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Topiramate

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Also known as (-)-topiramateEpitomaEpitomaxEprontiaMCN-4853QudexyQudexy xrRWJ-17021SincronilTopamacTopamaxTopamax sprinkleTopimaxTopinaTopiramate component of qsymiaTopiramatoTopomaxTrokendi xrUSL-255

Summary

Topiramate (CHEMBL220492) is an approved small-molecule anticonvulsant (ATC N03AX11) targeting CA1, CA4, and CA12; indicated across 48 conditions including epilepsy and visual epilepsy.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N03AX11
  • Targets: 4 (CA1, CA4, CA12…)
  • Indications: 48 conditions
  • Clinical trials: 230
  • Chemistry: 339.36 Da · C12H21NO8S

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL220492
NameTopiramate
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID5284627
ChEBICHEBI:63631
ATCN03AX11
Molecular formulaC12H21NO8S
Molecular weight339.36
InChIKeyKJADKKWYZYXHBB-XBWDGYHZSA-N

SMILES: CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C

IUPAC name: [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl sulfamate

ChEBI definition: A hexose derivative that is 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose in which the hydroxy group has been converted to the corresponding sulfamate ester. It blocks voltage-dependent sodium channels and is used as an antiepileptic and for the prevention of migraine.

Pharmacological roles (ChEBI): anticonvulsant, sodium channel blocker.

Also known as: (-)-topiramate, Epitoma, Epitomax, Eprontia, MCN-4853, Qudexy, Qudexy xr, RWJ-17021, Sincronil, Topamac, Topamax, Topamax sprinkle

Patent coverage: 9,527 distinct patent families (35,160 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CA1carbonic anhydrase 1Inhibition6.60%P00915
CA4carbonic anhydrase 4Inhibition7.370.3%P22748
CA12carbonic anhydrase 12Inhibition8.420.2%O43570
CA7carbonic anhydrase 7Inhibition9.051.6%P43166

Broader ChEMBL bioactivity targets: 23 (assay-derived). Sample: Carbonic anhydrase 2, Carbonic anhydrase V, Carbonic anhydrase 13, Carbonic anhydrase 7, Carbonic anhydrase 1, Carbonic anhydrase 4, Carbonic anhydrase 6, Carbonic anhydrase 12, Sodium channel protein type 2 subunit alpha, Carbonic anhydrase 14.

Bioactivity

ChEMBL activities: 285 potent at pChembl ≥ 5 of 290 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
CA79.06Ki0.87nMCHEMBL_ACT_1435974
CA79.06Ki0.87nMCHEMBL_ACT_2619678
CA79.05Ki0.9nMCHEMBL_ACT_10950742
CA79.05Ki0.9nMCHEMBL_ACT_13407598
CA79.05Ki0.9nMCHEMBL_ACT_13440683
CA79.05Ki0.9nMCHEMBL_ACT_13859515
CA79.05Ki0.9nMCHEMBL_ACT_1780679
CA79.05Ki0.9nMCHEMBL_ACT_18043977
CA79.05Ki0.9nMCHEMBL_ACT_18952624
CA79.05Ki0.9nMCHEMBL_ACT_1954043
CA79.05Ki0.9nMCHEMBL_ACT_2056568
CA79.05Ki0.9nMCHEMBL_ACT_23169524
CA79.05Ki0.9nMCHEMBL_ACT_25513757
CA79.05Ki0.9nMCHEMBL_ACT_2564675
CA79.05Ki0.9nMCHEMBL_ACT_29315986
CA79.05Ki0.9nMCHEMBL_ACT_2949481
CA79.05Ki0.9nMCHEMBL_ACT_3310916
CA79.05Ki0.9nMCHEMBL_ACT_6168790
CA79.05Ki0.9nMCHEMBL_ACT_6223163
CA79.05Ki0.9nMCHEMBL_ACT_6227541
CA28.3Ki5nMCHEMBL_ACT_1435973
CA28.3Ki5nMCHEMBL_ACT_1437691
CA28.3Ki5nMCHEMBL_ACT_1439693
CA28.3Ki5nMCHEMBL_ACT_145891
CA28.3Ki5nMCHEMBL_ACT_1606307
CA28.3Ki5nMCHEMBL_ACT_2939246
CA28.3Ki5nMCHEMBL_ACT_3256657
CA28.3Ki5nMCHEMBL_ACT_5303371
CA28.3Ki5nMCHEMBL_ACT_533960
CA28.3Ki5nMCHEMBL_ACT_591519

Target pathways

Aggregated over 4 target gene(s): CA1, CA4, CA12, CA7.

