduction of intracellular A...

Components:
References
  1. Ha E, Yim SV, Jung KH, Yoon SH, Zheng LT, Kim MJ, Hong SJ, Choe BK, Baik HH, Chung JH, Kim JW: Topiramate stimulates glucose transport through AMP-activated protein kinase-mediated pathway in L6 skeletal muscle cells. Pharmacogenomics J. 2006 Sep-Oct;6(5):327-32. doi: 10.1038/sj.tpj.6500366. Epub 2006 Jan 17. [Article]
  2. Wilkes JJ, Nguyen MT, Bandyopadhyay GK, Nelson E, Olefsky JM: Topiramate treatment causes skeletal muscle insulin sensitization and increased Acrp30 secretion in high-fat-fed male Wistar rats. Am J Physiol Endocrinol Metab. 2005 Dec;289(6):E1015-22. doi: 10.1152/ajpendo.00169.2005. Epub 2005 Jul 19. [Article]
  3. Coomans CP, Geerling JJ, van den Berg SA, van Diepen HC, Garcia-Tardon N, Thomas A, Schroder-van der Elst JP, Ouwens DM, Pijl H, Rensen PC, Havekes LM, Guigas B, Romijn JA: The insulin sensitizing effect of topiramate involves KATP channel activation in the central nervous system. Br J Pharmacol. 2013 Oct;170(4):908-18. doi: 10.1111/bph.12338. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48