Topiramate

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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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Topiramate (DB00273)

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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

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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 Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Alcohol dependence		••• •••••			••••••
Adjunct therapy in management of	Epilepsy, primary generalized tonic-clonic seizures		••••••••••••			•••••••• •••••••• •••••••
Management of	Epilepsy, primary generalized tonic-clonic seizures		••••••••••••			•••••••• •••••••• •••••••
Adjunct therapy in management of	Lennox-gastaut syndrome		••••••••••••			•••••••• ••••••••• ••••••
Prophylaxis of	Migraine		••••••••••••			•••••••• •••••••• •••••••

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Associated Therapies

• Chronic Weight Management therapy
• Weight Reduction

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

Target	Actions	Organism
AGlutamate receptor ionotropic, kainate 1	antagonist	Humans
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

• Topiramate
  • 2,3-Desisopropylidene Topiramate
  • 10-hydroxy topiramate
  • 9-hydroxy topiramate
  • 4,5-Desisopropylidene topiramate

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of CNS depression can be increased when Topiramate is combined with 1,2-Benzodiazepine.
Abacavir	Topiramate may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abemaciclib	The metabolism of Abemaciclib can be increased when combined with Topiramate.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Topiramate.
Acalabrutinib	The 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

Ingredient	UNII	CAS	InChI Key
Topiramate calcium	P956SY6RA6	1246279-00-4	VNRLRDKZOMPUAG-RZTSBURASA-N
Topiramate potassium	SMU8E1YBZ3	488127-51-1	VEKVPJSPZRTTGR-WGAVTJJLSA-N
Topiramate sodium	N808MSN0PT	488127-49-7	ZUWVVMMRNQEJMW-WGAVTJJLSA-N

Product Images

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Eprontia	Solution	25 mg/1mL	Oral	Azurity Pharmaceuticals, Inc.	2021-12-06	Not applicable
Gln-topiramate	Tablet	200 mg	Oral	Glenmark Pharmaceuticals, Inc	Not applicable	Not applicable
Gln-topiramate	Tablet	100 mg	Oral	Glenmark Pharmaceuticals, Inc	2007-07-12	Not applicable
Gln-topiramate	Tablet	100 mg	Oral	Glenmark Pharmaceuticals, Inc	Not applicable	Not applicable
Gln-topiramate	Tablet	25 mg	Oral	Glenmark Pharmaceuticals, Inc	2007-07-12	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Abbott-topiramate	Tablet	25 mg	Oral	Bgp Pharma Ulc	2014-03-12	2015-12-31
Abbott-topiramate	Tablet	200 mg	Oral	Bgp Pharma Ulc	2014-03-17	2015-12-31
Abbott-topiramate	Tablet	100 mg	Oral	Bgp Pharma Ulc	2014-03-12	2015-12-31
Accel-topiramate	Tablet	25 mg	Oral	Accel Pharma Inc	2015-03-26	2017-01-27
Accel-topiramate	Tablet	200 mg	Oral	Accel Pharma Inc	2015-03-26	2017-01-27

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Qsymia	Topiramate (23 mg/1) + Phentermine hydrochloride (3.75 mg/1)	Capsule, extended release	Oral	VIVUS LLC	2012-09-17	Not applicable
Qsymia	Topiramate (69 mg/1) + Phentermine hydrochloride (11.25 mg/1)	Capsule, extended release	Oral	VIVUS LLC	2012-09-17	Not applicable
Qsymia	Topiramate (92 mg/1) + Phentermine hydrochloride (15 mg/1)	Capsule, extended release	Oral	VIVUS LLC	2012-09-17	Not applicable
Qsymia	Topiramate (46 mg/1) + Phentermine hydrochloride (7.5 mg/1)	Capsule, extended release	Oral	VIVUS LLC	2012-09-17	Not applicable

Categories

ATC Codes

A08AA51 — Phentermine and topiramate

• A08AA — Centrally acting antiobesity products
• A08A — ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
• A08 — ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
• A — ALIMENTARY TRACT AND METABOLISM

N03AX11 — Topiramate

• N03AX — Other antiepileptics
• N03A — ANTIEPILEPTICS
• N03 — ANTIEPILEPTICS
• N — NERVOUS SYSTEM

