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Titolo:
Ionic partition diagram of the zwitterionic antihistamine cetirizine
Autore:
Bouchard, G; Pagliara, A; van Balen, GP; Carrupt, PA; Testa, B; Gobry, V; Girault, HH; Caron, G; Ermondi, G;
Indirizzi:
Univ Lausanne, Inst Chim, BEP, CH-1015 Lausanne, Switzerland Univ Lausanne Lausanne Switzerland CH-1015 CH-1015 Lausanne, Switzerland Ecole Polytech Fed Lausanne, Lab Electrochim, CH-1015 Lausanne, Switzerland Ecole Polytech Fed Lausanne Lausanne Switzerland CH-1015 ne, Switzerland Univ Turin, Dipartimento Sci & Technol Farmaco, I-10125 Turin, Italy Univ Turin Turin Italy I-10125 i & Technol Farmaco, I-10125 Turin, Italy Univ Piemonte Orientale, DISCAFF, I-28100 Novara, Italy Univ Piemonte Orientale Novara Italy I-28100 CAFF, I-28100 Novara, Italy
Titolo Testata:
HELVETICA CHIMICA ACTA
fascicolo: 2, volume: 84, anno: 2001,
pagine: 375 - 387
SICI:
0018-019X(2001)84:2<375:IPDOTZ>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
IMMISCIBLE ELECTROLYTE-SOLUTIONS; METRIC LOG-P; MULTIPROTIC SUBSTANCES; COEFFICIENTS; LIPOPHILICITY; INTERFACE; BEHAVIOR; DIFFERENCE; IONIZATION; MECHANISM;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
29
Recensione:
Indirizzi per estratti:
Indirizzo: Testa, B Univ Lausanne, Inst Chim, BEP, CH-1015 Lausanne, Switzerland UnivLausanne Lausanne Switzerland CH-1015 ausanne, Switzerland
Citazione:
G. Bouchard et al., "Ionic partition diagram of the zwitterionic antihistamine cetirizine", HELV CHIM A, 84(2), 2001, pp. 375-387

Abstract

A recent analysis of the lipophilicity profile of cetirizine in the octanol/water and dodecane/water systems revealed a partial intramolecular chargeneutralization that can partly explain why cetirizine has pharmacokinetic properties differing from those of first-generation antihistamines such as hydroxyzine. As conformational changes are the principal driving force for this intramolecular effect, the present study deals with the partitioning of cetirizine and hydroxyzine in an apolar medium well-suited to reveal intramolecular interactions, namely the 1,2-dichloroethane/water system. The lipophilicity of the different electrical forms of cetirizine and hydroxyzinewas studied by two-phase titrimetry and cyclic voltammetry. The differences in lipophilicity between the dicationic, monocationic, zwitteronic, and anionic species of cetirizine indicated intramolecular interactions via folded conformations, which render the molecule markedly more lipophilic than expected at physiological pH. Folded conformations were also found to predominate in monocationic and neutral hydroxyzine. The ionic partition diagram of cetirizine indicates that it acts as a proton transporter across interfaces under certain conditions of pH and Galvani potential difference. This study underlines the importance of conformational effects on the partition properties of cetirizine and hydroxyzine, as well as the complexity of its interfacial mechanisms of transfer. In particular, cetirizine can facilitateproton transfer, a property of potential biological relevance.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/04/20 alle ore 23:11:37