Identification

Name
Topiramate
Accession Number
DB00273  (APRD00237)
Type
Small Molecule
Groups
Approved
Description

Topiramate (brand name Topamax) is an anticonvulsant drug produced by Ortho-McNeil Neurologics, a division of Johnson & Johnson. It is used to treat epilepsy in both children and adults. In children it is also indicated for treatment of Lennox-Gastaut syndrome (a disorder that causes seizures and developmental delays). It is also Food and Drug Administration (FDA) approved for, and now most frequently prescribed for, the prevention of migraines. [Wikipedia]. A combination product containing phentermine and topiramate extended-release called QSYMIA® is indicated for the management of obesity. On August 2013, an extended released formulation, marketed as Trokendi XR has been approved for the management of partial onset, tonic-clonic, and Lennox-Gastaut Syndrome seizures.

Structure
Thumb
Synonyms
  • 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate
  • 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate
  • McN-4853
  • RWJ-17021
  • Tipiramate
  • Tipiramato
  • Topiramate
  • Topiramato
  • Topiramatum
  • TPM
External IDs
RWJ-17021-000 / USL-255 / USL255
Product Ingredients
IngredientUNIICASInChI Key
Topiramate calciumP956SY6RA61246279-00-4VNRLRDKZOMPUAG-RZTSBURASA-N
Topiramate potassiumSMU8E1YBZ3488127-51-1VEKVPJSPZRTTGR-WGAVTJJLSA-N
Topiramate sodiumN808MSN0PT488127-49-7ZUWVVMMRNQEJMW-WGAVTJJLSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act TopiramateTablet25 mgOralActavis Pharma Company2007-07-12Not applicableCanada
Act TopiramateTablet200 mgOralActavis Pharma Company2007-07-12Not applicableCanada
Act TopiramateTablet100 mgOralActavis Pharma Company2007-07-12Not applicableCanada
Gln-topiramateTablet100 mgOralGlenmark Pharmaceuticals, IncNot applicableNot applicableCanada
Gln-topiramateTablet25 mgOralGlenmark Pharmaceuticals, IncNot applicableNot applicableCanada
Gln-topiramateTablet200 mgOralGlenmark Pharmaceuticals, IncNot applicableNot applicableCanada
Q-topiramateTablet100 mgOralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada
Q-topiramateTablet25 mgOralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada
Q-topiramateTablet200 mgOralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Qudexy XRCapsule, extended release150 mg/1OralUpsher-Smith Laboratories, Inc.2014-04-11Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abbott-topiramateTablet200 mgOralBgp Pharma Ulc2014-03-172015-12-31Canada
Abbott-topiramateTablet100 mgOralBgp Pharma Ulc2014-03-122015-12-31Canada
Abbott-topiramateTablet25 mgOralBgp Pharma Ulc2014-03-122015-12-31Canada
Accel-topiramateTablet100 mgOralAccel Pharma Inc2015-03-262017-01-27Canada
Accel-topiramateTablet25 mgOralAccel Pharma Inc2015-03-262017-01-27Canada
Accel-topiramateTablet200 mgOralAccel Pharma Inc2015-03-262017-01-27Canada
Apo-topiramateTablet200 mgOralApotex Corporation2006-04-21Not applicableCanada
Apo-topiramateTablet25 mgOralApotex Corporation2006-04-21Not applicableCanada
Apo-topiramateTablet100 mgOralApotex Corporation2006-04-21Not applicableCanada
Apo-topiramateTablet50 mgOralApotex CorporationNot applicableNot applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
QsymiaTopiramate (69 mg/1) + Phentermine Hydrochloride (11.25 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
QsymiaTopiramate (23 mg/1) + Phentermine Hydrochloride (3.75 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
QsymiaTopiramate (92 mg/1) + Phentermine Hydrochloride (15 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
QsymiaTopiramate (46 mg/1) + Phentermine Hydrochloride (7.5 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
International/Other Brands
Topamax
Categories
UNII
0H73WJJ391
CAS number
97240-79-4
Weight
Average: 339.362
Monoisotopic: 339.098787343
Chemical Formula
C12H21NO8S
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[7.3.0.0²,⁶]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

Pharmacology

Indication

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. Qsymia® is indicated for the treatment and management of obesity.

Associated Conditions
Pharmacodynamics

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.