Drug Categories

• Alimentary Tract and Metabolism
• Anti-Obesity Agents
• Anticonvulsants
• Antiobesity Preparations, Excl. Diet Products
• Carbohydrates
• Central Nervous System Agents
• Central Nervous System Depressants
• Centrally Acting Antiobesity Products
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP3A Inducers
• Cytochrome P-450 CYP3A4 Inducers
• Cytochrome P-450 CYP3A4 Inducers (strength unknown)
• Cytochrome P-450 CYP3A4 Inducers (weak)
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Decreased Central Nervous System Disorganized Electrical Activity
• Drugs that are Mainly Renally Excreted
• Enzyme Inducing Antiepileptic Drugs
• Hexoses
• Ketoses
• Miscellaneous Anticonvulsants
• Monosaccharides
• Nervous System
• Neuroprotective Agents
• P-glycoprotein substrates

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]

External Links

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

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Not Available	Completed	Not Available	Arthritis / Gout Flares / Headache / Migraine / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Convulsions / Epilepsy / Osteopenia (Disorder) / Osteoporosis / Seizures	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Epilepsy	2	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Epilepsy / Seizures	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Epileptic seizure	1	somestatus	stop reason	just information to hide

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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

Form	Route	Strength
Tablet	Oral	100.0000 mg
Tablet, film coated	Oral
Solution	Oral	25 mg/1mL
Capsule	Oral	5.000 mg
Tablet	Oral	100.000 mg
Tablet, film coated	Oral	100 mg
Tablet, film coated	Oral	25 mg
Tablet	Oral	50 mg
Capsule, extended release	Oral
Capsule, extended release	Oral	150 mg/1
Capsule, extended release	Oral	200 mg/1
Tablet	Oral	200 1/1
Tablet	Oral	25 meq/1
Tablet, film coated	Oral	20 mg
Tablet	Oral	400 mg
Capsule, coated	Oral	50 mg
Capsule, coated	Oral	15 mg
Capsule, coated	Oral	25 mg
Capsule	Oral	15 mg
Capsule, coated pellets	Oral	15 mg/1
Capsule, coated pellets	Oral	25 mg/1
Capsule, gelatin coated	Oral	15 mg
Capsule, gelatin coated	Oral	25 mg
Capsule, gelatin coated	Oral	50 mg
Tablet	Oral	50.000 mg
Tablet, film coated	Oral	300 MG
Tablet, film coated	Oral	400 MG
Tablet	Oral	100 mg
Capsule, coated pellets	Oral	15 mg
Tablet	Oral	200 mg
Capsule, coated pellets	Oral	25 mg
Tablet	Oral	25 mg
Capsule, coated pellets	Oral	50 mg
Tablet, coated	Oral	100 mg/1
Tablet, coated	Oral	200 mg/1
Tablet, coated	Oral	25 mg/1
Tablet, coated	Oral	50 mg/1
Tablet, film coated	Oral	200 mg
Tablet, film coated	Oral	50 mg
Capsule	Oral	15 mg/1
Capsule	Oral	25 mg/1
Capsule, extended release	Oral	100 mg/1
Capsule, extended release	Oral	25 mg/1
Capsule, extended release	Oral	50 mg/1
Powder	Not applicable	1 1/1kg
Tablet	Oral	100 mg/1
Tablet	Oral	200 mg/1
Tablet	Oral	25 mg/1
Tablet	Oral	50 mg/1
Tablet, film coated	Oral	100 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet, film coated	Oral	25 mg/1
Tablet, film coated	Oral	50 mg/1
Capsule	Oral
Tablet, film coated	Oral	100.0 mg
Tablet	Oral	25.000 mg
Tablet, coated	Oral	100 mg
Tablet, coated	Oral	25 mg
Tablet, coated	Oral	50 mg
Capsule	Oral	25 mg
Capsule	Oral	50 mg

Prices

Unit description	Cost	Unit
Topiramate 200 mg tablet	8.32USD	tablet
Topamax 200 mg tablet	7.68USD	tablet
Topiramate 100 mg tablet	7.11USD	tablet
Topamax 100 mg tablet	6.31USD	tablet
Topamax 50 mg tablet	5.96USD	tablet
Topiramate 50 mg tablet	5.21USD	tablet
Topiramate 25 mg Sprinkle Capsule	3.04USD	capsule
Topiramate 25 mg tablet	2.61USD	tablet
Topiramate 99.7% powder	2.59USD	g
Topiramate 15 mg Sprinkle Capsule	2.52USD	capsule
Topamax 25 mg tablet	2.46USD	tablet
Co Topiramate 200 mg Tablet	2.08USD	tablet
Mylan-Topiramate 200 mg Tablet	2.08USD	tablet
Novo-Topiramate 200 mg Tablet	2.08USD	tablet
Phl-Topiramate 200 mg Tablet	2.08USD	tablet
Pms-Topiramate 200 mg Tablet	2.08USD	tablet
Ratio-Topiramate 200 mg Tablet	2.08USD	tablet
Sandoz Topiramate 200 mg Tablet	2.08USD	tablet
Topamax Sprinkle 25 mg Capsule	1.35USD	capsule
Sandoz Topiramate 100 mg Tablet	1.31USD	tablet
Co Topiramate 100 mg Tablet	1.31USD	tablet
Mylan-Topiramate 100 mg Tablet	1.31USD	tablet
Novo-Topiramate 100 mg Tablet	1.31USD	tablet
Phl-Topiramate 100 mg Tablet	1.31USD	tablet
Pms-Topiramate 100 mg Tablet	1.31USD	tablet
Ratio-Topiramate 100 mg Tablet	1.31USD	tablet
Topamax Sprinkle 15 mg Capsule	1.29USD	capsule
Pms-Topiramate 50 mg Tablet	1.05USD	tablet
Co Topiramate 25 mg Tablet	0.69USD	tablet
Mylan-Topiramate 25 mg Tablet	0.69USD	tablet
Novo-Topiramate 25 mg Tablet	0.69USD	tablet
Phl-Topiramate 25 mg Tablet	0.69USD	tablet
Pms-Topiramate 25 mg Tablet	0.69USD	tablet
Ratio-Topiramate 25 mg Tablet	0.69USD	tablet
Sandoz Topiramate 25 mg Tablet	0.69USD	tablet

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Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
CA2322644	No	2005-07-26	2019-03-01
US5998380	Yes	1999-12-07	2016-04-13
US6503884	Yes	2003-01-07	2016-04-13
US7018983	Yes	2006-03-28	2016-04-13
US7498311	Yes	2009-03-03	2016-04-13
US7125560	Yes	2006-10-24	2019-09-01
US6071537	No	2000-06-06	2017-06-23
US8895057	No	2014-11-25	2028-06-09
US7056890	No	2006-06-06	2020-06-14
US7553818	No	2009-06-30	2020-06-14
US7659256	No	2010-02-09	2020-06-14
US7674776	No	2010-03-09	2020-06-14
US8580299	No	2013-11-12	2029-06-14
US9011906	No	2015-04-21	2028-06-09
US9011905	No	2015-04-21	2028-06-09
US8895058	No	2014-11-25	2028-06-09
US8580298	No	2013-11-12	2029-05-15
US9101545	No	2015-08-11	2033-03-19
US8652527	No	2014-02-18	2033-03-19
US8889190	No	2014-11-18	2033-03-19
US8889191	No	2014-11-18	2027-11-16
US8298580	No	2012-10-30	2027-11-16
US8663683	No	2014-03-04	2027-11-16
US8877248	No	2014-11-04	2027-11-16
US8298576	No	2012-10-30	2028-04-04
US8992989	No	2015-03-31	2027-11-16
US9555005	No	2017-01-31	2033-03-19
US9549940	No	2017-01-24	2027-11-16
US9555004	No	2017-01-31	2027-11-16
US9622983	No	2017-04-18	2027-11-16
US10314790	No	2019-06-11	2027-11-16
US10363224	No	2019-07-30	2033-03-19
US11433046	No	2020-08-21	2040-08-21
US11633374	No	2020-08-21	2040-08-21
US11826343	No	2020-08-21	2040-08-21
US11911362	No	2020-08-21	2040-08-21

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	123-125 ºC	https://www.chemicalbook.com/ChemicalProductProperty_US_CB7402630.aspx
boiling point (°C)	438.7	https://www.lookchem.com/Topiramate/
water solubility	9.8 mg/mL	https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020505s038s039,020844s032s034lbl.pdf
logP	0.13	http://foodb.ca/compounds/FDB023601
logS	-1.7	http://foodb.ca/compounds/FDB023601
pKa	8.7	http://foodb.ca/compounds/FDB023601