Top Reactome pathways

12 total, by targets touching each:

PathwayTargetsGenes
Metabolism4CA1, CA12, CA4, CA7
Reversible hydration of carbon dioxide4CA1, CA12, CA4, CA7
Erythrocytes take up carbon dioxide and release oxygen2CA1, CA4
Erythrocytes take up oxygen and release carbon dioxide2CA1, CA4
O2/CO2 exchange in erythrocytes2CA1, CA4
Transport of small molecules2CA1, CA4
Cytokine Signaling in Immune system1CA1
Immune System1CA1
Interleukin-12 family signaling1CA1
Signaling by Interleukins1CA1
Gene and protein expression by JAK-STAT signaling after Interleukin-12 stimulation1CA1
Interleukin-12 signaling1CA1

Dominant GO biological processes

GO termTargets
response to fructose1
bicarbonate transport1
estrous cycle1
chloride ion homeostasis1
positive regulation of synaptic transmission, GABAergic1
obsolete positive regulation of cellular pH reduction1
regulation of intracellular pH1
neuron cellular homeostasis1
regulation of chloride transport1

Indications & clinical

Indications

48 indications (4 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
epilepsy4MONDO:0005027EFO:0000474
visual epilepsy4MONDO:0001386HP:0001250
migraine disorder4MONDO:0005277MONDO:0005277
Lennox-Gastaut syndrome4MONDO:0016532MONDO:0016532
cocaine dependence3MONDO:0005186EFO:0002610
pathological gambling3MONDO:0011662EFO:0004699
obesity disorder3MONDO:0011122EFO:0001073
nicotine dependence3MONDO:0008575EFO:0003768
obsessive-compulsive disorder3MONDO:0008114EFO:0004242
essential tremor3MONDO:0003233EFO:0003108
focal epilepsy3MONDO:0005384EFO:0004263
Tourette syndrome3MONDO:0007661EFO:0004895
anxiety3MONDO:0011918EFO:0005230
binge eating disorder3MONDO:0005582EFO:0005924
dementia3MONDO:0001627HP:0000726
hypertensive disorder3MONDO:0005044EFO:0000537
alcohol abuse3MONDO:0002046MONDO:0002046
metabolic syndrome X3MONDO:0011565EFO:0000195
hypertriglyceridemia3MONDO:0005347EFO:0004211
epilepsy with generalized tonic-clonic seizures3MONDO:0005754EFO:0007262
depressive disorder3MONDO:0002050MONDO:0002050
type 2 diabetes mellitus3MONDO:0005148MONDO:0005148
Prader-Willi syndrome3MONDO:0008300MONDO:0008300
hyperlipidemia3MONDO:0021187MONDO:0021187
bipolar disorder3MONDO:0004985MONDO:0004985
mood disorder3MONDO:0005371EFO:0004247
methamphetamine dependence2MONDO:0005419EFO:0004701
post-traumatic stress disorder2MONDO:0005146EFO:0001358
diabetes mellitus2MONDO:0005015EFO:0000400
sciatica2MONDO:0024333HP:0011868
cannabis dependence2MONDO:0005689EFO:0007191
brain ischemia2MONDO:0005299MONDO:0005299
Parkinson disease2MONDO:0005180MONDO:0005180
multiple sclerosis2MONDO:0005301MONDO:0005301
sudden sensorineural hearing loss2MONDO:0043373MONDO:0043373
congenital heart disease1MONDO:0005453EFO:0005207
liver disorder1MONDO:0005154EFO:0001421
bulimia nervosa1MONDO:0005452EFO:0005204
HIV infectious disease1MONDO:0005109EFO:0000180
eating disorder0MONDO:0005451EFO:0005203

8 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 230.