Mechanism of action

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 GABAA receptor (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.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
agonist
Human
ASodium channel protein type 1 subunit alpha
inhibitor
Human
AGlutamate receptor ionotropic, kainate 1
antagonist
Human
ACarbonic anhydrase 2
inhibitor
Human
ACarbonic anhydrase 4
inhibitor
Human
AGABA-A receptor (anion channel)
positive allosteric modulator
Human
UCarbonic anhydrase 1
inhibitor
Human
UCarbonic anhydrase 3
inhibitor
Human
Absorption

Rapid with pleak plasma concentrations occurring after 2 hours and a bioavailability of 80%. The pharmacokinetic profile of the extended release formulation is non linear at 25 mg due to binding of topiramate to carbonic anhydrase in red blood cells. The peak plasma concentration was 24 hours after a single 200 mg oral dose of the extended release formulation. It is also bioequivalent to immediate-release tablet that has been administered twice-daily. Fluctuation of topiramate plasma concentrations at steady-state for Trokendi XR™ administered once-daily was approximately 26% and 42% in healthy subjects and in epileptic patients, respectively, compared to approximately 40% and 51%, respectively, for immediate-release topiramate. When topiramate is given to elderly and young adults, the maximum plasma concentration was achieved in 1 to 2 hours.

Volume of distribution
Not Available
Protein binding

15-41% (over the blood concentration range of 0.5 - 250 mg/mL). The fraction bound decreased as blood concentration increased. Carbamazepine and phenytoin do not alter the binding of immediate-release topiramate. Sodium valproate, at 500 mcg/mL (a concentration 5 to 10 times higher than considered therapeutic for valproate) decreased the protein binding of immediate-release topiramate from 23% to 13%. Immediate-release topiramate does not influence the binding of sodium valproate.

Metabolism

Not extensively metabolized, 70% of the dose is eliminated unchanged in the urine. The other 30% is metabolized hepatically to six metabolites (formed by hydroxylation, hydrolysis, and glucuronidation), none of which constitute more than 5% of an administered dose. There is evidence of renal tubular reabsorption of topiramate.

Route of elimination

Topiramate is not extensively metabolized and is primarily eliminated unchanged in the urine (approximately 70% of an administered dose).

Half life

19 to 23 hours. The mean elimination half-life was 31 hours following repeat administration of the extended-release formulation.

Clearance
  • Plasma clearance (CL/F) =20-30 mL/min [in humans following oral administration] Clearance in adults was not affected by gender or race. Pediatric patients on adjunctive treatment exhibited a higher oral clearance compared to those on monotherapy. This may be because of concomitant administration with enzyme-inducing antiepileptic drugs.
Toxicity

Symptoms of overdose include abdominal pain, agitation, blurred vision, convulsions, depression, dizziness, double vision, drowsiness, impaired coordination, impaired mental activity, low blood pressure, reduced consciousness, severe diarrhea, sluggishness, and speech problems.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Topiramate.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Topiramate.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Topiramate is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineTopiramate may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Topiramate is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Topiramate.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Topiramate is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Topiramate.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Topiramate is combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Topiramate.
Food Interactions
  • Following a single dose of the extended-release formulation with a high fat meal, Cmax of topiramate increased by 37% and shortened the Tmax to approximately 8 hours. AUC was not effected. According to the FDA label, Trokendi XR can be taken without regard to food.

References

Synthesis Reference

Orn Almarsson, "Topiramate salts and compositions comprising and methods of making and using the same." U.S. Patent US20040053853, issued March 18, 2004.

US20040053853
General References
  1. Blum D, Meador K, Biton V, Fakhoury T, Shneker B, Chung S, Mills K, Hammer A, Isojarvi J: Cognitive effects of lamotrigine compared with topiramate in patients with epilepsy. Neurology. 2006 Aug 8;67(3):400-6. [PubMed:16894098]
External Links
Human Metabolome Database
HMDB0005034
KEGG Drug
D00537
KEGG Compound
C07502
PubChem Compound
5284627
PubChem Substance
46508334
ChemSpider
4447672
BindingDB
10887
ChEBI
63631
ChEMBL
CHEMBL220492
Therapeutic Targets Database
DAP000137
PharmGKB
PA451728
HET
TOR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Topiramate
ATC Codes
N03AX11 — Topiramate
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
PDB Entries
3hku / 3lxe / 5jna
FDA label
Download (236 KB)
MSDS
Download (57.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentSleep-Related Eating Disorder1
0TerminatedPreventionEpilepsies / Traumatic Brain Injury (TBI)1
1Active Not RecruitingPreventionCyanotic Congenital Heart Disease1
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableSeizures1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedScreeningHealthy Volunteers2
1CompletedTreatmentAlcohol Dependence1
1CompletedTreatmentAlteration of Cognitive Function1
1CompletedTreatmentBMI >30 kg/m21
1CompletedTreatmentBinge Eating Disorder (BED) / Bulimia Nervosa (BN)1
1CompletedTreatmentBipolar Disorder (BD)2
1CompletedTreatmentEpilepsies2
1CompletedTreatmentEpilepsies / Migraines1
1CompletedTreatmentHepatic Impairment1
1CompletedTreatmentHuman Volunteers / Migraines1
1Not Yet RecruitingPreventionMigraines1
1Not Yet RecruitingTreatmentContraception / Migraine;Menstrual / Migraines1
1RecruitingBasic ScienceCocaine Use Disorders1
1, 2CompletedTreatmentSleep Apnea Syndrome1
1, 2RecruitingTreatmentAlcohol Drinking1
1, 2RecruitingTreatmentHypoxic Ischemic Encephalopathy (HIE)1
2Active Not RecruitingTreatmentBariatric Surgery Procedures / BMI >30 kg/m2 / Metabolic Surgery / Obese experiencing rapid weight loss1
2Active Not RecruitingTreatmentBMI >30 kg/m2 / Obese experiencing rapid weight loss / Obesity, Morbid1
2CompletedNot AvailableTobacco Use Disorders1
2CompletedBasic ScienceAlcohol Dependence1
2CompletedBasic ScienceCocaine-Related Disorders1
2CompletedEducational/Counseling/TrainingBasilar Migraine1
2CompletedTreatmentAlcohol Dependence1
2CompletedTreatmentAlcohol Dependence / Binge Eating1
2CompletedTreatmentAlcohol Dependence / Dependence, Cocaine1
2CompletedTreatmentAlcohol Dependence / Nicotine Dependence1
2CompletedTreatmentBMI >30 kg/m22
2CompletedTreatmentBMI >30 kg/m2 / Diabetes Mellitus, Adult-Onset / Type 2 Diabetes Mellitus2
2CompletedTreatmentBinge Eating Disorder (BED)1
2CompletedTreatmentCannabis Abuse / Cannabis Dependence1
2CompletedTreatmentCompulsive Shopping1
2CompletedTreatmentDependence, Cocaine2
2CompletedTreatmentDiabetes Mellitus (DM)1
2CompletedTreatmentDiabetic Neuropathies / Polyneuropathies / Type 2 Diabetes Mellitus1
2CompletedTreatmentEpilepsies / Epilepsy, Localization Related / Seizures5
2CompletedTreatmentEpilepsy, Absence1
2CompletedTreatmentHeadaches1
2CompletedTreatmentMethamphetamine1
2CompletedTreatmentMigraines2
2CompletedTreatmentSciatica1
2Not Yet RecruitingTreatmentPost Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentAlcohol Dependence1
2RecruitingTreatmentCryptogenic Sensory Peripheral Neuropathy / Cryptogenic Sensory Peripheral Neuropathy in Metabolic Syndrome1
2SuspendedTreatmentBMI >30 kg/m2 / Metabolic Syndromes1
2TerminatedTreatmentAlcohol Abuse / Alcohol Dependence1
2TerminatedTreatmentAlcohol Dependence / Heavy Drinking / Human Immunodeficiency Virus (HIV)1
2TerminatedTreatmentAlcohol Drinking1
2TerminatedTreatmentDrug Induced Dyskinesia / Idiopathic Parkinson's Disease1
2TerminatedTreatmentHeadaches / Migraines1
2TerminatedTreatmentParkinson's Disease (PD)1
2Unknown StatusTreatmentAlcohol Dependence1
2Unknown StatusTreatmentDisseminated Sclerosis1
2WithdrawnTreatmentGambling1
2, 3CompletedNot AvailableBasilar Migraine1
2, 3CompletedTreatmentAlcohol Dependence2
2, 3CompletedTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m21
2, 3CompletedTreatmentDependence, Cocaine1
2, 3CompletedTreatmentPosttraumatic Stress Disorders1
2, 3RecruitingTreatmentPTSD and Alcohol Use Disorder1
2, 3Unknown StatusTreatmentAlcohol Dependence / Nicotine Dependence1
3CompletedPreventionChronic Migraine1
3CompletedPreventionHeadaches / Migraines1
3CompletedPreventionMigraines4
3CompletedTreatmentAffective Disorders, Psychotic / Bipolar Disorder (BD) / Moods Disorders1
3CompletedTreatmentAffective Disorders, Psychotic / Bipolar Disorder (BD) / Moods Disorders / Psychiatric Disorder NOS1
3CompletedTreatmentBMI >30 kg/m24
3CompletedTreatmentBMI >30 kg/m2 / Diabetes Mellitus, Adult-Onset / Type 2 Diabetes Mellitus2
3CompletedTreatmentBMI >30 kg/m2 / High Blood Pressure (Hypertension)1
3CompletedTreatmentBinge Eating1
3CompletedTreatmentBipolar Disorder (BD)3
3CompletedTreatmentCessation, Smoking1
3CompletedTreatmentClassic Migraine / Headaches / Migraine Without Aura / Migraines3
3CompletedTreatmentEpilepsies3
3CompletedTreatmentEpilepsies / Epilepsy, Generalized / Epilepsy, Localization Related / Epilepsy, Tonic-Clonic / Seizures1
3CompletedTreatmentEpilepsies / Epilepsy, Generalized / Epilepsy, Localization Related / Seizures1
3CompletedTreatmentEpilepsies / Epilepsy, Localization Related / Seizures2
3CompletedTreatmentEpilepsies / Seizure Disorder, Partial / Seizures1
3CompletedTreatmentEpilepsies / Seizures5
3CompletedTreatmentGilles de la Tourette's Syndrome2
3CompletedTreatmentLennox-Gastaut Syndrome (LGS)1
3CompletedTreatmentMigraines2
3CompletedTreatmentMigraines / Vascular Headaches2
3CompletedTreatmentObese Children and Adolescents1
3CompletedTreatmentObsessive Compulsive Disorder (OCD)1
3CompletedTreatmentTobacco Dependence1
3CompletedTreatmentTremor, Essential1
3RecruitingHealth Services ResearchEpilepsies1
3RecruitingTreatmentAlcohol Dependence1
3RecruitingTreatmentBMI >30 kg/m21
3RecruitingTreatmentBMI >30 kg/m2 / Polycystic Ovaries Syndrome1
3SuspendedTreatmentMetabolic Syndromes / Type 2 Diabetes Mellitus1
3TerminatedPreventionHeadaches / Migraine Disorders / Migraines1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentBMI >30 kg/m2 / Diabetes Mellitus, Adult-Onset / Type 2 Diabetes Mellitus1
3TerminatedTreatmentBMI >30 kg/m2 / Hyperlipidemias / Hypertriglyceridemias1
3TerminatedTreatmentEpilepsies / Seizures1
3TerminatedTreatmentPrader-Willi Syndrome1
3Unknown StatusTreatmentAlcohol Dependence / Dependence, Cocaine1
3Unknown StatusTreatmentCocaine-Related Disorders1
3WithdrawnTreatmentAlcohol Dependence / Borderline Personality Disorder (BPD)1
3WithdrawnTreatmentAlcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
4Active Not RecruitingTreatmentBMI >30 kg/m21
4CompletedNot AvailableCognitive Deficits1
4CompletedNot AvailableConvulsions / Epilepsies / Osteopenia / Osteoporosis / Seizures1
4CompletedNot AvailableEpilepsies1
4CompletedNot AvailableMigraines1
4CompletedEducational/Counseling/TrainingRestless Legs Syndrome (RLS)1
4CompletedPreventionMigraine Disorders1
4CompletedPreventionMigraines1
