Preactivated thiomers: evaluation of gastroretentive minitablets

Int J Pharm. 2013 Nov 18;456(2):473-9. doi: 10.1016/j.ijpharm.2013.08.032. Epub 2013 Aug 30.

Abstract

The object of this study was to evaluate the potential of a recently developed preactivated thiolated pectin derivative as mucoadhesive excipient in drug delivery to the gastric cavity. Pectin (Pec) was chemically modified with L-cysteine (Cys). The free thiol groups of resulting thiomer were activated with 2-mercaptonicotinic acid (MNA) in order to improve stability and reactivity of attached thiol groups over a broad pH range. Multiunit dosage form properties of the resulting conjugate (Pec-Cys-MNA) were compared to unmodified pectin and the intermediate thiolated using rosuvastatin calcium as a model drug in loaded minitablets. Obtained results were compared with unmodified pectin and the intermediate thiolated pectin. Approximately half of attached thiol groups (507 μmol/g polymer) have been preactivated. Minitablets were evaluated regarding mucoadhesive properties, hardness, disintegration behavior, swelling characteristics and release of rosuvastatin calcium. Mediated by covalent bonds between the polymer and cysteine-rich subdomains in mucus, total work of adhesion increased more than 5-fold. The modification had no impact on hardness of compressed tablets but implementation of the aromatic ligand went along with reduction in hydrophilic properties. Disintegration time was prolonged more than 2-fold while water uptake capacity increased. Weight gain for Pec-Cys-MNA was at least 16-fold. Further, a sustained release of rosuvastatin calcium over 36 h was determined. Neither biodegradability nor CaCo-2 cell viability was affected. The study shows that Pec-Cys-MNA is a promising excipient for the development of mucoadhesive gastric dosage form.

Keywords: 2-Mercaptonicotinic acid (CID 673681); Gastric; Mucoadhesive drug delivery system; Pectin (CID 441476); Preactivated thiomers; Rosuvastatin; Swellable polymer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Caco-2 Cells
  • Cell Survival / drug effects
  • Cell Survival / physiology
  • Cysteine / chemistry*
  • Cysteine / pharmacology
  • Delayed-Action Preparations / chemistry
  • Delayed-Action Preparations / pharmacology
  • Drug Evaluation, Preclinical / methods
  • Gastric Mucosa / drug effects*
  • Gastric Mucosa / metabolism
  • Gastrointestinal Agents / chemistry*
  • Gastrointestinal Agents / pharmacology
  • Humans
  • Nicotinic Acids / chemistry*
  • Nicotinic Acids / pharmacology
  • Pectins / chemistry*
  • Pectins / pharmacology
  • Sulfhydryl Compounds / chemistry*
  • Sulfhydryl Compounds / pharmacology
  • Swine
  • Tablets

Substances

  • Delayed-Action Preparations
  • Gastrointestinal Agents
  • Nicotinic Acids
  • Sulfhydryl Compounds
  • Tablets
  • Pectins
  • 2-mercaptonicotinic acid
  • Cysteine