Cetirizine Alcohol

The CBS reduction has been employed in numerous synthetic applications.16 The cetirizine hydrochloride 32 (Zyrtec) is an effective treatment as a second-generation histamine HI antagonist for a range of allergic diseases. Zyrtec is one of the leading antihistamine drugs, with sales of 1.3 billion in 2004 in the United States alone. Corey and Helal prepared a chiral benzylic alcohol intermediate 34 en route to their enantioselective synthesis of Zyrtec17 (Scheme 4.3m). The asymmetric reduction of the ketone 33 in toluene with catecholborane in... 

Doms M, Vanhulle G, Baelde Y, Coulie P, Dupont P, Rihoux JP. Lack of potentiation by cetirizine of alcohol-induced psychomotor disturbances. Eur J Clin Pharmacol 1988 34(6) 619—23. 

In a comparison of cetirizine and loratadine, cetirizine 10 mg had acute sedative effects and impaired driving performance (65), whereas loratadine had no sedating potential furthermore, there was an additive effect of alcohol and cetirizine but not alcohol and loratadine. However, in a study using a driving simulator cetirizine 10 mg did not affect driving ability (66). In other studies cetirizine 20 mg caused significant sedation, while in one study there was a dose-dependent sedative effect with 10 mg and 20 mg but not 5 mg (67). Pooling the available data (SEDA-16, 163) shows that cetirizine is little more sedative than loratadine and terfenadine. 

Cetirizine is the primary acid metabolite of hydroxyzine, resulting from complete oxidation of the primary alcohol moiety. This compound is zwittcrionic and relatively polar and thus does not penetrate the BBB readily. Before its introduction in the United States, ectiri/ine was one of the most widely prescribed H antihistamines in Europe. It is highly selective in its interaction with various hormonal binding sites and highly potent ( terfenadinc) as well. " - "... 

Cetirizine, the acid metabolite from oxidation of the primary alcohol of the antihistamine hydroxyzine (Fig. 37.15 and Table 37.6), is a widely used antihistamine (38). It has a long duration of action and is highly selective for Hi receptors. No cardiotoxicity has been reported, but some drowsiness occurs. The R-enantiomer of cetirizine, levocetirizine, is marketed in Europe. Levocetirizine has higher affinity than its S-enantiomer for the Hi receptor (>30-fold) and is more slowly dissociated by more than 20-fold from the receptor (39). Thus, the antihistaminic... 

The non-sedating antihistamines seem to cause little or no drowsiness in most patients and the risks if taken alone or with alcohol appear to be minimal or absent. However, the incidence of sedation varies with the non-sedating antihistamine (e.g. sedation appears to be lower with fexofenadine and loratadine than with acrivastine or cetirizine) and with the individual (e.g. women may be more affected than men). Therefore, patients should be advised to be alert to the possibility of drowsiness if they have not taken the drug before. Any drowsiness would be apparent after the first few doses. The patient information leaflets for acrivastine and cetirizine suggest avoidance of alcohol or excessive amounts of alcohol, and caution is advised with levocetirizine. ... 

Barbanoj MJ, Garcia-Gea C, Antonijoan R, Izquierdo I, Dc ado E, Perez I, Solans A, Jane F. Evaluation of the cognitive, psychomotor and irharmacokinetic profiles of rupatadiine, hydroxyzine and cetirizine, in combination with alcohol, in healthy volunteers. Hum Psychop-harmacol(2006)2, 13-26... 

Three patients experienced application site erythema following the consumption of alcohol after using topical tacrolimus or pimecrolimus for the treatment of facial dermatoses. Two of the patients then participated in a double-blind, controlled evaluation of the reaction. Both patients consumed alcohol (240 mL of red or white wine) without experiencing flushing, but following tacrolimus or pimecrolimus application, they experienced moderate or severe facial flushing (limited to the area of application) 5 to 10 minutes after alcohol consumption. The intensity of the erythema was sharply reduced after taking aspirin 325 mg twice daily for 3 days before alcohol consumption, but cetirizine 10 mg daily with cime-tidine 400 mg twice daily for 3 days appeared to have little effect. ... 

This was her first exposure to cetirizine or any other piperazine derivative, and on recovery she reported no previous history of allergic drug reactions or concomitant use of any other medication or alcohol [3 ]. Although fixed drug eruptions have been previously reported with both cetirizine and levocetirizine [SEDA-31, 30] anaphylaxis caused by systemic antihistamines is very rare, particularly in the absence of known previous exposure. The authors speculated that the potential antigenic nature of the piperazine ring may have been a factor [4 ]. 

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