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HOME >> API >> API List1 >> Clomipramine HCL >> Pharmalogy

Formula C19H23ClN2

Clomipramine CAS number 17321-77-6

Clomipramine is the 3-chloro derivative of imipramine. Clomipramine is a strong, but not completely selective serotonin reuptake inhibitor (SSRI), as the primary active metabolite desmethylclomipramine acts preferably as norepinephrine reuptake inhibitor. Other hydroxy-metabolites are also active. α1 receptor blockage and β receptor downregulation as well as postsynaptic antagonism on histamine H1 receptors and dopamine receptors have been noted.

As with other tricyclics, downregulation of NMDA receptors may also account for its effects.

Clomipramine has the disadvantage of a higher incidence of seizures than seen with other tricyclic antidepressants (up to a dose of 250 mg daily in 0,5 %, more than 300 mg in 2 %).

Clomipramine is a tricyclic agent with both antidepressant and antiobsessional properties. Like other tricyclics, clomipramine inhibits norepinephrine and serotonin uptake into central nerve terminals, possibly by blocking the membrane-pump of neurons, thereby increasing the concentration of transmitter monoamines at receptor sites. Clomipramine is presumed to influence depression and obsessive and compulsive behaviour through its effects on serotonergic neurotransmission. The actual neurochemical mechanism is unknown, but clomipramine's capacity to inhibit serotonin reuptake is thought to be important. Clomipramine appears to have a mild sedative effect which may be helpful in alleviating the anxiety component often accompanying depression.

As with other tricyclic compounds, clomipramine possesses anticholinergic properties which are responsible for some of its side effects. It also has weak antihistamine and antiserotonin properties, lowers the convulsive threshold, potentiates the effect of norepinephrine and other drugs acting on the CNS, has a quinidine-like effect on the heart and may impair cardiac conduction.

The action of clomipramine on the human EEG is one of desynchronization. It causes a persistent increase in the frequency of shifts into stage I sleep and produces marked reduction or suppression of rapid eye movement sleep (REM or paradoxical sleep) with partial recovery within 3 to 4 weeks and a rebound after drug withdrawal which appears to last approximately the same time. In normal human volunteers tricyclic antidepressants tend to produce a sedative effect accompanied by atropine-like symptoms and may produce some difficulty in concentrating and thinking.

Absorption is rapid and complete after oral administration in man. Plasma levels usually peak 2 hours after dosage but much individual variation occurs. The plasma half-life after a single oral dose is approximately 21 hours. After 28 days of oral administration to patients in a daily dosage of 75 mg, plasma concentrations of clomipramine ranged from 17 to 70 ng/mL (mean=35.7 ng/mL). The concentration of the active metabolite, desmethylclomipramine, was about twice as high.

Binding to serum proteins at 96 to 97% is very high and is practically concentration-independent within the therapeutic range. Clomipramine has a volume of distribution of approximately 12 L/kg bodyweight.

Clomipramine is extensively metabolized in the body with hydroxylation, demethylation and N-oxidation being the quantitatively more important routes of metabolism.

Owing to the lower clearance of clomipramine in plasma, elderly patients require lower doses of clomipramine than patients in younger age groups.

As expected, the metabolites of clomipramine are quite similar to those of imipramine, all retaining the benzazepine structure. Two-thirds of clomipramine is excreted in the form of water-soluble conjugates in the urine and approximately one-third in the feces. After a 25 mg radiolabelled dose of clomipramine in 2 subjects, the urinary recoveries of clomipramine and desmethylclomipramine were about 2% and 0.5% of the total radioactivity, respectively.

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