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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL220492
CHEMBL220492
Compound Name TOPIRAMATE
ChEMBL Synonyms EPITOMAX | MCN-4853 | TOPAMAX | RWJ-17021 | TOPIRAMATE | QUDEXY XR | TROKENDI XR | TOPAMAX SPRINKLE
Max Phase 4 (Approved)
Trade Names EPITOMAX | TOPAMAX | TOPAMAX SPRINKLE | QUDEXY XR | TROKENDI XR | TOPIRAMATE
Molecular Formula C12H21NO8S

Additional synonyms for CHEMBL220492 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N)OC(C)(C)O[C@H]3[C@@H]2O1
Standard InChI InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9( ...
Download InChI
Standard InChI Key KJADKKWYZYXHBB-XBWDGYHZSA-N

Sources

  • British National Formulary
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL220492

Molecule Features

CHEMBL220492 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Carbonic anhydrase II inhibitor Carbonic anhydrase II DailyMed PubMed
Carbonic anhydrase IV inhibitor Carbonic anhydrase IV DailyMed PubMed
GABA-A receptor; anion channel positive modulator GABA-A receptor; anion channel DailyMed PubMed
Glutamate receptor ionotropic AMPA antagonist Glutamate receptor ionotropic AMPA DailyMed PubMed
Glutamate receptor ionotropic kainate antagonist Glutamate receptor ionotropic kainate DailyMed PubMed
Sodium channel alpha subunit blocker Sodium channel alpha subunit DailyMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Multiple SclerosisD009103EFO:0003885multiple sclerosis2ClinicalTrials
Tobacco Use DisorderD014029EFO:0003768nicotine dependence3ClinicalTrials
Feeding and Eating DisordersD001068EFO:0005203eating disorder0ClinicalTrials
Marijuana AbuseD002189EFO:0004218marijuana dependence2ClinicalTrials
Peripheral Nervous System DiseasesD010523EFO:0003100peripheral neuropathy2ClinicalTrials
Epilepsies, PartialD004828EFO:0004263partial epilepsy2ClinicalTrials
EpilepsyD004827EFO:0000474epilepsy4ATC
ClinicalTrials
SciaticaD012585HP:0011868Sciatica2ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence3ClinicalTrials
Obsessive-Compulsive DisorderD009771EFO:0004242obsessive-compulsive disorder3ClinicalTrials
Parkinson DiseaseD010300EFO:0002508Parkinson's disease2ClinicalTrials
Smoking CessationD016540EFO:0004319smoking cessation3ClinicalTrials
Stress Disorders, Post-TraumaticD013313EFO:0001358post-traumatic stress disorder2ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
Bulimia NervosaD052018EFO:0005204bulimia nervosa1ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression3ClinicalTrials
Essential TremorD020329EFO:0003108essential tremor3ClinicalTrials
Hernias, Diaphragmatic, CongenitalD065630EFO:0005207congenital heart disease1ClinicalTrials
Lennox Gastaut SyndromeD065768Orphanet:2382Lennox-Gastaut syndrome3ClinicalTrials
Alcohol DrinkingD000428EFO:0004329alcohol drinking2ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence3ClinicalTrials
DementiaD003704HP:0000726dementia3ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus2ClinicalTrials
GamblingD005715EFO:0004699gambling behaviour2ClinicalTrials
Liver DiseasesD008107EFO:0001421liver disease1ClinicalTrials
ObesityD009765EFO:0001073obesity3ClinicalTrials
Prader-Willi SyndromeD011218Orphanet:739Prader-Willi syndrome3ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
Amphetamine-Related DisordersD019969EFO:0004701metamphetamine dependence2ClinicalTrials
Brain IschemiaD002545HP:0002637Cerebral ischemia2ClinicalTrials
BulimiaD002032EFO:0005924binge eating3ClinicalTrials
Cognitive DysfunctionD060825HP:0100543cognitive impairment1ClinicalTrials
Tourette SyndromeD005879EFO:0004895Tourette syndrome3ClinicalTrials
Bipolar DisorderD001714EFO:0000289bipolar disorder3ClinicalTrials
HeadacheD006261HP:0002315Headache2ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder3ClinicalTrials
SeizuresD012640HP:0001250Seizures2ClinicalTrials

Clinical Data

ClinicalTrials.gov TOPIRAMATE
The Cochrane Collaboration TOPIRAMATE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL220492. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 1.000
CHEMBL2186 Carbonic anhydrase XIII Mus musculus 1.000
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 1.000
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 1.000
CHEMBL5973 Carbonic anhydrase 15 Mus musculus 1.000
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 1.000
CHEMBL5931 Carbonic anhydrase Saccharomyces cerevisiae S288c 1.000
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 1.000
CHEMBL4211 Carbonic anhydrase 1 Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori) 1.000
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.999
CHEMBL5631 Uncharacterized protein Rv1284/MT1322 Mycobacterium tuberculosis 0.987
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.963
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 0.795
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.314
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.288



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 1.000
CHEMBL2186 Carbonic anhydrase XIII Mus musculus 1.000
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 1.000
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 1.000
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 1.000
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 1.000
CHEMBL5973 Carbonic anhydrase 15 Mus musculus 1.000
CHEMBL5931 Carbonic anhydrase Saccharomyces cerevisiae S288c 1.000
CHEMBL4211 Carbonic anhydrase 1 Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori) 1.000
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.995
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.969
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 0.943
CHEMBL5767 PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) Mycobacterium tuberculosis 0.866
CHEMBL5631 Uncharacterized protein Rv1284/MT1322 Mycobacterium tuberculosis 0.838
CHEMBL2885 Carbonic anhydrase III Homo sapiens 0.661
CHEMBL3912 Carbonic anhydrase XIII Homo sapiens 0.601
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.363

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
339.4 339.0988 -0.4 3 115.54 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
8 1 0 9 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.22 - 2.16 2.15 0 22 0.74

Structural Alerts

There are 5 structural alerts for CHEMBL220492. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N03 - ANTIEPILEPTICS
N03A - ANTIEPILEPTICS
N03AX - Other antiepileptics
N03AX11 - topiramate

ChemSpider ChemSpider:KJADKKWYZYXHBB-XBWDGYHZSA-N
DailyMed topiramate
PubChem SID: 144205025 SID: 144212718 SID: 170464746
Wikipedia Topiramate

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL220492



ACToR 97240-79-4
Atlas topiramate
BindingDB 10887
Brenda 191445 166019
ChEBI 63631
ChemicalBook CB7402630
DrugBank DB00273
DrugCentral 2706
eMolecules 594585 29547217 29548990
EPA CompTox Dashboard DTXSID8023688
FDA SRS 0H73WJJ391
Guide to Pharmacology 6849
Human Metabolome Database HMDB0005034
IBM Patent System 7DC1ADBFF572BD87DDA24A9011D9E812
KEGG Ligand C07502
LINCS LSM-5435
Mcule MCULE-9403222429
MolPort MolPort-001-615-062
NIH Clinical Collection SAM001246601
Nikkaji J345.989F
PDBe TOR
PharmGKB PA451728
PubChem 5284627
PubChem: Drugs of the Future 12013555
PubChem: Thomson Pharma 14924784 14777895
Selleck Topiramate
SureChEMBL SCHEMBL34631
ZINC ZINC000095616603

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/KJADKKWYZYXHBB-XBWDGYHZSA-N spacer
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