4CompletedTreatmentAlcohol Abuse / Alcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentAlcohol Abuse / Bipolar Disorder (BD)1
4CompletedTreatmentAlcohol Dependence1
4CompletedTreatmentAlcohol Dependence / Bipolar Disorder (BD)1
4CompletedTreatmentAlcohol Drinking1
4CompletedTreatmentBMI >30 kg/m22
4CompletedTreatmentBipolar Disorder (BD) / Cannabis-Related Disorder1
4CompletedTreatmentBipolar Disorder (BD) / Weight gain therapy1
4CompletedTreatmentChronic Migraine2
4CompletedTreatmentClassic Migraine / Headaches / Migraine Without Aura / Migraines1
4CompletedTreatmentEpilepsies4
4CompletedTreatmentEpilepsies / Epilepsy, Generalized / Epilepsy, Localization Related / Grand mal Generalized tonic-clonic seizure / Seizures1
4CompletedTreatmentEpilepsy, Localization Related1
4CompletedTreatmentEpilepsy, Rolandic1
4CompletedTreatmentHazardous and Harmful Alcohol Use / Traumatic Brain Injury (TBI)1
4CompletedTreatmentMigraine Disorders1
4CompletedTreatmentObesity, Childhood / Pediatric Obesity1
4CompletedTreatmentPost Traumatic Stress Disorder (PTSD)2
4CompletedTreatmentPosttraumatic Stress Disorders1
4Not Yet RecruitingTreatmentEpilepsy, Localization Related1
4Not Yet RecruitingTreatmentMigraines1
4RecruitingNot AvailableEpilepsies1
4RecruitingTreatmentAlcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
4RecruitingTreatmentAlcohol Use Disorder (AUD)1
4RecruitingTreatmentEpilepsies1
4RecruitingTreatmentObsessive Compulsive Disorder (OCD)1
4RecruitingTreatmentSocial Phobia1
4TerminatedPreventionVomiting1
4TerminatedTreatmentCluster Headache1
4TerminatedTreatmentHeadaches1
4Unknown StatusNot AvailableEpilepsies1
4Unknown StatusPreventionAnalgesic Rebound Headache1
4Unknown StatusTreatmentAlcohol Dependence1
4Unknown StatusTreatmentGlaucoma, Angle-Closure1
4Unknown StatusTreatmentObsessive Compulsive Disorder (OCD)1
4Unknown StatusTreatmentPathological Gambling1
4WithdrawnTreatmentBulimia Nervosa (BN)1
Not AvailableCompletedNot AvailableAcute Gouty Arthritis / Arthritis / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableCompletedNot AvailableEpilepsies / Seizures1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableMigraine Disorders1
Not AvailableCompletedNot AvailableSeizures, Epileptic1
Not AvailableCompletedTreatmentBMI >30 kg/m21
Not AvailableCompletedTreatmentBulimia Nervosa (BN) / Eating Disorders1
Not AvailableCompletedTreatmentMigraines2
Not AvailableCompletedTreatmentPatients With Chronic Migraine1
Not AvailableCompletedTreatmentPrader-Willi Syndrome / Self-Injurious Behavior1
Not AvailableCompletedTreatmentRett's Syndrome1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / Gynaecological infection / Headaches / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperlipidemias / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain NOS / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailableEpilepsies1
Not AvailableRecruitingTreatmentMigraine Disorders / Vestibular Migraine1
Not AvailableRecruitingTreatmentSchizophrenia, Schizoaffective Disorder1
Not AvailableSuspendedTreatmentCocaine-Related Disorders / Opioid-Related Disorders1
Not AvailableTerminatedTreatmentAlcohol Abuse / Alcohol Dependence / Alcohol Use Disorder (AUD) / Post Traumatic Stress Disorder (PTSD) / Posttraumatic Stress Disorders1
Not AvailableTerminatedTreatmentParkinson's Disease (PD)1
Not AvailableUnknown StatusNot AvailableHeadaches Chronic / Migraines1
Not AvailableUnknown StatusHealth Services ResearchMigraines1
Not AvailableWithdrawnTreatmentDizziness / Headaches / Migraines1
Not AvailableWithdrawnTreatmentMigraines1

