Category:pharmaceuticals / chemical synthisis
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Assay: | 95.00 to 100.00
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Food Chemicals Codex Listed: | No |
Boiling Point: | 438.70 °C. @ 760.00 mm Hg (est)
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Flash Point: | 426.00 °F. TCC ( 219.10 °C. ) (est)
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logP (o/w): | 2.970 (est) |
Soluble in: |
| water, 1.364e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
Preferred SDS: View |
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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Hazard statement(s) |
None found. |
Precautionary statement(s) |
None found. |
Oral/Parenteral Toxicity: |
intraperitoneal-rat LD50 > 1500 mg/kg Drugs of the Future. Vol. 14, Pg. 342, 1989.
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Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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Safety in Use Information:
Category: | pharmaceuticals / chemical synthisis |
Recommendation for topiramate usage levels up to: | | not for fragrance use.
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Recommendation for topiramate flavor usage levels up to: |
| not for flavor use.
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Safety References:
EPI System: View |
ClinicalTrials.gov:search |
Daily Med:search |
AIDS Citations:Search |
Cancer Citations:Search |
Toxicology Citations:Search |
EPA ACToR:Toxicology Data |
EPA Substance Registry Services (SRS):Registry |
Laboratory Chemical Safety Summary :56840897 |
National Institute of Allergy and Infectious Diseases:Data |
WGK Germany:3 |
[(3aS,5aR,8aR)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate |
Chemidplus:0097240794 |
RTECS:LS7083000 for cas# 97240-79-4 |
References:
| [(3aS,5aR,8aR)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate |
NIST Chemistry WebBook: | Search Inchi |
Pubchem (cid): | 56840897 |
Pubchem (sid): | 135016312 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| epitomax | 2,3:4,5-bis-O-(1- | methylethylidene)-b-D-fructopyranose sulfamate | [(3aS,5aR,8aR)-2,2,7,7- | tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate | | topamax | | | topiramatum | | topomax |
Articles:
PubMed:Pharmacogenetics of alcohol use disorders and comorbid psychiatric disorders. |
PubMed:Antimuscarinic-induced convulsions in fasted animals after food intake: evaluation of the effects of levetiracetam, topiramate and different doses of atropine. |
PubMed:High-Dose Loperamide Abuse Inducing Life-Threatening Cardiac Arrhythmias; Topiramate-Induced Diarrhea in a Breastfed Infant; Danazol-Induced Stevens-Johnson Syndrome; Asenapine-Induced Myasthenic Syndrome; Black Hairy Tongue Due to Linezolid; Adalimumab-Induced Priapism. |
PubMed:Modified-Release Formulations of Second-Generation Antiepileptic Drugs: Pharmacokinetic and Clinical Aspects. |
PubMed:Obesity medications: what does the future look like? |
PubMed:[The pharmacotherapy of obesity]. |
PubMed:Phentermine-topiramate: First combination drug for obesity. |
PubMed:Migraine headache in children. |
PubMed:Paradoxical topiramate-induced hyperphagia successfully treated with phentermine in a woman with migraine. |
PubMed:Safety and tolerability of medications approved for chronic weight management. |
PubMed:Past and present of antiobesity agents: focus on monoamine modulators. |
PubMed:The development or exacerbation of eating disorder symptoms after topiramate initiation. |
PubMed:Optimal management of night eating syndrome: challenges and solutions. |
PubMed:New molecular targets in the pathophysiology of obesity and available treatment options under investigation. |
PubMed:ANTI-OBESITY PHARMACOTHERAPY AND THE POTENTIAL FOR PREVENTING PROGRESSION FROM PREDIABETES TO TYPE 2 DIABETES. |
PubMed:Drug treatment of obesity: current status and future prospects. |
PubMed:Pharmacotherapy for obesity. |
PubMed:Antiobesity pharmacotherapy for patients with type 2 diabetes: focus on long-term management. |
PubMed:Report of the WPA section of pharmacopsychiatry on the relationship of antiepileptic drugs with suicidality in epilepsy. |
PubMed:Is antiepileptic-induced suicidality a data-based class effect or an exaggeration? A comment on the literature. |
