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Carbamazepine chemical structure
| CAS number |
| ATC code |
| PubChem |
| DrugBank |
|Molecular weight||236.269 g/mol|
|Metabolism||hepatic CYP3A4 to active epoxide form|
|Elimination half-life||25-65 hours|
|Excretion||2-3% excreted unchanged in urine|
|Routes of administration||oral|
Carbamazepine (sold under the brand-names Biston, Calepsin, Carbatrol, Epitol, Equetro, Finlepsin, Sirtal, Stazepine, Tegretol, Telesmin, Timonil, sometimes abbreviated CBZ) is an anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy and bipolar disorder. It is also used to treat schizophrenia and trigeminal neuralgia.
Carbamazepine and its derivatives' mechanism of action is relatively well understood. Voltage gated sodium channels are the molecular pores that allow brain cells (neurons) to generate action potentials, the electrical event that allows neurons to communicate over long distances. After the sodium channels open, to start the action potential, they inactivate, essentially closing the channel. Carbamazepine stabilizes the inactivated state of sodium channels, meaning that fewer sodium channels are available to open, making brain cells less excitable.
Carbamazepine renders birth control pills ineffective because it is an enzyme inducer of the cytochrome P450 system which metabolises the oral contraceptive, leaving less active contraceptive in the plasma.
Less common side effects include, cardiac arrythmias, blurry or double vision and/or the temporary or mild loss of blood cells or platelets. In rare cases the latter can be life-threatening if unnoticed, so frequent blood tests are required during the first few months' use, followed by three or four tests per year. In the UK testing would be less frequent in long-term use, typically once every year or two. Underactivity of the thyroid gland may be provoked, so thyroid function tests are advisable every year or two.
Small reductions in white cell count and serum sodium are common.
There are also reports of a bizarre auditory side effect, whereby patients perceive musical notes about a semitone lower than their actual pitch (so middle C would be heard as the note B3 just below it, etc).
Oxcarbazepine, a derivative of carbamazepine, has fewer and less serious side effects.
Carbamazepine may aggravate juvenile myoclonic epilepsy, so it is important to mention any history of jerking, especially in the morning, before starting to take this drug.
Carbamazepine was discovered by chemist Walter Schindler at J.R. Geigy AG (now part of Novartis) in Basel, Switzerland, in 1953. Schindler then synthesized the drug in 1960, before its anti-epileptic properties had been discovered.
If taken as meant as drug, side effects include double vision, euphoric feeling, drowsiness, and other mild side effects.
- W Schindler and F Häfliger, Über derivate des iminodibenzyls, Helvetica Chimica Acta 1954, 37:472-483
- ^ M. Ucar et al (2004). Carbamazepine markedly reduces serum concentrations of simvastatin and simvastatin acid. Eur J Clin Pharmacol 59: 879–882.
- Carbatrol website
- Equetro website
- TA warning
- Carbamazepine overview from PsychEducation.org
- U.S. Patent 2,948,718, August 1960
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