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QuickView for Topiramate (compound)

Name: topiramate
PubChem Compound ID: 10664802
Molecular formula: C12H21NO8S
Molecular weight: 339.363 g/mol
Name: topiramate
Name (isomeric): DB00273
Drug Type: small molecule
Topiramatum [INN-Latin]; Tipiramato [Spanish]; Topiramic acid; Tipiramate [French]; topiramate tablet; Topiramato [INN-Spanish]
Brand: Topamax Sprinkle, Topamax
Category: Anti-Obesity Agents, Neuroprotective Agents, Anticonvulsants
CAS number: 97240-79-4
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.
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 inh...
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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...
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Absorption: Rapid with pleak plasma concentrations occurring after 2 hours and a bioavailability of 80%.
Protein binding: 15-41% (over the blood concentration range of 0.5 - 250 mg/mL).
Biotransformation: 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.
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
Clearance: Oral plasma cl=20 - 30 mL/min [in humans following oral administration]
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
Drug interaction:
PhenytoinIncreased phenytoin/decreased topiramate
AcetazolamideAdditive renal carbonic anhydrase inhibition may occur increasing the risk of crystaluria and renal calculi. Increased risk of nephrolithiasis. Consider altnerate therapy.
FosphenytoinIncreased phenytoin/decreased topiramate
TobramycinIncreased risk of nephrotoxicity
MaravirocTopiramate, a CYP3A4 inducer, may decrease the serum concentration of Maraviroc by increasing Maraviroc metabolism and clearance. A dose adjustment of Maraviroc may be required. Monitor for changes in Maraviroc therapeutic and adverse effects if Topiramate is initiated, discontinued or dose changed.
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