Carbamazepine chemical structure

Because carbamazepine has a tricyclic chemical structure, it is not recommended to be taken with MAOIs, including 14 days after MAOIs are stopped do not start an MAOl until 2 weeks after discontinuing carbamazepine... 

Chemical/Pharmaceutical/Other Class Synthetic iminostilbene derivative structurally similar to imipramine, a tricyclic antidepressant. While unrelated structurally, carbamazepine shares a similar therapeutic action with phenytoin Chemical Formula C15H12N2O Chemical Structure ... 

A number of compounds bearing different miscellaneous basic chemical structures have been found to possess significant anticonvulsant properties. A few such compounds are dealt with in this section, namely Primidione, Phenacemide, Carbamazepine, Sultiame, Valproic acid, Clonazepam. A. Primidone INN, BAN, USAN,... 

B. In addition, presumably because its chemical structure is similar to that of the tricyclic antidepressant imipramine, acute carbamazepine overdose can cause seizures and cardiac conduction disturbances. 

Fig. 21.5 The chemical structures of the drug carbamazepine and the receptor amino acids phenylalanine and tryptophan...

From the examination of structure-activity relationships, it has been concluded that a phenyl moiety at C-6 as well as a 4-hydroxypiperidine side-chain attached to C-3 of the pyridazine system is essential for anticonvulsant activity in this class of compounds [184], Compounds (54) and (55) have been found to have similar anticonvulsant profiles in animals (mice, rats and baboons) [165, and literature cited therein] and to represent potent broad-spectrum antiepileptic drugs. Their potency with regard to antagonizing seizures (induced by electro-shock or various chemicals) has been compared with standard anticonvulsants like carbamazepine and phenobarbitone [185, 186], A quantitative electroencephalographic analysis of (55) has been published [187]. From in vitro studies it has been concluded that the anticonvulsant activities of these compounds are not mediated by an enhancement of GABAergic transmission or by an interaction with benzodiazepine receptor sites [ 165,186,187], On the other hand, in vivo experiments showed that (54), at anticonvulsant doses, increases the affinity of flunitrazepam for its central receptor site [ 186], Investigations of (54) and (55) in a behavioural test predictive of antianxiety activity revealed a marked difference in the pharmacological profiles of these structurally closely related compounds the dichloro compound SR 41378 (55) has also been found to possess anxiolytic (anticonflict) properties [165],... 

Figure 2.10 Lattice energy versus density plots of the low energy predicted crystal structures of (a) carbamazepine and (b) 10,11-dihydrocarbamazepine. Observed crystal structures are circled. Two structures are labelled DHCBZ form I here, two lattice energy minima are structurally very similar to the reported crystal structure and these probably converge to a single free energy minimum. Adapted from [40] with permission. Copyright 2003 American Chemical Society...

The useful antiepileptic agents belong to several chemical classes. Most of the drugs introduced before 1965 are closely related in structure to phenobarbital, the oldest member of this therapeutic class. These include the hydantoins, phenytoin, mephenytoin, and ethotoin the deoxybarbiturate, primidone the oxazolidine-diones, trimethadione, and paramethadione and the succinimides, ethosuximide, methsuximide, and phensuximide. The agents introduced after 1965 include the benzodiazepines clonazepan and clorazepate, an iminostilbene, carbamazepine, and a branched-chain carboxylic acid, valproic acid. 

---