Biopharmaceutic Profiling of Salts to Improve Absorption of Poorly Soluble Basic Drugs

J Pharm Sci. 2016 Nov;105(11):3314-3323. doi: 10.1016/j.xphs.2016.07.016. Epub 2016 Sep 13.

Abstract

AZD1175 and AZD2207 are 2 highly lipophilic compounds with a significant risk of not achieving therapeutic plasma concentrations due to solubility-limited absorption. The compounds have the same molecular weight and minimal structural differences. The aim of the present work was to investigate whether salts could be applied to improve the intestinal absorption, and the subsequent in vivo exposure. Drug solubilities, dissolution rates, and degree of supersaturation and precipitation were determined in biorelevant media. Dog studies were performed, in the absence and presence of a precipitation inhibitor (hydroxypropyl methylcellulose). Finally, a human phase I study was performed. For AZD1175, there was a good agreement between dissolution rates, in vivo exposure in dog, and the obtained exposure in human with the selected hemi-1,5-naphthalenedisulfonate of the compound. For AZD2207, the picture was more complex. The same counter ion was selected for the study in man. In addition, the chloride salt of AZD2207 showed promising data in the presence of a precipitation inhibitor in vitro and in dog that, however, could not be repeated in man. The differences in observations between the 2 compounds could be attributed to the difference in solubility and to the degree of supersaturation in the gastric environment rather than in the intestine.

Keywords: bioavailability; dissolution; intestinal absorption; pharmacokinetics; precipitation; salts; solubility-limited absorption; supersaturation.

Publication types

  • Randomized Controlled Trial

MeSH terms

  • Administration, Oral
  • Animals
  • Biopharmaceutics / methods*
  • Cannabinoid Receptor Antagonists / administration & dosage
  • Cannabinoid Receptor Antagonists / chemistry*
  • Cannabinoid Receptor Antagonists / metabolism*
  • Cross-Over Studies
  • Dogs
  • Dose-Response Relationship, Drug
  • Female
  • Humans
  • Hydrogen-Ion Concentration
  • Intestinal Absorption / drug effects
  • Intestinal Absorption / physiology
  • Male
  • Salts / administration & dosage
  • Salts / chemistry*
  • Salts / metabolism*
  • Solubility

Substances

  • Cannabinoid Receptor Antagonists
  • Salts