Topiramate

Last updated

Topiramate
Topiramate structure.svg
Topiramate 3D.png
Clinical data
Trade names Topamax, Trokendi XR, Qudexy XR, others
Other namesTopiramic acid
AHFS/Drugs.com Monograph
MedlinePlus a697012
License data
Pregnancy
category
  • AU:D
Routes of
administration 		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 80%
Protein binding 13–17%; 15–41%
Metabolism Liver (20–30%)
Elimination half-life 21 hours
Excretion Urine (70–80%)
Identifiers
  • 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard 100.129.713 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H21NO8S
Molar mass 339.36 g·mol−1
3D model (JSmol)
  • O=S(=O)(OC[C@@]21OC(O[C@H]1[C@@H]3OC(O[C@@H]3CO2)(C)C)(C)C)N
  • 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 Yes check.svgY
  • Key:KJADKKWYZYXHBB-XBWDGYHZSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Topiramate, sold under the brand name Topamax among others, is a medication used to treat epilepsy and prevent migraines. [9] It has also been used in alcohol dependence and essential tremor. [9] For epilepsy this includes treatment for generalized or focal seizures. [10] It is taken orally (by mouth). [9]

Contents

Common side effects include tingling, feeling tired, loss of appetite, abdominal pain, weight loss, [11] and decreased cognitive function such as trouble concentrating. [9] [10] Serious side effects may include suicide, increased ammonia levels resulting in encephalopathy, and kidney stones. [9] Topiramate can cause birth defects including cleft lip and palate. [12] Risk/benefit should be carefully discussed with the full treatment team. Topiramate is considered "probably compatible" with lactation and is not contraindicated in breastfeeding, though monitoring of the infant for diarrhea or poor weight gain may be considered. [13] [14] The mechanism of action is unclear. [9]

Topiramate was approved for medical use in the United States in 1996. [9] It is available as a generic medication. [10] [15] [16] In 2021, it was the 66th most commonly prescribed medication in the United States, with more than 10 million prescriptions. [17] [18]

Medical uses

A package of topiramate 25mg from Norway Topimax 25mg.jpg
A package of topiramate 25mg from Norway

Topiramate is used to treat epilepsy in children and adults, and it was originally used as an anticonvulsant. [19] In children, it is indicated for the treatment of Lennox-Gastaut syndrome, a disorder that causes seizures and developmental delay. It is most frequently prescribed for the prevention of migraines [19] as it decreases the frequency of attacks. [20] [21] Topiramate is used to treat medication overuse headache and is recommended by the European Federation of Neurological Societies as one of the few medications showing effectiveness for this indication. [22]

Pain

A 2018 review found topiramate of no use in chronic low back pain. [23] Topiramate has not been shown to work as a pain medicine in diabetic neuropathy, the only neuropathic condition in which it has been adequately tested. [24]

Other

One common off-label use for topiramate is in the treatment of bipolar disorder. [25] [26] [27] A review published in 2010 suggested a benefit of topiramate in the treatment of symptoms of borderline personality disorder, however the authors noted that this was based only on one randomized controlled trial and requires replication. [28]

Topiramate has been used as a treatment for alcoholism. [29] The U.S. Veterans Affairs and Department of Defense 2015 guidelines on substance use disorders list topiramate as a "strong for" in its recommendations for alcohol use disorder. [30]

Other uses include treatment of obesity, [31] [32] binge eating disorder, [33] and off-setting weight gain induced by taking antipsychotic medications. [34] [35] In 2012, the combination of phentermine/topiramate was approved in the United States for weight loss.

Adverse effects

People taking topiramate should be aware of the following risks:

Frequency

Adverse effects by incidence: [40] [41] [42] [43]

Very common (>10% incidence) adverse effects include:

Rarely, the inhibition of carbonic anhydrase may be strong enough to cause metabolic acidosis of clinical importance. [44]

The U.S. Food and Drug Administration (FDA) has notified prescribers that topiramate can cause acute myopia and secondary angle closure glaucoma in a small subset of people who take topiramate regularly. [45] The symptoms, which typically begin in the first month of use, include blurred vision and eye pain. Discontinuation of topiramate may halt the progression of the ocular damage and may reverse the visual impairment.