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
FormRouteStrength
TabletOral50 mg
Capsule, extended releaseOral
Capsule, extended releaseOral150 mg/1
Capsule, extended releaseOral200 mg/1
TabletOral200 1/1
TabletOral25 meq/1
CapsuleOral15 mg
CapsuleOral25 mg
Capsule, coated pelletsOral15 mg/1
Capsule, coated pelletsOral25 mg/1
TabletOral100 mg
TabletOral200 mg
TabletOral25 mg
Tablet, coatedOral100 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral25 mg/1
Tablet, coatedOral50 mg/1
CapsuleOral15 mg/1
CapsuleOral25 mg/1
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral25 mg/1
Capsule, extended releaseOral50 mg/1
TabletOral100 mg/1
TabletOral200 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
Prices
Unit descriptionCostUnit
Topiramate 200 mg tablet8.32USD tablet
Topamax 200 mg tablet7.68USD tablet
Topiramate 100 mg tablet7.11USD tablet
Topamax 100 mg tablet6.31USD tablet
Topamax 50 mg tablet5.96USD tablet
Topiramate 50 mg tablet5.21USD tablet
Topiramate 25 mg Sprinkle Capsule3.04USD capsule
Topiramate 25 mg tablet2.61USD tablet
Topiramate 99.7% powder2.59USD g
Topiramate 15 mg Sprinkle Capsule2.52USD capsule
Topamax 25 mg tablet2.46USD tablet
Co Topiramate 200 mg Tablet2.08USD tablet
Mylan-Topiramate 200 mg Tablet2.08USD tablet
Novo-Topiramate 200 mg Tablet2.08USD tablet
Phl-Topiramate 200 mg Tablet2.08USD tablet
Pms-Topiramate 200 mg Tablet2.08USD tablet
Ratio-Topiramate 200 mg Tablet2.08USD tablet
Sandoz Topiramate 200 mg Tablet2.08USD tablet
Topamax Sprinkle 25 mg Capsule1.35USD capsule
Sandoz Topiramate 100 mg Tablet1.31USD tablet
Co Topiramate 100 mg Tablet1.31USD tablet
Mylan-Topiramate 100 mg Tablet1.31USD tablet
Novo-Topiramate 100 mg Tablet1.31USD tablet
Phl-Topiramate 100 mg Tablet1.31USD tablet
Pms-Topiramate 100 mg Tablet1.31USD tablet
Ratio-Topiramate 100 mg Tablet1.31USD tablet
Topamax Sprinkle 15 mg Capsule1.29USD capsule
Pms-Topiramate 50 mg Tablet1.05USD tablet
Co Topiramate 25 mg Tablet0.69USD tablet
Mylan-Topiramate 25 mg Tablet0.69USD tablet
Novo-Topiramate 25 mg Tablet0.69USD tablet
Phl-Topiramate 25 mg Tablet0.69USD tablet
Pms-Topiramate 25 mg Tablet0.69USD tablet
Ratio-Topiramate 25 mg Tablet0.69USD tablet
Sandoz Topiramate 25 mg Tablet0.69USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2322644No2005-07-262019-03-01Canada
US5998380Yes1996-04-132016-04-13Us
US6503884Yes1996-04-132016-04-13Us
US7018983Yes1996-04-132016-04-13Us
US7498311Yes1996-04-132016-04-13Us
US7125560Yes1999-09-012019-09-01Us
US6071537No1997-06-232017-06-23Us
US8895057No2008-06-092028-06-09Us
US7056890No2000-06-142020-06-14Us
US7553818No2000-06-142020-06-14Us
US7659256No2000-06-142020-06-14Us
US7674776No2000-06-142020-06-14Us
US8580299No2009-06-142029-06-14Us
US9011906No2008-06-092028-06-09Us
US9011905No2008-06-092028-06-09Us
US8895058No2008-06-092028-06-09Us
US8580298No2009-05-152029-05-15Us
US9101545No2013-03-192033-03-19Us
US8652527No2013-03-192033-03-19Us
US8889190No2013-03-192033-03-19Us
US8889191No2007-11-162027-11-16Us
US8298580No2007-11-162027-11-16Us
US8663683No2007-11-162027-11-16Us
US8877248No2007-11-162027-11-16Us
US8298576No2008-04-042028-04-04Us
US8992989No2007-11-162027-11-16Us
US9555005No2013-03-192033-03-19Us
US9549940No2007-11-162027-11-16Us
US9555004No2007-11-162027-11-16Us
US9622983No2007-11-162027-11-16Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility9.8 mg/mLNot Available
logP-0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.8 mg/mLALOGPS
logP1.29ALOGPS
logP0.13ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.09ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area115.54 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.3 m3·mol-1ChemAxon
Polarizability32.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9955
Blood Brain Barrier+0.9382
Caco-2 permeable-0.6055
P-glycoprotein substrateNon-substrate0.7905
P-glycoprotein inhibitor INon-inhibitor0.5311
P-glycoprotein inhibitor IINon-inhibitor0.9479
Renal organic cation transporterNon-inhibitor0.9131
CYP450 2C9 substrateNon-substrate0.9479
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.542
CYP450 1A2 substrateNon-inhibitor0.6623
CYP450 2C9 inhibitorNon-inhibitor0.7259
CYP450 2D6 inhibitorNon-inhibitor0.8674
CYP450 2C19 inhibitorNon-inhibitor0.6539
CYP450 3A4 inhibitorNon-inhibitor0.8469
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7952
Ames testAMES toxic0.518
CarcinogenicityNon-carcinogens0.5578
BiodegradationNot ready biodegradable0.9803
Rat acute toxicity2.5682 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8882
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-01q9-2960000000-a11a150bcada5055d2e9
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014i-0090000000-c1fa3d6ff15890fc1418
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0059000000-a6337903cab01edce60e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0239000000-994a7b97e101c455a792
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38

