Chemical Structure:
C19H35NO2 · HCl
Mechanism of Action:
Dicyclomine is an anticholinergic drug that blocks the action of acetylcholine at muscarinic receptors in the smooth muscle of the gastrointestinal tract.
Structure-Activity Relationship (SAR) of Dicyclomine Hydrochloride:
1.Tertiary Amine:
Dicyclomine contains a tertiary amine, which is essential for its antimuscarinic activity.
This feature allows it to cross membranes more easily than quaternary ammonium compounds, affecting its distribution and activity.
2.Cyclic Structure:
The bicyclic structure is crucial for the drug's spasmolytic activity. Alterations in the cyclic structure can significantly affect the drug's efficacy and selectivity for muscarinic receptors.
3.Ester Linkage:
Dicyclomine has an ester linkage, which is a common feature in many antimuscarinic agents.
This part of the molecule plays a role in binding to the muscarinic receptor.
4.Aromatic Ring:
The presence of an aromatic ring is important for the molecule's pharmacological activity, contributing to its binding affinity and overall efficacy.
Synthesis of Dicyclomine Hydrochloride (Chemical Reaction):
The synthesis of Dicyclomine Hydrochloride typically involves the following steps:
1.Starting with Cyclohexanone:
The synthesis often begins with cyclohexanone, which is converted into a cyclohexene derivative.
2.Formation of the Bicyclic Structure:
Cyclohexene derivative + Diethylamine → Bicyclic Intermediate
3.Introduction of Ester and Aromatic Groups:
Bicyclic Intermediate + Aromatic components → Dicyclomine
4.Formation of Hydrochloride Salt:
Dicyclomine+Hydrochloric Acid→Dicyclomine Hydrochloride
In this synthesis, the key steps involve forming the bicyclic structure integral to dicyclomine's activity, followed by the introduction of ester and aromatic groups to complete the active molecule's structure.
Finally, the hydrochloride salt is formed to improve the drug's stability and solubility.
Uses:
It is used to treat functional bowel or irritable bowel syndrome.
Side Effects:
Side effects include dry mouth, blurred vision, confusion, agitation, and constipation.