Description
Meclizine is a histamine H
1 receptor antagonist (K
i = 250 nM). Pretreatment with meclizine (2.5-30 mg/kg, i.p.) reduces ovalbumin-induced mast cell degranulation, edema, and leukocyte influx in rat lung. Formulations containing meclizine have been used in the treatment of motion sickness and vertigo.
Chemical Properties
White or yellowish-white, slightly hygroscopic, crystalline powder.
Originator
Antivert,Roerig,US,1957
Uses
Meclizine Dihydrochloride is a histamine H1 receptor antagonist with antiemetic properties. Meclizine Dihydrochloride is a research product for neuroscience. This compound may exhibit neuroprotective properties.
Uses
cholinergic, diagnostic aid
Uses
Antiemetic;Histamine antagonist
Manufacturing Process
32.3 g of 1-p-chlorobenzhydryl-4-benzyl-piperazine, dissolved in 300 cm3 of alcohol are heated in an autoclave vessel, in the presence of Raney nickel, under a pressure of 100 kg H2, at about 150°C for 6 hours. The catalyst is filtered, the solvent is evaporated and the residue is fractionated under a high vacuum. p-Chlorobenzylhydryl-piperazine (BP 180° to 185°C/1 mm Hg) is isolated with a yield of 75%. Then finely ground NaNH2 is added. The mixture is heated under reflux for 1 hour, the mass is cooled and a molar equivalent of m-methyl benzyl chloride is added.
The solvent is evaporated and the residue is dissolved in chloroform. This
solution is washed with a saturated solution of K2CO3 and dried on K2CO3. The
solvent is evaporated and the residue is distilled under high vacuum. The
product of the condensation distills near 230°C at 2 mm Hg pressure and the
corresponding dihydrochloride melts at 217° to 224°C.
brand name
Antivert (Pfizer).
Therapeutic Function
Antinauseant
Biochem/physiol Actions
Meclizine has the ability to increase glycolysis and decrease cellular ATP levels in media that has glucose and galactose. It guards the kidney against ischemia-reperfusion injury. Meclizine is considered as an anti-nausea and anti-dizziness drug, was identified in a ′nutrient-sensitized′ chemical screen. In human, it acts as an agonist of pregnane X receptor (PXR). It enhances the expression of CYP3A4 (cytochrome P450 3A4) mRNA and reduces CYP3A-catalyzed testosterone 6β-hydroxylation in primary cultures of human hepatocytes.
Safety Profile
Moderately toxic by
ingestion and intraperitoneal routes. An
experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits very toxic fumes of
Cland NOx.
Solubility in organics
Meclizine dihydrochloride is readily soluble in chloroform and pyridine, slightly soluble in dilute acids and ethanol, and insoluble in water or ether.
