Comparative effects of some hydrophilic excipients on the rate of gabapentin and baclofen lactamization in lyophilized formulations

Int J Pharm. 2007 Mar 6;332(1-2):98-106. doi: 10.1016/j.ijpharm.2006.09.053. Epub 2006 Oct 5.

Abstract

The aim of this study was to gain insights into the role played by some excipients on the stability of gabapentin 1 and baclofen 2 which can undergo degradation giving rise to the corresponding lactams 2-azaspiro[4.5]decan-3-one 3 and 4-(4-chlorophenyl)-2-pyrrolidone 4, respectively. A screening study was carried out on drug and drug-excipient freeze-dried mixtures at 50 degrees C and under three different humidity values by using a number of commonly available excipients. These include hydroxypropyl-beta-(HP-beta-CD), sulfobutyl-beta-cyclodextrin (SBE-beta-CD), lactose, raffinose, trehalose, PVP-K30 and mannitol. For most cases, it was found that the lactam formation can be satisfactory described by an apparent zero-order equation. Excipients shown to negatively impact gabapentin stability are HP-beta-CD, SBE-beta-CD, lactose and PVP K30 while only this last excipient had a significant effect on the degradation of baclofen. The results can be rationalized in terms of conformational factors favouring the intramolecular dehydration reaction. A positive effect of moisture on the lactamization process was observed under some circumstances. Water may provide a favourable environment for degradation. These findings, taken together, should be considered during the selection of excipients for a possible formulation of gabapentin and baclofen.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Anticonvulsants / chemistry*
  • Baclofen / chemistry*
  • Calorimetry, Differential Scanning
  • Chemistry, Pharmaceutical
  • Cyclohexanecarboxylic Acids / chemistry*
  • Drug Stability
  • Excipients / chemistry*
  • Freeze Drying
  • Gabapentin
  • Humidity
  • Kinetics
  • Lactams / chemistry*
  • Lactose / chemistry
  • Mannitol / chemistry
  • Models, Chemical
  • Molecular Structure
  • Parasympatholytics / chemistry*
  • Povidone / chemistry
  • Raffinose / chemistry
  • Technology, Pharmaceutical / methods
  • Temperature
  • Thermogravimetry
  • Trehalose / chemistry
  • Water / chemistry
  • beta-Cyclodextrins / chemistry
  • gamma-Aminobutyric Acid / chemistry*

Substances

  • Amines
  • Anticonvulsants
  • Cyclohexanecarboxylic Acids
  • Excipients
  • Lactams
  • Parasympatholytics
  • beta-Cyclodextrins
  • Water
  • Mannitol
  • gamma-Aminobutyric Acid
  • Gabapentin
  • Trehalose
  • Povidone
  • Baclofen
  • Lactose
  • Raffinose