Predicted Properties

Property	Value	Source
Water Solubility	6.8 mg/mL	ALOGPS
logP	1.29	ALOGPS
logP	0.13	Chemaxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.09	Chemaxon
pKa (Strongest Basic)	-3.7	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	115.54 Å2	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	72.3 m3·mol-1	Chemaxon
Polarizability	32.4 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9955
Blood Brain Barrier	+	0.9382
Caco-2 permeable	-	0.6055
P-glycoprotein substrate	Non-substrate	0.7905
P-glycoprotein inhibitor I	Non-inhibitor	0.5311
P-glycoprotein inhibitor II	Non-inhibitor	0.9479
Renal organic cation transporter	Non-inhibitor	0.9131
CYP450 2C9 substrate	Non-substrate	0.9479
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.542
CYP450 1A2 substrate	Non-inhibitor	0.6623
CYP450 2C9 inhibitor	Non-inhibitor	0.7259
CYP450 2D6 inhibitor	Non-inhibitor	0.8674
CYP450 2C19 inhibitor	Non-inhibitor	0.6539
CYP450 3A4 inhibitor	Non-inhibitor	0.8469
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7952
Ames test	AMES toxic	0.518
Carcinogenicity	Non-carcinogens	0.5578
Biodegradation	Not ready biodegradable	0.9803
Rat acute toxicity	2.5682 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8882
hERG inhibition (predictor II)	Non-inhibitor	0.8734

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-003r-5893000000-57939ef42b569234ad29
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-03di-0239000000-994a7b97e101c455a792
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-01q9-2960000000-a11a150bcada5055d2e9
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-014i-0090000000-c1fa3d6ff15890fc1418
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-00di-0059000000-a6337903cab01edce60e
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-0239000000-994a7b97e101c455a792
MS/MS Spectrum - , positive	LC-MS/MS	splash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0019000000-70e4dbbc883d87b14845
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-002r-0059000000-9c2cc7dc15fe04febae9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000x-0298000000-8c900384fa18ce54dc39
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9143000000-87a4694d92d19441ca70
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-5290000000-7ca2b1fd6a222ccff3fb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-057i-8690000000-0e196697183ac896c4e8
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[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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Details1. Glutamate receptor ionotropic, kainate 1

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

Ionotropic glutamate receptor that functions as a cation-permeable ligand-gated ion channel, gated by L-glutamate and the glutamatergic agonist kainic acid. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist

Specific Function

glutamate-gated calcium ion channel activity

Gene Name

GRIK1

Uniprot ID

P39086

Uniprot Name

Glutamate receptor ionotropic, kainate 1

Molecular Weight

103979.665 Da

References

1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. Gamma-aminobutyric acid receptor subunit alpha-1

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Alpha subunit of the heteropentameric ligand-gated chloride channel gated by Gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:23909897, PubMed:25489750, PubMed:29950725, PubMed:30602789). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (PubMed:29950725, PubMed:30602789). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:23909897, PubMed:29950725, PubMed:30602789). Alpha-1/GABRA1-containing GABAARs are largely synaptic (By similarity). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (By similarity). GABAARs containing alpha-1 and beta-2 or -3 subunits exhibit synaptogenic activity; the gamma-2 subunit being necessary but not sufficient to induce rapid synaptic contacts formation (PubMed:23909897, PubMed:25489750). GABAARs function also as histamine receptor where histamine binds at the interface of two neighboring beta subunits and potentiates GABA response (By similarity). GABAARs containing alpha, beta and epsilon subunits also permit spontaneous chloride channel activity while preserving the structural information required for GABA-gated openings (By similarity). Alpha-1-mediated plasticity in the orbitofrontal cortex regulates context-dependent action selection (By similarity). Together with rho subunits, may also control neuronal and glial GABAergic transmission in the cerebellum (By similarity)

Specific Function

GABA-A receptor activity

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]

Details3. Voltage-gated sodium channel alpha subunit (Protein Group)

Kind

Protein group

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General 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 sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:14672992). Plays a key role in brain, probably by regulating the moment when neurotransmitters are released in neurons. Involved in sensory perception of mechanical pain: activation in somatosensory neurons induces pain without neurogenic inflammation and produces hypersensitivity to mechanical, but not thermal stimuli

Specific Function

voltage-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential

---

Components:

Name	UniProt ID
Sodium channel protein type 1 subunit alpha	P35498
Sodium channel protein type 10 subunit alpha	Q9Y5Y9
Sodium channel protein type 11 subunit alpha	Q9UI33
Sodium channel protein type 2 subunit alpha	Q99250
Sodium channel protein type 3 subunit alpha	Q9NY46
Sodium channel protein type 4 subunit alpha	P35499
Sodium channel protein type 5 subunit alpha	Q14524
Sodium channel protein type 7 subunit alpha	Q01118
Sodium channel protein type 8 subunit alpha	Q9UQD0
Sodium channel protein type 9 subunit alpha	Q15858

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]

Details4. Kainate receptors (Protein Group)

Kind

Protein group

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

Ionotropic glutamate receptor that functions as a cation-permeable ligand-gated ion channel, gated by L-glutamate and the glutamatergic agonist kainic acid. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist

Specific Function

glutamate-gated calcium ion channel activity

---

Components:

Name	UniProt ID
Glutamate receptor ionotropic, kainate 1	P39086
Glutamate receptor ionotropic, kainate 2	Q13002
Glutamate receptor ionotropic, kainate 3	Q13003
Glutamate receptor ionotropic, kainate 4	Q16099
Glutamate receptor ionotropic, kainate 5	Q16478

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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	5	N/A	N/A	A27516
IC 50 (nM)	2100	N/A	N/A	A27553
Kd (nM)	290	N/A	N/A	A27550 / A27552
Kd (nM)	13.8	N/A	N/A	A27551
Ki (nM)	5	N/A	N/A	A10349 / A27514 / A10345 / A27515 / A10347 / A27519 / A27520 / A27532 / A27534 / A27540 / A27543
Ki (nM)	5	7.4	25	A10350
Ki (nM)	5000	N/A	N/A	A27517
Ki (nM)	9	N/A	N/A	A27518
Ki (nM)	500	N/A	N/A	A10342
Ki (nM)	7700	N/A	N/A	A10342
Ki (nM)	430	N/A	N/A	A10342
Ki (nM)	9600	N/A	N/A	A10342
Ki (nM)	10.3	N/A	N/A	A10942
Ki (nM)	5	7.5	22	A27548
Ki (nM)	10	7.5	25	A27549 / A27522
Ki (nM)	10	N/A	N/A	A27521 / A6377 / A27524 / A27525 / A27527 / A27528 / A27529 / A27530 / A27531 / A4564 / A27554 / A27533 / A27535 / A27536 / A27537 / A27538 / A27539 / A27541 / A27542 / A27545 / A27555 / A27556 / A27546 / A27547
Ki (nM)	10	7.5	22	A27523
Ki (nM)	450	N/A	N/A	A27552
Ki (nM)	10	7.4	25	A27526
Ki (nM)	300	N/A	N/A	A27553
Ki (nM)	10000	N/A	N/A	A27544

Details

Binding Properties5. Carbonic anhydrase 2

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Catalyzes the reversible hydration of carbon dioxide (PubMed:11327835, PubMed:11802772, PubMed:11831900, PubMed:12056894, PubMed:12171926, PubMed:1336460, PubMed:14736236, PubMed:15300855, PubMed:15453828, PubMed:15667203, PubMed:15865431, PubMed:16106378, PubMed:16214338, PubMed:16290146, PubMed:16686544, PubMed:16759856, PubMed:16807956, PubMed:17127057, PubMed:17251017, PubMed:17314045, PubMed:17330962, PubMed:17346964, PubMed:17540563, PubMed:17588751, PubMed:17705204, PubMed:18024029, PubMed:18162396, PubMed:18266323, PubMed:18374572, PubMed:18481843, PubMed:18618712, PubMed:18640037, PubMed:18942852, PubMed:1909891, PubMed:1910042, PubMed:19170619, PubMed:19186056, PubMed:19206230, PubMed:19520834, PubMed:19778001, PubMed:7761440, PubMed:7901850, PubMed:8218160, PubMed:8262987, PubMed:8399159, PubMed:8451242, PubMed:8485129, PubMed:8639494, PubMed:9265618, PubMed:9398308). Can also hydrate cyanamide to urea (PubMed:10550681, PubMed:11015219). Stimulates the chloride-bicarbonate exchange activity of SLC26A6 (PubMed:15990874). Essential for bone resorption and osteoclast differentiation (PubMed:15300855). Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption

Specific Function

arylesterase activity

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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	4900	N/A	N/A	A27520 / A27524 / A27525 / A27528 / A27533 / A27535
Ki (nM)	4900	7.5	22	A27523
Ki (nM)	4900	7.4	25	A27526