Phase distribution

PhaseTrials
PHASE362
PHASE453
PHASE247
Not specified31
PHASE120
PHASE2/PHASE39
PHASE1/PHASE24
EARLY_PHASE14

Top trials by phase / activity

NCTPhaseStatusTitle
NCT04748601PHASE4RECRUITINGQudexy XR for the Prevention of Migraine in Children 6 to 11 Years Old
NCT05582837PHASE4RECRUITINGTreatment of Meniere’s Disease With Migraine Medications
NCT05975580PHASE4RECRUITINGPharmacotherapy in Conjunction With Lifestyle Counseling for Management of Weight Regain After Bariatric Surgery
NCT06499116PHASE4NOT_YET_RECRUITINGComparison of the Effectiveness of First-line Preventive Treatment of Migraine in Primary Care
NCT06799169PHASE4ACTIVE_NOT_RECRUITINGManagement of Acute Tinnitus With Migraine Medications
NCT06972056PHASE4RECRUITINGComparative Effectiveness of Migraine Preventive Medications: The APT Comparison Study
NCT00153699PHASE4UNKNOWNRelationship Between Topiramate Use and Ocular Angle Status
NCT00154076PHASE4COMPLETEDA Multicenter Comparative Trial of Zonisamide and Topiramate as Initial Monotherapy in Untreated Epilepsies
NCT00182455PHASE4TERMINATEDEfficacy of Adding Topiramate to Current Treatment in Treatment-Resistant Generalized Social Phobia (GSP)
NCT00182520PHASE4COMPLETEDEfficacy of Adding Topiramate to Current Treatment in Refractory Obsessive Compulsive Disorder (OCD)
NCT00200941PHASE4COMPLETEDEfficacy and Safety Study of Topiramate to Treat Restless Legs Syndrome
NCT00203190PHASE4TERMINATEDA Double-Blind, Placebo-Controlled Study Examining the Use of Topiramate in the Treatment of Cluster Headache
NCT00203463PHASE4COMPLETEDTopiramate in the Treatment of Post Traumatic Stress Disorder (PTSD)
NCT00208130PHASE4COMPLETEDTopiramate in the Treatment of Posttraumatic Stress Disorder in Civilians
NCT00211744PHASE4COMPLETEDTopiramate Augmentation in the Treatment of Obsessive-Compulsive Disorder
NCT00212810PHASE4COMPLETEDEvaluation of the Effectiveness of Topiramate in Preventing the Transformation From Episodic Migraine to Chronic Daily Headache.
NCT00216567PHASE4COMPLETEDSafety and Efficacy of Topamax Versus Carbamazepine in Benign Rolandic Epilepsy
NCT00266604PHASE4COMPLETEDA Study to Evaluate the Dosing, Effectiveness and Safety of Topiramate for the Treatment of Epilepsy
NCT00286988PHASE4TERMINATEDTopiramate for the Prophylactic Treatment of Cyclic Vomiting Syndrome in Children
NCT00329407PHASE4COMPLETEDThe Effects of Topiramate on Alcohol Use in Alcohol Dependent Subjects
NCT00393978PHASE4COMPLETEDEfficacy Study of Quetiapine Plus Topiramate for Reducing Cannabis Consumption and Bipolar Mania
NCT00394095PHASE4COMPLETEDTopiramate vs. Placebo in Preventing Weight Gain in Bipolar Disorder Treated With Olanzapine
NCT00432549PHASE4UNKNOWNDetoxification and Treatment of Subjects With Medication Overuse Headache
NCT00550394PHASE4COMPLETEDEfficacy and Tolerability of Topiramate in Treatment of Bipolar Mania and Alcohol Use in Adolescents and Young Adults
NCT00572117PHASE4COMPLETEDAdjunctive Topiramate for Treatment of Alcohol Dependence in Patients With Bipolar Disorder
NCT00626925PHASE4COMPLETEDTopiramate Treatment of Problem Drinkers
NCT00725920PHASE4COMPLETEDPlacebo Controled Clinical Trial Using Topiramate To Treat Posttraumatic Stress Disorder (PTSD) Patients.
NCT00846495PHASE4COMPLETEDPilot Study to Compare Frovatriptan vs. Topiramate for Prevention of Migraine
NCT00855738PHASE4COMPLETEDA Prospective, Observational Study On The Effectiveness Of New Antiepileptic Drugs As First Bitherapy In The Daily Clinical Practice
NCT00862095PHASE4TERMINATEDMedical Therapies for Chronic Post-Traumatic Headaches
NCT00988481PHASE4WITHDRAWNTopiramate Augmentation in Bulimia Nervosa Partial Responders
NCT01060111PHASE4COMPLETEDAn Efficacy and Tolerability Study of Topiramate in Participants With Migraine
NCT01087736PHASE4COMPLETEDTopiramate Treatment of Alcohol Use Disorders in Veterans With Post Traumatic Stress Disorder (PTSD): A Pilot Controlled Trial of Augmentation Therapy
NCT01135602PHASE4UNKNOWNTopiramate for Hospitalized Patients With Alcoholism: a 12-week Study
NCT01229735PHASE4COMPLETEDLevetiracetam Versus Topiramate as Adjunctive Therapy to Evaluate Efficacy and Safety in Subjects With Refractory Partial Onset Seizures
NCT01627860PHASE4COMPLETEDFirst Add-on vs. Mono-therapy Study of Topiramate in Neuro-Surgical Patients
NCT01689649PHASE4COMPLETEDA Study to Assess Tolerability and Efficacy of Topiramate Monotherapy in Recently Diagnosed Patients With Epilepsy
NCT01700387PHASE4COMPLETEDA Study to Evaluate the Tolerability of Botox and Topiramate or Botox and Placebo and Effect on Cognitive Efficiency
NCT01749215PHASE4COMPLETEDA Controlled Trial of Topiramate Treatment for Alcohol Dependence in Veterans With PTSD
NCT01750268PHASE4COMPLETEDTopiramate Treatment of Hazardous and Harmful Alcohol Use in Veterans With TBI

