Compound Detail
CHEMBL220492
TOPIRAMATE 💊 Approved Drug
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💊 Approved Drug
CC1(C)O[C@@H]2[C@@H](CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@H]23)O1
Basic Information
| ChEMBL ID | CHEMBL220492 |
| Name | TOPIRAMATE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | KJADKKWYZYXHBB-XBWDGYHZSA-N |
| Therapeutic | ✓ Yes |
34
Targets
363
Activities
3
Assay Types
6
PK Parameters
20
Publications
22
Known Names
20
Indications
6
Mechanisms
Molecular Properties
339.4
MW (Da)
-0.40
ALogP
8
HBA
1
HBD
115.5
PSA (Ų)
0.74
QED
0
Ro5 Violations
3
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1996 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Carbonic anhydrase II inhibitor | INHIBITOR | Carbonic anhydrase 2 | ✓ | ✓ |
| Carbonic anhydrase IV inhibitor | INHIBITOR | Carbonic anhydrase 4 | ✓ | ✓ |
| Glutamate receptor ionotropic AMPA antagonist | ANTAGONIST | Glutamate receptor ionotropic AMPA | ✓ | ✓ |
| Glutamate receptor ionotropic kainate antagonist | ANTAGONIST | Glutamate receptor ionotropic kainate | ✓ | ✓ |
| GABA-A receptor; anion channel positive modulator | POSITIVE MODULATOR | GABA-A receptor; anion channel | ✓ | ✓ |
| Sodium channel alpha subunit blocker | BLOCKER | Sodium channel alpha subunit | ✓ | ✓ |
Indications
Epilepsy Lennox Gastaut Syndrome Migraine Disorders Seizures Alcoholism Alcoholism Anxiety Bipolar Disorder Bulimia Cocaine-Related Disorders Dementia Depressive Disorder Diabetes Mellitus, Type 2 Epilepsies, Partial Epilepsy, Tonic-Clonic Essential Tremor Gambling Headache Hyperlipidemias Hypertension
ATC Classification
N03AX11
topiramate
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS
Activity Summary
Ki 344 meas. best 9.06
IC50 15 meas. best 8.3
Kd 4 meas. best 7.86
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Carbonic anhydrase 7 CHEMBL2326 | Ki | 9.06 | 8.9024 | 0.9 | 21 |
| Carbonic anhydrase 2 CHEMBL205 | IC50 | 8.3 | 6.76 | 5.0 | 3 |
| Carbonic anhydrase 2 CHEMBL205 | Ki | 8.3 | 7.8524 | 5.0 | 83 |
| Carbonate dehydratase CHEMBL3745586 | Ki | 8.18 | 8.18 | 6.6 | 1 |
| Unchecked CHEMBL612545 | Ki | 8.18 | 6.5368 | 6.6 | 37 |
| Carbonic anhydrase 2 CHEMBL205 | Kd | 7.86 | 6.98 | 13.8 | 3 |
| Carbonic anhydrase V CHEMBL2111457 | Ki | 7.59 | 7.59 | 25.4 | 1 |
| Carbonic anhydrase 5A, mitochondrial CHEMBL4789 | Kd | 7.59 | 7.59 | 25.4 | 1 |
| Alpha carbonic anhydrase CHEMBL1075028 | Ki | 7.54 | 7.54 | 29.1 | 2 |
| Carbonic anhydrase 5B, mitochondrial CHEMBL3969 | Ki | 7.52 | 7.52 | 30.0 | 11 |
| Astrosclerin-3 CHEMBL1944499 | Ki | 7.42 | 7.42 | 38.0 | 1 |
| Carbonic anhydrase 6 CHEMBL3025 | Ki | 7.35 | 7.35 | 45.0 | 7 |
| Carbonic anhydrase 13 CHEMBL2186 | Ki | 7.33 | 7.33 | 47.0 | 4 |
| Carbonic anhydrase 13 CHEMBL3912 | Ki | 7.33 | 7.33 | 47.0 | 1 |
| Carbonic anhydrase 4 CHEMBL281 | Ki | 7.27 | 7.27 | 54.0 | 5 |
| Carbonic anhydrase 4 CHEMBL281 | IC50 | 7.27 | 7.27 | 54.0 | 1 |
| Carbonic anhydrase 1 CHEMBL261 | Ki | 7.25 | 6.6098 | 56.0 | 66 |
| Carbonic anhydrase 9 CHEMBL3594 | Ki | 7.24 | 6.8896 | 58.0 | 25 |
