Dibenzocycloheptenes And Dibenzocycloheptanes

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The dibenzocycloheptene and dibenzocycloheptane antihis-tamines may be regarded as phenothiazine analogs in which the sulfur atom has been replaced by an isosteric vinyl group (cyproheptadine) or a saturated ethyl bridge (azatadine), and the ring nitrogen has been replaced by an sp2 carbon atom (Fig. 23.12). The two members of this series are closely related in structure; azatadine is an aza (pyridyl) isostere of cyproheptadine in which the 10,11-double bond is reduced. These agents are potent antihistamines with moderate sedation and anticholinergic potential, and little antiemetic activity (Table 23.2).

Cyproheptadine Hydrochloride. Cyproheptadine hydrochloride, 4-(5H-dibenzo-[a,d]-cyclohepten-5-yli-dine)-1-methylpiperidine hydrochloride sesquihydrate (Periactin), is slightly soluble in water and sparingly soluble in alcohol.

Cyproheptadine possesses both antihistamine and anti-serotonin activity and is used as an antipruritic agent. It is indicated for the treatment of hypersensitivity reactions, perennial, and seasonal allergic rhinitis; vasomotor rhinitis; allergic conjunctivitis, uncomplicated allergic skin manifestations of urticaria and angioedema; amelioration of allergic reactions to blood or plasma; and cold urticaria. It is also used off-label for nightmares associated with posttraumatic stress disorder (PTSD), prevention of migraine, suppression of vascular headaches, and appetite stimulation. Sedation is the most prominent side effect, and this is usually brief, disappearing after 3 or 4 days of treatment.

Dosage forms: Tablets (4 mg) and syrup (2 mg/5 mL) Usual adult dose: Oral, 4 mg 3 or 4 times a day

Azatadine Maleate. Azatadine maleate, 6,11-dihydro-11-(l-methyl-4-piperidylidene)-5H-benzo-[5,6]cyclo-

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