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 6 clinical and 19 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

89 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
ACETAMINOPHENChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
ACETAZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
BORTEZOMIBChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
BRINZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
CELECOXIBChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
CHLORTHALIDONEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
COUMARINChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
DICHLORPHENAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
DOBUTAMINEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
DORZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
ETHOXZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
FAMOTIDINEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
FUROSEMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
IMATINIBChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
INDAPAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
LACOSAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
LEVETIRACETAMChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
MAFENIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
METHAZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
NILOTINIBChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
SALICYLIC ACIDChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
SULFANILAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
TRICHLORMETHIAZIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
TRIENTINEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
VALDECOXIBChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
VERALIPRIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
ZONISAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA4, CA7
CAFFEIC ACIDChEMBLPhase 3CA1, CA12, CA4, CA7
CURCUMINChEMBLPhase 3CA1, CA12, CA4, CA7
QUERCETINChEMBLPhase 3CA1, CA12, CA4, CA7
RESVERATROLChEMBLPhase 3CA1, CA12, CA4, CA7
SACCHARINChEMBLPhase 3CA1, CA12, CA4, CA7
SPERMIDINEChEMBLPhase 3CA1, CA12, CA4, CA7
COUMAPHOSChEMBLPhase 2CA1, CA12, CA4, CA7
ELLAGIC ACIDChEMBLPhase 2CA1, CA12, CA4, CA7
GALLIC ACIDChEMBLPhase 2CA1, CA12, CA4, CA7
IROSUSTATChEMBLPhase 2CA1, CA12, CA4, CA7
PCI-27483ChEMBLPhase 2CA1, CA12, CA4, CA7
SONEPIPRAZOLEChEMBLPhase 2CA1, CA12, CA4, CA7
HYDROQUINONEChEMBLPhase 4 (approved)CA1, CA12, CA4
PHENOLChEMBLPhase 4 (approved)CA1, CA12, CA4
PYRITHIONE ZINCChEMBLPhase 4 (approved)CA12, CA4, CA7
SULPIRIDEChEMBLPhase 4 (approved)CA1, CA12, CA7
P-TOLUENESULFONAMIDEChEMBLPhase 3CA1, CA12, CA7
THIMEROSALChEMBLPhase 3CA12, CA4, CA7
CARZENIDEChEMBLPhase 2CA1, CA12, CA7
DAIDZEINChEMBLPhase 2CA12, CA4, CA7
DITIOCARBChEMBLPhase 2CA1, CA12, CA4
INDISULAMChEMBLPhase 2CA1, CA12, CA7
ISOQUERCETINChEMBLPhase 2CA12, CA4, CA7
LUTEOLINChEMBLPhase 2CA12, CA4, CA7
SULFASUCCINAMIDEChEMBLPhase 2CA1, CA12, CA4
PAZOPANIBChEMBL + PubChemPhase 4 (approved)CA1, CA12
SODIUMChEMBLPhase 4 (approved)CA1, CA4
SULTHIAMEChEMBLPhase 4 (approved)CA1, CA7
PRITELIVIRChEMBLPhase 3CA1, CA12
BENZYLSULFAMIDEChEMBLPhase 2CA1, CA12
FLAVONEChEMBLPhase 2CA1, CA12
PROPAZOLAMIDEChEMBLPhase 2CA1, CA4
PUERARINChEMBLPhase 2CA12, CA7

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot