Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H20NO8S.Na |
| Molecular Weight | 361.344 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC1(C)O[C@@H]2CO[C@@]3(COS([NH-])(=O)=O)OC(C)(C)O[C@H]3[C@@H]2O1
InChI
InChIKey=ZUWVVMMRNQEJMW-WGAVTJJLSA-N
InChI=1S/C12H20NO8S.Na/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,(H-,13,14,15);/q-1;+1/t7-,8-,9+,12+;/m1./s1
| Molecular Formula | C12H21NO8S |
| Molecular Weight | 339.362 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00273Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020505s055,020844s046lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00273
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020505s055,020844s046lbl.pdf
Topiramate is an anticonvulsant indicated in the treatment of epilepsy and migraine. Topiramate enhances GABA-activated chloride channels. In addition, topiramate inhibits excitatory neurotransmission, through actions on kainate and AMPA receptors. There is evidence that topiramate has a specific effect on GluR5 kainate receptors. It is also an inhibitor of carbonic anhydrase, particular subtypes II and IV, but this action is weak and unlikely to be related to its anticonvulsant actions, but may account for the bad taste and the development of renal stones seen during treatment. Its possible effect as a mood stabilizer seems to occur before anticonvulsant qualities at lower dosages. Topiramate inhibits maximal electroshock and pentylenetetrazol-induced seizures as well as partial and secundarily generalized tonic-clonic seizures in the kindling model, findings predective of a broad spectrum of antiseizure activities clinically. The precise mechanism of action of topiramate is not known. However, studies have shown that topiramate blocks the action potentials elicited repetitively by a sustained depolarization of the neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Topiramate also augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAAreceptor (controls an integral chloride channel), indicating a possible mechanism through potentiation of the activity of GABA. Topiramate also demonstrates antagonism of the AMPA/kainate subtype of the glutamate excitatory amino acid receptor. It also inhibits carbonic anhydrase (particularly isozymes II and IV), but this action is weak and unlikely to be related to its anticonvulsant actions. Topiramate is used for the treatment and control of partial seizures and severe tonic-clonic (grand mal) seizures and also for the prevention of migraine headaches. In children it is also used for treatment of Lennox-Gastaut syndrome. Topiramate is sold under the brand name Topamax. A combination product containing phentermine and topiramate extended-release called QSYMIA® is indicated for the management of obesity.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL205 |
5.0 nM [Ki] | ||
Target ID: CHEMBL3729 |
4.9 µM [Ki] | ||
Target ID: CHEMBL2326 |
0.9 nM [Ki] | ||
Target ID: CHEMBL3242 |
3.8 nM [Ki] | ||
Target ID: CHEMBL1962 Sources: http://www.drugbank.ca/drugs/DB00273 |
|||
Target ID: CHEMBL4789 |
63.0 nM [Ki] | ||
Target ID: CHEMBL3969 |
30.0 nM [Ki] | ||
Target ID: CHEMBL3912 |
47.0 nM [Ki] | ||
Target ID: CHEMBL1845 Sources: http://www.drugbank.ca/drugs/DB00273 |
|||
Target ID: CHEMBL2109241 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TOPAMAX Approved UseTOPAMAX is indicated for:
Monotherapy epilepsy: Initial monotherapy in patients > 2 years of age with partial onset or primary generalized tonic-clonic seizures
Adjunctive therapy epilepsy: Adjunctive therapy for adults and pediatric patients (2 to 16 years of age) with partial onset seizures or primary generalized tonic-clonic seizures, and in patients >2 years of age with
seizures associated with Lennox-Gastaut syndrome (LGS)
Migraine: Treatment for adults and adolescents 12 years of age and older for prophylaxis of migraine headache Launch Date1996 |
|||
| Preventing | TOPAMAX Approved UseTOPAMAX is indicated for:
Monotherapy epilepsy: Initial monotherapy in patients > 2 years of age with partial onset or primary generalized tonic-clonic seizures
Adjunctive therapy epilepsy: Adjunctive therapy for adults and pediatric patients (2 to 16 years of age) with partial onset seizures or primary generalized tonic-clonic seizures, and in patients >2 years of age with
seizures associated with Lennox-Gastaut syndrome (LGS)
Migraine: Treatment for adults and adolescents 12 years of age and older for prophylaxis of migraine headache Launch Date1996 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.63 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.46 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.98 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
3.68 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
18.38 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
28.73 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
59.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
57.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
311.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
350.3 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
20 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8930774 |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOPIRAMATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
59% |
unknown, unknown |
TOPIRAMATE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Topiramate selectively attenuates nicotine-induced increases in monoamine release. | 2001-12-01 |
|
| Intrinsic optical signals and electrographic seizures in the rat limbic system. | 2001-12 |
|
| Pharmacological characterization of the 6 Hz psychomotor seizure model of partial epilepsy. | 2001-12 |
|
| Clinical experience with topiramate dosing and serum levels in children 12 years or under with epilepsy. | 2001-11 |
|
| Bilateral angle-closure glaucoma and ciliary body swelling from topiramate. | 2001-11 |
|
| National survey on West syndrome in Korea. | 2001-11 |
|
| Review of treatment options for refractory epilepsy: new medications and vagal nerve stimulation. | 2001-11 |
|
| [Social and economic aspects of administration of new antiepileptic drugs]. | 2001-10-16 |
|
| Topiramate improves deficit symptoms in a patient with schizophrenia when added to a stable regimen of antipsychotic medication. | 2001-10-05 |
|
| Clinical and electroencephalographic effects of topiramate in patients with epilepsy and healthy volunteers. | 2001-10-05 |
|
| Hypohidrosis related to the administration of topiramate to children. | 2001-10 |
|
| Topiramate-induced metabolic acidosis: report of two cases. | 2001-10 |
|
| Plasma concentration of topiramate correlates with cerebrospinal fluid concentration. | 2001-10 |
|
| Quetiapine-related tardive dyskinesia. | 2001-10 |
|
| Topiramate-induced depression. | 2001-10 |
|
| Topiramate as a neuroprotectant in a rat model of global ischemia-induced neurodegeneration. | 2001-09-28 |
|
| Simple and rapid liquid chromatographic-turbo ion spray mass spectrometric determination of topiramate in human plasma. | 2001-09-15 |
|
| Antiepileptic drugs for the acute and maintenance treatment of bipolar disorder. | 2001-09-13 |
|
| Drug-resistant cluster headache responding to gabapentin: a pilot study. | 2001-09 |
|
| [Topiramate: an experience in children with partial epilepsy]. | 2001-09 |
|
| Re: Weight change with antipsychotic use. | 2001-09 |
|
| Postmarketing experience with topiramate and cognition. | 2001-09 |
|
| Topiramate for headaches. | 2001-09 |
|
| Weight loss with topiramate. | 2001-09 |
|
| Topiramate blocks perinatal hypoxia-induced seizures in rat pups. | 2001-09 |
|
| Topiramate as a mood stabilizer. | 2001-09 |
|
| Topiramate on ictal seizure semiology: a quantitative, randomized, low and medium dose-controlled study. | 2001-09 |
|
| Auditory hallucinations associated with topiramate. | 2001-08 |
|
| Confusion and dysphoria with low-dose topiramate in a patient with bipolar disorder. | 2001-08 |
|
| Newer antiepileptic drugs: advantages and disadvantages. | 2001-08 |
|
| Uveal effusion and secondary angle-closure glaucoma associated with topiramate use. | 2001-08 |
|
| First break of mania associated with topiramate treatment. | 2001-08 |
|
| Topiramate in venlafaxine-induced visual hallucinations in an obese patient with a posterior cerebral artery infarction. | 2001-08 |
|
| Panic attacks associated with the use of topiramate. | 2001-08 |
|
| Effect of tiagabine and topiramate on porphyrin metabolism in an in vivo model of porphyria. | 2001-07 |
|
| The role of new antiepileptic drugs. | 2001-07 |
|
| Incoercible topiramate-related vomiting in a patient with epilepsy and mental retardation. | 2001-06 |
|
| Topiramate for self-mutilation in a patient with borderline personality disorder. | 2001-06 |
|
| Topiramate abuse in a bipolar patient with an eating disorder. | 2001-06 |
|
| Antimanic efficacy of topiramate in 11 patients in an open trial with an on-off-on design. | 2001-06 |
|
| Developments in mood stabilisers. | 2001 |
|
| Cutaneous drug reaction case reports: from the world literature. | 2001 |
|
| Comparative efficacy and tolerability of drug treatments for bipolar disorder. | 2001 |
|
| Concerns with antiepileptic drug initiation: safety, tolerability, and efficacy. | 2001 |
|
| Adverse effects of antiepileptic drugs on bone structure: epidemiology, mechanisms and therapeutic implications. | 2001 |
|
| The management of refractory idiopathic epilepsies. | 2001 |
|
| Management strategies for refractory localization-related seizures. | 2001 |
|
| Topiramate in posttraumatic stress disorder: preliminary clinical observations. | 2001 |
|
| The new generation of GABA enhancers. Potential in the treatment of epilepsy. | 2001 |
|
| Cognitive side effects of anticonvulsants. | 2001 |
Sample Use Guides
Recommended dose: 400 mg orally per day in 2 divided doses of 200 mg each
The dose should be achieved by titration:
Week 1: 25 mg orally in the morning and 25 mg orally in the evening
Week 2: 50 mg orally in the morning and 50 mg orally in the evening
Week 3: 75 mg orally in the morning and 75 mg orally in the evening
Week 4: 100 mg orally in the morning and 100 mg orally in the evening
Week 5: 150 mg orally in the morning and 150 mg orally in the evening
Week 6: 200 mg orally in the morning and 200 mg orally in the evening
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 10:17:10 GMT 2025
by
admin
on
Wed Apr 02 10:17:10 GMT 2025
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| Record UNII |
N808MSN0PT
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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23663532
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DBSALT002318
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N808MSN0PT
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SOLVATE->ANHYDROUS |
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