Preliminary data suggests that, as with several other anti-epileptic drugs, topiramate carries an increased risk of congenital malformations. [46] This might be particularly important for women who take topiramate to prevent migraine attacks. In March 2011, the FDA notified healthcare professionals and patients of an increased risk of development of cleft lip and/or cleft palate (oral clefts) in infants born to women treated with Topamax (topiramate) during pregnancy and placed it in Pregnancy Category D. [38]

Cognitive and word-finding difficulties, as they may occur in some patients, may respond to piracetam. [47] [48]

Topiramate has been associated with a statistically significant increase in suicidality, [49] and "suicidal thoughts or actions" is now listed as one of the possible side effects of the drug "in a very small number of people, about 1 in 500." [36] [50]

Overdose

Symptoms of acute and acute on chronic exposure to topiramate range from asymptomatic to status epilepticus, including in patients with no seizure history. [51] [52] In children, overdose may also result in hallucinations. [52] Topiramate has been deemed the primary substance that led to fatal overdoses in cases that were complicated by polydrug exposure. [53] The most common signs of overdose are dilated pupils, somnolence, dizziness, psychomotor agitation, and abnormal, uncoordinated body movements. [51] [52] [53]

Interactions

Topiramate has many drug-drug interactions. Some of the most common are listed below:

Pharmacology

Chair-style representation of skeletal formula Topiramate (chair style).svg
Chair-style representation of skeletal formula

The topiramate molecule is a sulfamate modified sugar, more specifically, fructose diacetonide, an unusual chemical structure for a pharmaceutical.

Topiramate is quickly absorbed after oral use. It has a half life of 21 hours and a steady state of the drug is reached in 4 days in patients with normal renal function. [56] Most of the drug (70%) is excreted in the urine unchanged. 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.

Several cellular targets have been proposed to be relevant to the therapeutic activity of topiramate. [57] These include (1) voltage-gated sodium channels; (2) high-voltage-activated calcium channels; (3) GABA-A receptors; (4) AMPA/kainate receptors; and (5) carbonic anhydrase isoenzymes. There is evidence that topiramate may alter the activity of its targets by modifying their phosphorylation state instead of by a direct action. [58] The effect on sodium channels could be of particular relevance for seizure protection. Although topiramate does inhibit high-voltage-activated calcium channels, the relevance to clinical activity is uncertain. Effects on specific GABA-A receptor isoforms could also contribute to the antiseizure activity of the drug. Topiramate selectively inhibits cytosolic (type II) and membrane associated (type IV) forms of carbonic anhydrase. The action on carbonic anhydrase isoenzymes may contribute to the drug's side-effects, including its propensity to cause metabolic acidosis and calcium phosphate kidney stones.

Topiramate inhibits maximal seizure activity in electroconvulsive therapy and in pentylenetetrazol-induced seizures as well as partial and secondarily generalized tonic-clonic seizures in the kindling model, findings predictive of a broad spectrum of activities clinically. Its action on mitochondrial permeability transition pores has been proposed as a mechanism. [59]

While many anticonvulsants have been associated with apoptosis in young animals, animal experiments have found that topiramate is one of the very few anticonvulsants [see: levetiracetam, carbamazepine, lamotrigine] that do not induce apoptosis in young animals at doses needed to produce an anticonvulsant effect. [60]

Detection in body fluids

Blood, serum, or plasma topiramate concentrations may be measured using immunoassay or chromatographic methods to monitor therapy, confirm a diagnosis of poisoning in hospitalized patients, or to assist in a medicolegal death investigation. Plasma levels are usually less than 10 mg/L during therapeutic administration, but can range from 10 to 150 mg/L in overdose victims. [61] [62] [63]