Taxonomy

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
Dioxolopyran / Ketal / Oxane / Monosaccharide / Organic sulfuric acid or derivatives / Meta-dioxolane / Oxacycle / Acetal / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cyclic ketal, sulfamate ester, ketohexose derivative (CHEBI:63631)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Nowakowska E, Kus K, Czubak A, Jedrzejewska J: Memory improving and antidepressant effects of topiramate in rats. Arzneimittelforschung. 2009;59(10):487-92. doi: 10.1055/s-0031-1296431. [PubMed:19998575]
  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. [PubMed:19417176]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific 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...
Gene Name
SCN1A
Uniprot ID
P35498
Uniprot Name
Sodium channel protein type 1 subunit alpha
Molecular Weight
228969.49 Da
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. [PubMed:11948006]
  2. Ceulemans B, Cras P: "Severe myoclonic epilepsy in infancy". Relevance for the clinician of severe epilepsy starting in infancy. Acta Neurol Belg. 2004 Sep;104(3):95-9. [PubMed:15508261]
  3. 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. [PubMed:15526956]
  4. Korff C, Laux L, Kelley K, Goldstein J, Koh S, Nordli D Jr: Dravet syndrome (severe myoclonic epilepsy in infancy): a retrospective study of 16 patients. J Child Neurol. 2007 Feb;22(2):185-94. [PubMed:17621480]
  5. 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. [PubMed:12861512]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated cation channel activity
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name
GRIK1
Uniprot ID
P39086
Uniprot Name
Glutamate receptor ionotropic, kainate 1
Molecular Weight
103979.665 Da
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. [PubMed:12724156]
  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. [PubMed:12904467]
  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. [PubMed:15111016]
  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. [PubMed:19417176]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Details
4. Carbonic anhydrase 2
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
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. [PubMed:15771438]
  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. [PubMed:17521680]
  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. [PubMed:17251017]
  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. [PubMed:12617904]
  5. Winum JY, Scozzafava A, Montero JL, Supuran CT: Sulfamates and their therapeutic potential. Med Res Rev. 2005 Mar;25(2):186-228. [PubMed:15478125]
Details
5. Carbonic anhydrase 4
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina an...
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. [PubMed:14684331]
  2. Dodgson SJ, Shank RP, Maryanoff BE: Topiramate as an inhibitor of carbonic anhydrase isoenzymes. Epilepsia. 2000;41 Suppl 1:S35-9. [PubMed:10768298]
  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. [PubMed:11784136]
  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. [PubMed:14971907]
Details
7. Carbonic anhydrase 1
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
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. [PubMed:17826101]
Details
8. Carbonic anhydrase 3
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
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. [PubMed:17826101]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Nallani SC, Glauser TA, Hariparsad N, Setchell K, Buckley DJ, Buckley AR, Desai PB: Dose-dependent induction of cytochrome P450 (CYP) 3A4 and activation of pregnane X receptor by topiramate. Epilepsia. 2003 Dec;44(12):1521-8. [PubMed:14636322]
  3. Benedetti MS: Enzyme induction and inhibition by new antiepileptic drugs: a review of human studies. Fundam Clin Pharmacol. 2000 Jul-Aug;14(4):301-19. [PubMed:11030437]

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 12:40