Oxcarbazepine
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Oxcarbazepine
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Systematic (IUPAC) name | |
10,11-Dihydro-10-oxo-5 H -dibenz(b,f)azepine-5-carboxamide | |
Identifiers | |
CAS number | |
ATC code | N03 |
PubChem | |
DrugBank | |
Chemical data | |
Formula | C15H12N2O2 |
Mol. mass | 252.268 g/mol |
Pharmacokinetic data | |
Bioavailability | > 95% |
Protein binding | ? |
Metabolism | Liver (Cytosolic Enzymes & Glucuronic Acid) |
Half life | 1-5 hours (healthy adults) |
Excretion | Renal |
Therapeutic considerations | |
Pregnancy cat. |
C(US) |
Legal status | |
Routes | Oral (Tablets or Suspension) |
Oxcarbazepine (marketed as Trileptal® by Novartis) is an anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy and bipolar disorder.
Oxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom on the dibenzazepine ring. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat the same conditions. Oxcarbazepine has recently been found associated with a greater enhancement in mood and reduction in anxiety symptoms than other drugs employed to treat epilepsy (Mazza, Marca, Di Nicola et al.,Eplepsy Behav. 14 Feb. 2007).
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[edit] Side effects
Oxcarbazepine occasionally causes fatigue, nausea, vomiting, headache, dizziness, drowsiness, and blurred or double vision. It can cause hyponatremia, so blood sodium levels should be tested if the patient complains of severe fatigue. Some of these side effects (such as headache) are more pronounced shortly after a dose is taken and tend to fade with the passage of time (generally 60 to 90 minutes). Along with these side effects, pseudo side effects have also been that of desires for salty foods (such as potato chips).
[edit] History
First synthesized in 1966, it was approved for use as an anticonvulsant in Denmark in 1990. It was approved in Spain in 1993, in Portugal in 1997, and eventually for all other EU countries in 1999. It was approved in the US in 2000.
[edit] Other information
Oxcarbazapine may cause oral hormonal contraceptives to be less effective.
[edit] References
- ChemicalLand21.com: Oxcarbazepine
- Trileptal Story
- Trileptal.com(Novartis)
- Prescribing Information(PDF)
[edit] External links
- Explanatory article
- Diagram illustrating the chief difference between oxcarbazepine and carbamazepine
- RxList entry
- http://www.psycheducation.org/depression/meds/moodstabilizers.htm
- http://www.psycheducation.org/depression/meds/trileptal.htm
- DrugBank entry
Barbiturates: Barbexaclone, Metharbital, Methylphenobarbital, Phenobarbital, Primidone
Hydantoins: Ethotoin, Fosphenytoin, Mephenytoin, Phenytoin
Oxazolidinediones: Ethadione, Paramethadione, Trimethadione
Succinimides: Ethosuximide, Mesuximide, Phensuximide
Benzodiazepines: Clobazam, Clonazepam, Clorazepate, Diazepam, Lorazepam, Midazolam, Nitrazepam, Temazepam
Carboxamides: Carbamazepine, Oxcarbazepine, Rufinamide Fatty acid derivatives: Valpromide, Valnoctamide
Carboxylic acids: Valproic acid (Sodium valproate & Valproate semisodium), Tiagabine -- GABA analogs: Gabapentin, Pregabalin, Progabide, Vigabatrin
Others:- Monosaccharides: Topiramate -- Aromatic allylic alcohols: Stiripentol -- Ureas: Phenacemide, Pheneturide -- Phenyltriazines: Lamotrigine
Carbamates: Emylcamate, Felbamate, Meprobamate -- Pyrrolidines: Brivaracetam, Levetiracetam, Nefiracetam, Seletracetam
Sulfa drugs: Acetazolamide, Ethoxzolamide, Sultiame, Zonisamide -- Propionates: Beclamide -- Aldehydes: Paraldehyde -- Bromides: Potassium bromide, Sodium bromide