Optimizing solubility and permeability of a biopharmaceutics classification system (BCS) class 4 antibiotic drug using lipophilic fragments disturbing the crystal lattice.
J Med Chem
; 56(6): 2690-4, 2013 Mar 28.
Article
em En
| MEDLINE
| ID: mdl-23432334
ABSTRACT
Esterification was used to simultaneously increase solubility and permeability of ciprofloxacin, a biopharmaceutics classification system (BCS) class 4 drug (low solubility/low permeability) with solid-state limited solubility. Molecular flexibility was increased to disturb the crystal lattice, lower the melting point, and thereby improve the solubility, whereas lipophilicity was increased to enhance the intestinal permeability. These structural changes resulted in BCS class 1 analogues (high solubility/high permeability) emphasizing that simple medicinal chemistry may improve both these properties.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Descoberta de Drogas
/
Interações Hidrofóbicas e Hidrofílicas
/
Antibacterianos
Limite:
Humans
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article