Bioreversible quaternary N-acyloxymethyl derivatives of the tertiary amines bupivacaine and lidocaine--synthesis, aqueous solubility and stability in buffer, human plasma and simulated intestinal fluid.

[1]  S. G. Kuznetsov,et al.  Quaternary ammonium salts with labile N+-C bonds as drug precursors , 1980, Pharmaceutical Chemistry Journal.

[2]  T. Liljefors,et al.  Assessment of the combined approach of N-alkylation and salt formation to enhance aqueous solubility of tertiary amines using bupivacaine as a model drug. , 2005, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[3]  G. Amidon,et al.  Gastrointestinal Dissolution and Absorption of Drugs , 2004 .

[4]  S. Larsen,et al.  Kinetics of degradation of 4-imidazolidinone prodrug types obtained from reacting prilocaine with formaldehyde and acetaldehyde. , 2003, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[5]  Han van de Waterbeemd,et al.  Drug bioavailability : estimation of solubility, permeability, absorption and bioavailability , 2003 .

[6]  T. Heimbach.  Oral phosphate prodrugs: Absorption rate limit considerations. , 2003 .

[7]  C. Larsen,et al.  Characteristics of drug substances in oily solutions. Drug release rate, partitioning and solubility. , 2002, International journal of pharmaceutics.

[8]  S. Sampson,et al.  Prodrugs of butyric acid. Novel derivatives possessing increased aqueous solubility and potential for treating cancer and blood diseases. , 2001, European journal of medicinal chemistry.

[9]  V. Stella,et al.  A novel prodrug approach for tertiary amines. 3. In vivo evaluation of two N-phosphonooxymethyl prodrugs in rats and dogs. , 1999, Journal of pharmaceutical sciences.

[10]  V. Stella,et al.  A novel prodrug approach for tertiary amines. 2. Physicochemical and in vitro enzymatic evaluation of selected N-phosphonooxymethyl prodrugs. , 1999, Journal of pharmaceutical sciences.

[11]  V. Stella,et al.  Novel prodrug approach for tertiary amines: synthesis and preliminary evaluation of N-phosphonooxymethyl prodrugs. , 1999, Journal of medicinal chemistry.

[12]  K. Sloan,et al.  1-Alkylcarbonyloxymethyl prodrugs of 5-fluorouracil (5-FU): synthesis, physicochemical properties, and topical delivery of 5-FU. , 1998, Journal of pharmaceutical sciences.

[13]  S. Davidsen,et al.  N-(acyloxyalkyl)pyridinium salts as soluble prodrugs of a potent platelet activating factor antagonist. , 1994, Journal of medicinal chemistry.

[14]  M. Maniar,et al.  pH-Dependent solubility and dissolution of bupivacaine and its relevance to the formulation of a controlled release system , 1993 .

[15]  E. Falch,et al.  Prodrugs of thiabendazole with increased water-solubility. , 1992, Acta pharmaceutica Nordica.

[16]  K. A. Connors.  Chemical Kinetics: The Study of Reaction Rates in Solution , 1990 .

[17]  K. Sloan,et al.  Effects of vehicles and prodrug properties and their interactions on the delivery of 6-mercaptopurine through skin: S6-acyloxymethyl-6-mercaptopurine prodrugs. , 1987, Journal of pharmaceutical sciences.

[18]  James I. Wells,et al.  Pharmaceutical preformulation : the physicochemical properties of drug substances , 1988 .

[19]  E. Falch,et al.  Prodrugs of 5-fluorouracil. IV. Hydrolysis kinetics, bioactivation and physicochemical properties of various N-acyloxymethyl derivatives of 5-fluorouracil , 1985 .

[20]  Hans Bundgaard,et al.  Design of prodrugs , 1985 .

[21]  B. Møllgaard,et al.  Pro-drugs as drug delivery systems XXIII. Improved dermal delivery of 5-fluorouracil through human skin via N-acyloxymethyl pro-drug derivatives , 1982 .

[22]  R Woods,et al.  Soft drugs. 3. A new class of anticholinergic agents. , 1980, Journal of medicinal chemistry.

[23]  N. Nakano.  Temperature-dependent aqueous solubilities of lidocaine, mepivacaine, and bupivacaine. , 1979, Journal of pharmaceutical sciences.

[24]  Y. Gotoh,et al.  3-Hydroxy-2-naphthoates of Lidocaine, Mepivacaine, and Bupivacaine and Their Dissolution Characteristics , 1978 .

[25]  G. Åberg,et al.  Some physiochemical properties of the racemates and the optically active isomers of two local anaesthetic compounds. , 1971, Acta pharmaceutica Suecica.

[26]  N. Leonard,et al.  Synthesis of 3-(2'-deoxy-D-erythro-pentofuranosyl)adenine. Application of a new protecting group, pivaloyloxymethyl(Pom) , 1967 .