PubMed:Pharmacological management of obesity in pediatric patients. |
PubMed:Royal Australian and New Zealand College of Psychiatrists clinical practice guidelines for the treatment of eating disorders. |
PubMed:Migraine headache prophylaxis in adolescents. |
PubMed:Modern obesity pharmacotherapy: weighing cardiovascular risk and benefit. |
PubMed:USL255 extended-release topiramate for the treatment of epilepsy. |
PubMed:FDA approves Topamax for migraine prevention in adolescents. |
PubMed:New drug therapies for the treatment of overweight and obese patients. |
PubMed:Topiramate's reduction of body mass index in heavy drinkers: lack of moderation by a GRIK1 polymorphism. |
PubMed:Topiramate: antipsychotic-induced weight gain. |
PubMed:Treatment of Gambling Disorders. |
PubMed:New pharmacological treatments for the management of obesity. |
PubMed:Connective tissue disease following hepatitis B vaccination; topiramate-associated fatal heat stroke; ramelteon-induced autoimmune hepatitis; acute oxaliplatin-induced thrombotic thrombocytopenic purpura. |
PubMed:2013 new drug update: what do new approvals hold for the elderly? |
PubMed:Larval zebrafish model for FDA-approved drug repositioning for tobacco dependence treatment. |
PubMed:PTSD and comorbid AUD: a review of pharmacological and alternative treatment options. |
PubMed:Cardiovascular effects of phentermine and topiramate: a new drug combination for the treatment of obesity. |
PubMed:Pharmacotherapy of alcohol use disorders: seventy-five years of progress. |
PubMed:Management of obesity and cardiometabolic risk - role of phentermine/extended release topiramate. |
PubMed:The new weight-loss drugs, lorcaserin and phentermine-topiramate: slim pickings? |
PubMed:A review of the metabolic effects of controlled-release Phentermine/Topiramate. |
PubMed:Weight loss strategies for treatment of obesity. |
PubMed:New antiobesity agents: lorcaserin (Belviq) and phentermine/topiramate ER (Qsymia). |
PubMed:Obesity consults--comprehensive obesity management in 2013: understanding the shifting paradigm. |
PubMed:The efficacy of a low dose combination of topiramate and naltrexone on ethanol reinforcement and consumption in rat models. |
PubMed:Can medical therapy mimic the clinical efficacy or physiological effects of bariatric surgery? |
PubMed:Update on pharmacology of obesity: benefits and risks. |
PubMed:New tools for weight-loss therapy enable a more robust medical model for obesity treatment: rationale for a complications-centric approach. |
PubMed:New medications for obesity management: changing the landscape of obesity treatment. |
PubMed:Drug treatment of obesity in the cardiovascular patient. |
PubMed:Update on treatment of essential tremor. |
PubMed:Determination of topiramate in human plasma using liquid chromatography tandem mass spectrometry. |
PubMed:Evaluation of lorcaserin for the treatment of obesity. |
PubMed:New obesity agents: lorcaserin and phentermine/topiramate. |
PubMed:Behavioral characteristics and pharmacological manipulations of a nicotine-entrainable circadian oscillator. |
PubMed:Pharmacologic treatment options for obesity: what is old is new again. |
PubMed:Fully validated method for rapid and simultaneous measurement of six antiepileptic drugs in serum and plasma using ultra-performance liquid chromatography-electrospray ionization tandem mass spectrometry. |
PubMed:Lorcaserin: a novel serotonin 2C agonist for the treatment of obesity. |
PubMed:Effective dose of topiramate in pediatric migraine prophylaxis. |
PubMed:Pharmacotherapy of obesity: clinical treatments and considerations. |
PubMed:Development and validation of dried blood spots technique for quantitative determination of topiramate using liquid chromatography-tandem mass spectrometry. |
PubMed:Intravenous topiramate: comparison of pharmacokinetics and safety with the oral formulation in healthy volunteers. |
PubMed:New and emerging pharmacologic therapies for type 2 diabetes, dyslipidemia, and obesity. |
PubMed:Evaluation of appetite-stimulating hormones in prepubertal children with epilepsy during topiramate treatment. |
PubMed:Two new drugs approved for obesity. |
PubMed:The FDA's assessment of two drugs for chronic weight management. |
PubMed:Current pharmacotherapy options for bulimia nervosa and binge eating disorder. |
PubMed:Topiramate treatment improves hypothalamic insulin and leptin signaling and action and reduces obesity in mice. |
PubMed:Lemons for obesity. |
PubMed:Role of orexin-1 receptor mechanisms on compulsive food consumption in a model of binge eating in female rats. |
PubMed:Review of the pharmacotherapy of irritability of autism. |
PubMed:Botulinum toxin A for prophylactic treatment of migraine and tension headaches in adults: a meta-analysis. |
PubMed:Recent advances in the pathophysiology and pharmacological treatment of obesity. |
PubMed:Market watch: Upcoming market catalysts in Q2 2012. |
PubMed:Antiepileptic drugs and suicidality. |
PubMed:Phentermine/topiramate for weight reduction and treatment of adverse metabolic consequences in obesity. |
PubMed:Epilepsy (generalised). |
PubMed:Treatment of night eating syndrome with topiramate: dawn of a new day. |
PubMed:Night eating syndrome: an overview. |
PubMed:Drug treatment of obesity. |
PubMed:Implications of current clinical trials focused on medication overuse and therapeutic prophylaxis. |
PubMed:Comparative pharmacokinetic analysis of USL255, a new once-daily extended-release formulation of topiramate. |
PubMed:Phentermine plus topiramate in the treatment of obesity. |
PubMed:Epilepsy (partial). |
PubMed:GABAergic and glutamatergic modulation in binge eating: therapeutic approach. |
PubMed:Reversal of abnormal eating and drinking behaviour in a frontotemporal lobar degeneration patient using low-dose topiramate. |
PubMed:ACS chemical neuroscience molecule spotlight on Qnexa. |
PubMed:Migraine headache in children. |
PubMed:Are antiepileptic drugs used in the treatment of migraine associated with an increased risk of suicidality? |
PubMed:Current and future drug targets in weight management. |
PubMed:A multi-center double-blind pilot comparison of onabotulinumtoxinA and topiramate for the prophylactic treatment of chronic migraine. |
PubMed:Do antiepileptic drugs increase the risk of suicidality in adult patients with epilepsy?: a critically appraised topic. |
PubMed:Phentermine, topiramate and their combination for the treatment of adiposopathy ('sick fat') and metabolic disease. |
PubMed:Percentage of subjects with no heavy drinking days: evaluation as an efficacy endpoint for alcohol clinical trials. |
PubMed:Market watch: upcoming market catalysts in Q3 2010. |
PubMed:Anticonvulsant medications and the risk of suicide, attempted suicide, or violent death. |
PubMed:A model of binge-like eating behavior in mice that does not require food deprivation or stress. |
PubMed:Pharmacological management of appetite expression in obesity. |
PubMed:Cluster headache. |
PubMed:Epilepsy (partial). |
PubMed:Epilepsy (generalised). |
PubMed:Bulimia nervosa. |
PubMed:Pharmacologic treatment of impulsive aggression with antiepileptic drugs. |
PubMed:Treatment of nocturnal eating disorders. |
PubMed:Migraine headache in children. |
PubMed:Epilepsy. |
PubMed:Trigeminal neuralgia. |
PubMed:Pre-exposure to environmental cues predictive of food availability elicits hypothalamic-pituitary-adrenal axis activation and increases operant responding for food in female rats. |
PubMed:Randomized, double-blind, placebo-controlled study to evaluate the efficacy and safety of topiramate for migraine prevention in pediatric subjects 12 to 17 years of age. |
PubMed:Severe non-anion gap metabolic acidosis induced by topiramate: a case report. |
PubMed:A preclinical model of binge eating elicited by yo-yo dieting and stressful exposure to food: effect of sibutramine, fluoxetine, topiramate, and midazolam. |
PubMed:The state of pharmacotherapy for the treatment of alcohol dependence. |
PubMed:Adjunctive topiramate enhances the risk of hypothermia associated with valproic acid therapy. |
PubMed:Topiramate attenuates the stress-induced increase in alcohol consumption and preference in male C57BL/6J mice. |
PubMed:Neuromodulators for the treatment of headache disorders and fibromyalgia. |
PubMed:Rufinamide: clinical pharmacokinetics and concentration-response relationships in patients with epilepsy. |
PubMed:[Pharmacological review of alcoholic dependence treatment]. |
PubMed:Emerging concepts in the medical and surgical treatment of obesity. |
PubMed:Neuromodulators for migraine prevention. |
PubMed:Topiramate does not alter nicotine or cocaine discrimination in rats. |
PubMed:Cluster headache. |
PubMed:Bulimia nervosa. |
PubMed:Use of low-dose topiramate in substance use disorder and bodyweight control. |
PubMed:Topiramate, nutrition and weight change: a prospective study. |
PubMed:Update on neuropharmacological treatments for alcoholism: scientific basis and clinical findings. |
PubMed:Topiramate moderately reduces the motivation to consume alcohol and has a marked antidepressant effect in rats. |
PubMed:Dramatic weight loss with levetiracetam. |
PubMed:The cycle of migraine: patients' quality of life during and between migraine attacks. |
PubMed:Sleep-related eating disorder in a 29 year-old man: a case report with diagnostic polysomnographic findings. |
PubMed:Pediatric migraine: pharmacologic agents for prophylaxis. |
PubMed:A new look at the second-generation antiepileptic drugs: a decade of experience. |
PubMed:The effect of topiramate on energy balance in obese men: a 6-month double-blind randomized placebo-controlled study with a 6-month open-label extension. |
PubMed:Bipolar disorder. |
PubMed:Essential tremor. |
PubMed:Topiramate reduces ethanol consumption by C57BL/6 mice. |
PubMed:Topiramate for binge-eating disorder associated with obesity. |
PubMed:Visual stimuli are common triggers of migraine and are associated with pattern glare. |
PubMed:The messenger RNA profiles in liver, hypothalamus, white adipose tissue, and skeletal muscle of female Zucker diabetic fatty rats after topiramate treatment. |
PubMed:Choosing the right medication for the treatment of alcoholism. |
PubMed:Excessive weight gain after remission of depression in a schizophrenic patient treated with risperidone: case report. |
PubMed:Obesity: new perspectives and pharmacotherapies. |
PubMed:Drug adjuncts for treating alcohol dependence. |
PubMed:Hypothalamic regulatory pathways and potential obesity treatment targets. |
PubMed:Topiramate for migraine prevention. |
PubMed:Hormonal and metabolic effects of olanzapine and clozapine related to body weight in rodents. |
PubMed:Night eating syndrome : diagnosis, epidemiology and management. |
PubMed:Medications for treating alcohol dependence. |
PubMed:Effectiveness of topiramate in the treatment of pediatric chronic daily headache. |
PubMed:Medications development: successes and challenges. |
PubMed:North American Association for the Study of Obesity annual meeting. |
PubMed:Topiramate ameliorates hyperglycaemia and improves glucose-stimulated insulin release in ZDF rats and db/db mice. |
PubMed:Pharmacological therapies for obesity. |
PubMed:Meta-analysis: pharmacologic treatment of obesity. |
PubMed:Topiramate: a new potential pharmacological treatment for obesity. |
PubMed:Effects of topiramate on ethanol and saccharin consumption and preferences in C57BL/6J mice. |
PubMed:Oxcarbazepine, topiramate, zonisamide, and levetiracetam: potential use in neuropathic pain. |
PubMed:Metabolic acidosis due to topiramate. |
PubMed:Clinical pharmacotherapy for obesity: current drugs and those in advanced development. |
PubMed:Pharmacokinetic interactions of topiramate. |
PubMed:Clinical pharmacokinetics of levetiracetam. |
PubMed:Newer anticonvulsants in the treatment of bipolar disorder. |
PubMed:Adverse ocular drug reactions recently identified by the National Registry of Drug-Induced Ocular Side Effects. |
PubMed:Effects of topiramate in adults with Prader-Willi syndrome. |
PubMed:Efficacy and tolerability of the new antiepileptic drugs I: treatment of new onset epilepsy: report of the Therapeutics and Technology Assessment Subcommittee and Quality Standards Subcommittee of the American Academy of Neurology and the American Epilepsy Society. |
PubMed:Efficacy and tolerability of the new antiepileptic drugs, II: Treatment of refractory epilepsy: report of the TTA and QSS Subcommittees of the American Academy of Neurology and the American Epilepsy Society. |
PubMed:Efficacy and tolerability of the new antiepileptic drugs, I: Treatment of new-onset epilepsy: report of the TTA and QSS Subcommittees of the American Academy of Neurology and the American Epilepsy Society. |
PubMed:New antiepileptic agents. |
PubMed:Additive effects of leptin and topiramate in reducing fat deposition in lean and obese ob/ob mice. |
PubMed:Treatment of bulimia nervosa with topiramate in a randomized, double-blind, placebo-controlled trial, part 2: improvement in psychiatric measures. |
PubMed:Topiramate-associated acute, bilateral, secondary angle-closure glaucoma. |
PubMed:Pharmacokinetics and metabolism of topiramate. |
PubMed:The ideal pharmacokinetic properties of an antiepileptic drug: how close does levetiracetam come? |
PubMed:New antiepileptic drugs. |
PubMed:Clinical pharmacology of topiramate versus lamotrigine versus phenobarbital: comparison of efficacy and side effects using odds ratios. |
PubMed:Angle-closure glaucoma: impact, etiology, diagnosis, and treatment. |
PubMed:Therapeutics in pediatric epilepsy, Part 1: The new antiepileptic drugs and the ketogenic diet. |
PubMed:The role of anticonvulsants in preventive migraine therapy. |
PubMed:Kidney stones, carbonic anhydrase inhibitors, and the ketogenic diet. |
PubMed:Topiramate-associated secondary angle-closure glaucoma: a case series. |
PubMed:Preliminary evaluation of oral anticonvulsant treatment in the quinpirole model of bipolar disorder. |
PubMed:The effects of topiramate and sex hormones on energy balance of male and female rats. |
PubMed:[Is topiramate effective for weight loss in neuroleptic-induced obesity? 2 case reports]. |
PubMed:Lennox-Gastaut treatment. |
PubMed:Epilepsy in Pregnant Women. |
PubMed:Clinical experience with topiramate dosing and serum levels in children 12 years or under with epilepsy. |
PubMed:Topiramate in posttraumatic stress disorder: preliminary clinical observations. |
PubMed:Topiramate reduces energy and fat gains in lean (Fa/?) and obese (fa/fa) Zucker rats. |
PubMed:Effect of topiramate on body weight and body composition of osborne-mendel rats fed a high-fat diet: alterations in hormones, neuropeptide, and uncoupling-protein mRNAs. |
PubMed:Influence of topiramate in the regulation of energy balance. |
PubMed:Clinical pharmacology of topiramate: a review. |
PubMed:Cognitive effects of topiramate, gabapentin, and lamotrigine in healthy young adults. |
PubMed:Does percent reduction in seizure frequency correlate with plasma concentration of anticonvulsant drugs? Experience with four anticonvulsant drugs. |
PubMed:Newer antiepileptic drugs: gabapentin, lamotrigine, felbamate, topiramate and fosphenytoin. |
PubMed:Recent advances in the pharmacotherapy of epilepsy. |
PubMed:Monotherapy trials of new antiepileptic drugs. |
PubMed:Single-dose pharmacokinetics and effect of food on the bioavailability of topiramate, a novel antiepileptic drug. |
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a hypoglycemic agent. Topiramate is an anticonvulsant drug 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, and now most frequently prescribed for, the prevention of migraines. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm; Chemically, topiramate is a sulfamate-substituted monosaccharide, related to fructose, a rather unusual chemical structure for an anticonvulsant. Topiramate is quickly absorbed after oral use. Most of the drug (70%) is excreted in the urine as unchanged drug. The remainder is extensively metabolized by hydroxylation, hydrolysis, and glucuronidation. Six metabolites have been identified in humans, none of which constitutes more than 5% of an administered dose. 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, particularly 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 secondarily generalized tonic-clonic seizures in the kindling model, findings predictive of a broad spectrum of antiseizure activities clinically; 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. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm. In May 2006 the U.S. National Institutes of Health web site clinicaltrials.gov listed several studies sponsored by Ortho-McNeil which propose to examine the use of topiramate on migraine, cluster, and severe headaches within various demographics; Topiramate (brand name: Topamax) is an anticonvulsant drug produced by Ortho-McNeil, a division of Johnson & Topiramate (brand name: Topamax) is an anticonvulsant drug produced by Ortho-McNeil, 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. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm. In May 2006 the U.S. National Institutes of Health web site clinicaltrials.gov listed several studies sponsored by Ortho-McNeil which propose to examine the use of topiramate on migraine, cluster, and severe headaches within various demographics. [HMDB]
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