History

Topiramate was discovered in 1979 by Bruce E. Maryanoff and Joseph F. Gardocki during their research work at McNeil Pharmaceuticals. [64] [65] Topiramate was first sold in 1996. [66] Mylan Pharmaceuticals was granted final approval by the FDA for the sale of generic topiramate in the United States and the generic version was made available in September 2006. [67] The last patent for topiramate in the U.S. was for use in children and expired on 28 February 2009. [68]

Research

Topiramate is being studied as a potential treatment for post traumatic stress disorder. [69]

There is some evidence for the use of topiramate in the management of cravings related to withdrawal from dextromethorphan. [70]

A 2023 systematic review of seizure treatment for infants aged 1 to 36 months identified three studies that evaluated the use of topiramate. Though its adverse effects including upper respiratory tract infection and loss of appetite were rarely severe enough for the medication to be discontinued in this age group, its effectiveness in reducing seizures was inconclusive. The available research suffers from small sample sizes, inconsistent findings, and inadequate comparison groups. [71]

Related Research Articles

<span class="mw-page-title-main">Valproate</span> Medication used for epilepsy, bipolar disorder and migraine

Valproate are medications primarily used to treat epilepsy and bipolar disorder and prevent migraine headaches. They are useful for the prevention of seizures in those with absence seizures, partial seizures, and generalized seizures. They can be given intravenously or by mouth, and the tablet forms exist in both long- and short-acting formulations.

Anticonvulsants are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of bipolar disorder and borderline personality disorder, since many seem to act as mood stabilizers, and for the treatment of neuropathic pain. Anticonvulsants suppress the excessive rapid firing of neurons during seizures. Anticonvulsants also prevent the spread of the seizure within the brain.

<span class="mw-page-title-main">Diazepam</span> Benzodiazepine sedative

Diazepam, first marketed as Valium, is a medicine of the benzodiazepine family that acts as an anxiolytic. It is commonly used to treat a range of conditions, including anxiety, seizures, alcohol withdrawal syndrome, muscle spasms, insomnia, and restless legs syndrome. It may also be used to cause memory loss during certain medical procedures. It can be taken orally, as a suppository inserted into the rectum, intramuscularly, intravenously or used as a nasal spray. When injected intravenously, effects begin in one to five minutes and last up to an hour. Orally, effects begin after 15 to 60 minutes.

<span class="mw-page-title-main">Lamotrigine</span> Medication used for bipolar disorder, epilepsy, & many seizure disorders

Lamotrigine, sold under the brand name Lamictal among others, is a medication used to treat epilepsy and stabilize mood in bipolar disorder. For epilepsy, this includes focal seizures, tonic-clonic seizures, and seizures in Lennox-Gastaut syndrome. In bipolar disorder, lamotrigine has not been shown to reliably treat acute depression for all groups except the severely depressed group; but for patients with bipolar disorder who are not currently symptomatic, it appears to be effective in reducing the risk of future episodes of depression.

<span class="mw-page-title-main">Oxcarbazepine</span> Anticonvulsant medication

Oxcarbazepine, sold under the brand name Trileptal among others, is a medication used to treat epilepsy. For epilepsy it is used for both focal seizures and generalized seizures. It has been used both alone and as add-on therapy in people with bipolar disorder who have had no success with other treatments. It is taken by mouth.

<span class="mw-page-title-main">Levetiracetam</span> Medication

Levetiracetam, sold under the brand name Keppra among others, is a medication used to treat epilepsy. It is used for partial-onset, myoclonic, or tonic–clonic seizures and is taken either by mouth as an immediate or extended release formulation or by injection into a vein.

<span class="mw-page-title-main">Clonazepam</span> Benzodiazepine medication

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<span class="mw-page-title-main">Tiagabine</span> Anticonvulsant medication

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<span class="mw-page-title-main">Primidone</span> Barbiturate medication used to treat seizures and tremors

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<span class="mw-page-title-main">Clobazam</span> Benzodiazepine class medication

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<span class="mw-page-title-main">Felbamate</span> Chemical compound

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<span class="mw-page-title-main">JNJ-26489112</span> Chemical compound

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