Details

Binding Properties6. Carbonic anhydrase 4

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Catalyzes the reversible hydration of carbon dioxide into bicarbonate and protons and thus is essential to maintaining intracellular and extracellular pH (PubMed:15563508, PubMed:16686544, PubMed:16807956, PubMed:17127057, PubMed:17314045, PubMed:17652713, PubMed:17705204, PubMed:18618712, PubMed:19186056, PubMed:19206230, PubMed:7625839). May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis (PubMed:15563508). It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid (PubMed:15563508)

Specific Function

carbonate dehydratase activity

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]

Details7. Voltage gated L-type calcium channel (Protein Group)

Kind

Protein group

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

Pore-forming, alpha-1C subunit of the voltage-gated calcium channel that gives rise to L-type calcium currents (PubMed:11741969, PubMed:12176756, PubMed:12181424, PubMed:15454078, PubMed:15863612, PubMed:16299511, PubMed:17071743, PubMed:17224476, PubMed:20953164, PubMed:23677916, PubMed:24728418, PubMed:26253506, PubMed:27218670, PubMed:29078335, PubMed:29742403, PubMed:30023270, PubMed:30172029, PubMed:34163037, PubMed:7737988, PubMed:8099908, PubMed:8392192, PubMed:9013606, PubMed:9087614, PubMed:9607315). Mediates influx of calcium ions into the cytoplasm, and thereby triggers calcium release from the sarcoplasm (By similarity). Plays an important role in excitation-contraction coupling in the heart. Required for normal heart development and normal regulation of heart rhythm (PubMed:15454078, PubMed:15863612, PubMed:17224476, PubMed:24728418, PubMed:26253506). Required for normal contraction of smooth muscle cells in blood vessels and in the intestine. Essential for normal blood pressure regulation via its role in the contraction of arterial smooth muscle cells (PubMed:28119464). Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group (Probable)

Specific Function

alpha-actinin binding

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Components:

Name	UniProt ID
Voltage-dependent L-type calcium channel subunit alpha-1C	Q13936
Voltage-dependent L-type calcium channel subunit alpha-1D	Q01668
Voltage-dependent L-type calcium channel subunit alpha-1F	O60840
Voltage-dependent L-type calcium channel subunit alpha-1S	Q13698
Voltage-dependent L-type calcium channel subunit beta-1	Q02641
Voltage-dependent L-type calcium channel subunit beta-2	Q08289
Voltage-dependent L-type calcium channel subunit beta-3	P54284
Voltage-dependent L-type calcium channel subunit beta-4	O00305

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]

Binding Properties

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	250	N/A	N/A	A27516
Ki (nM)	250	N/A	N/A	A10349 / A27514 / A10345 / A27515 / A10347 / A27517 / A27519 / A27520 / A27521 / A6377 / A27524 / A27525 / A27527 / A27528 / A27529 / A27530 / A27531 / A4564 / A27532 / A27533 / A27534 / A27535 / A27536 / A27537 / A27538 / A27539 / A27540 / A27541 / A27542 / A27543 / A27545 / A27546 / A27547
Ki (nM)	250	7.4	25	A10350 / A27526
Ki (nM)	15	N/A	N/A	A27518
Ki (nM)	250	7.5	25	A27522
Ki (nM)	250	7.5	22	A27523
Ki (nM)	250000	N/A	N/A	A27544

Details

Binding Properties8. Carbonic anhydrase 1

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

Catalyzes the reversible hydration of carbon dioxide (PubMed:10550681, PubMed:16506782, PubMed:16686544, PubMed:16807956, PubMed:17127057, PubMed:17314045, PubMed:17407288, PubMed:18618712, PubMed:19186056, PubMed:19206230). Can hydrate cyanamide to urea (PubMed:10550681)

Specific Function

arylesterase activity

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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	780000	N/A	N/A	A20066 / A27533 / A27535
Ki (nM)	780000	7.4	25	A27526

Details

Binding Properties9. Carbonic anhydrase 3

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

Reversible hydration of carbon dioxide

Specific Function

carbonate dehydratase activity

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]

Details10. Voltage-dependent R-type calcium channel (Protein Group)

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 (PubMed:30343943). They 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. They are however insensitive to dihydropyridines (DHP). 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 ion binding

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Components:

Name	UniProt ID
Voltage-dependent R-type calcium channel subunit alpha-1E	Q15878

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]

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Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 13:58