Chemical Structure:
C15H12N2O
Mechanism of Action:
Carbamazepine works by inhibiting voltage-gated sodium channels, which decreases the release of glutamate, the body's main excitatory neurotransmitter.
Structure-Activity Relationship (SAR) of Carbamazepine:
1.Tricyclic Structure:
Carbamazepine features a tricyclic structure, similar to the tricyclic antidepressants, which is crucial for its activity. This structure includes an iminostilbene core, a central ring connected to two benzene rings.
2.Carbamoyl Group:
The carbamoyl group at the 5th position of the tricyclic structure is essential for anticonvulsant activity. This feature distinguishes it from the related tricyclic antidepressants.
3.Double Bond:
The double bond in the central ring is crucial for the drug's activity. Modifications to this double bond can significantly affect the drug's efficacy and potency.
4.Lipophilicity:
The overall lipophilicity of the molecule, contributed by the tricyclic structure, affects its pharmacokinetic properties, including absorption, distribution, and brain penetration, which are important for its antiepileptic effects.
Synthesis of Carbamazepine (Chemical Reaction):
The synthesis of Carbamazepine typically involves the following simplified reaction:
1.Schotten-Baumann Reaction:
Iminostilbene + Carbamoyl chloride → (base) → Carbamazepine
In this reaction, iminostilbene is reacted with carbamoyl chloride in the presence of a base.
The base typically used is an organic or inorganic base that facilitates the nucleophilic attack of the amine group on the carbamoyl chloride, leading to the formation of Carbamazepine.
Uses:
It's used as an anticonvulsant to control seizures, and also for the treatment of certain types of neuropathic pain.
Side Effects:
It can cause dizziness, drowsiness, and, in more serious cases, liver damage and blood dyscrasias.