| Carbonic anhydrase 5A, mitochondrial CHEMBL4789 | Ki | 7.2 | 6.9692 | 63.0 | 13 |
| Carbonic anhydrase 15 CHEMBL5973 | Ki | 7.11 | 7.11 | 78.0 | 3 |
| Carbonic anhydrase CHEMBL5931 | Ki | 6.96 | 6.96 | 110.0 | 1 |
| Carbonic anhydrase CHEMBL6185 | Ki | 6.96 | 6.96 | 110.0 | 1 |
| Carbonic anhydrase CHEMBL3932 | Ki | 6.92 | 6.455 | 120.0 | 2 |
| Carbonic anhydrase CHEMBL4211 | Ki | 6.76 | 6.725 | 172.0 | 2 |
| Carbonic anhydrase 1 CHEMBL261 | IC50 | 6.6 | 6.6 | 250.0 | 1 |
| Carbonic anhydrase CHEMBL1649055 | Ki | 6.43 | 6.43 | 367.0 | 1 |
| Carbonic anhydrase 2 CHEMBL1697676 | Ki | 6.43 | 6.43 | 367.0 | 2 |
| Delta carbonic anhydrase CHEMBL3097982 | Ki | 6.41 | 6.41 | 392.0 | 1 |
| Carbonic anhydrase 2 CHEMBL6068 | Ki | 6.32 | 6.32 | 474.0 | 1 |
| Beta-carbonic anhydrase 1 CHEMBL5631 | Ki | 6.21 | 6.21 | 610.0 | 2 |
| Carbonic anhydrase, alpha family CHEMBL3621035 | Ki | 6.11 | 6.11 | 769.0 | 1 |
| Carbonic anhydrase CHEMBL5337 | Ki | 5.96 | 5.96 | 1108.0 | 3 |
| Unchecked CHEMBL612545 | IC50 | 5.87 | 5.2443 | 1360.0 | 7 |
| Carbonic anhydrase 2 CHEMBL4706 | IC50 | 5.85 | 5.85 | 1400.0 | 1 |
| Carbonic anhydrase 14 CHEMBL3510 | Ki | 5.84 | 5.84 | 1460.0 | 12 |
| PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) CHEMBL5767 | Ki | 5.52 | 5.52 | 3020.0 | 1 |
| Carbonic anhydrase 12 CHEMBL3242 | Ki | 5.42 | 5.2667 | 3800.0 | 3 |
| Carbonic anhydrase 4 CHEMBL3729 | Ki | 5.31 | 5.31 | 4900.0 | 9 |
| Carbonic anhydrase CHEMBL3926 | Ki | 4.63 | 4.63 | 23500.0 | 1 |
| Sodium channel protein type 2 subunit alpha CHEMBL3399 | IC50 | 4.01 | 4.01 | 97000.0 | 2 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| F | 70.0 | % | Homo sapiens |
| F | 80.0 | % | Homo sapiens |
| Fu | 0.79 | - | Rattus norvegicus |
| Fu | 0.61 | - | Rattus norvegicus |
| T1/2 | 21.0 | hr | Homo sapiens |
| Vd | 3.2 | L.kg-1 | Rattus norvegicus |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 16472241 | 10.2174/1570163043334794 | Hepatotoxicity | 18 |
| 19388676 | 10.1021/jm801432r | Mus musculus | 14 |
| 22194678 | 10.1371/journal.pcbi.1002310 | Hepatotoxicity | 14 |
| 3572976 | 10.1021/jm00388a023 | Mus musculus | 13 |
| 15646539 | 10.1016/s0399-8320(04)95062-2 | Unchecked | 11 |
| 9548821 | 10.1021/jm970790w | Rattus norvegicus | 8 |
| 9548821 | 10.1021/jm970790w | Mus musculus | 8 |
| 21332115 | 10.1021/jm1013242 | Unchecked | 8 |
| 15646539 | 10.1016/s0399-8320(04)95062-2 | NON-PROTEIN TARGET | 8 |
| 18572411 | 10.1016/j.bmc.2008.06.005 | Aquaporin-4 | 7 |
| 18363349 | 10.1021/jm7015649 | Carbonic anhydrase 2 | 6 |
| 15771438 | 10.1021/jm040124c | Carbonic anhydrase 2 | 5 |
| 19388676 | 10.1021/jm801432r | Rattus norvegicus | 5 |
| 9548821 | 10.1021/jm970790w | Unchecked | 5 |
| 17646100 | 10.1016/j.bmcl.2007.07.019 | Unchecked | 4 |
| 21314129 | 10.1021/jm101525j | Unchecked | 4 |
| 9548821 | 10.1021/jm970790w | No relevant target | 4 |
| 11784136 | 10.1021/jm0109199 | Mus musculus | 4 |
| 19764786 | 10.1021/jm901036q | Plasma | 4 |
| 20201556 | 10.1021/jm901888x | Unchecked | 4 |
Data from ChEMBL 36 via Core Engine