Characterization of four crystal polymorphs and a monohydrate of s-bupivacaine hydrochloride (levobupivacaine hydrochloride)

Journal of Pharmaceutical Sciences
V NiederwangerUlrich J Griesser

Abstract

Five crystal forms of the amide-type local anesthetic S-bupivacaine hydrochloride (levobupivacaine) were prepared and characterized by means of thermal analytical methods, FTIR- and Raman-spectroscopy, powder X-ray diffractometry, and moisture sorption analysis. Commercial lots of the substance may consist of form A degrees , the thermodynamically stable form at 20 degrees C, and/or the metastable form C. Form A degrees shows a highly reversible transformation into form B (T(trs): 85.3 degrees C) with a transition enthalpy of 4.6 kJ mol(-1). The hysteresis between the experimental transition temperatures is 3.5 K, indicating a very weak kinetic control. The hydrate shows a variable water content (0.71-1.14 mol/mol) between 10% and 90% relative humidity (RH) and dehydrates to form C under dry conditions or at elevated temperatures. All anhydrous forms transform to the hydrate at and above 90% RH (25 degrees C). Form C slowly converts to form A degrees on storage and is the polymorph with the highest hygroscopicity. At higher temperatures all forms transform into form D, which is kinetically stable at 20 degrees C. It is concluded that the forms A degrees , B, and D are enantiotropically related, whereas form C shows a monotropic...Continue Reading

References

Dec 22, 1999·Angewandte Chemie·J BernsteinJ O Henck
Jan 3, 2007·Physical Chemistry Chemical Physics : PCCP·Robin K HarrisUlrich J Griesser

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Citations

Apr 13, 2011·Analytical Chemistry·R K Gilpin, C S Gilpin
Aug 21, 2010·Journal of Synchrotron Radiation·Anna BergamaschiXintian Shi
Jan 20, 2011·Journal of Pharmaceutical Sciences·Giovanna BruniAmedeo Marini
Apr 1, 2011·Journal of Pharmaceutical Sciences·Harry G Brittain
Dec 17, 2009·Journal of Pharmaceutical and Biomedical Analysis·Mario JugPaola Mura
Apr 4, 2017·International Journal of Pharmaceutics·Murillo L MartinsHeloisa N Bordallo
Feb 12, 2020·International Journal of Molecular Sciences·Jian-Ming ChenShih-Jung Liu
Mar 17, 2019·Canadian Journal of Anaesthesia = Journal Canadien D'anesthésie·Ellen K WasanJonathan Gamble
Nov 9, 2020·Journal of Pharmaceutical Sciences·Kailin XuSuqing Zhao

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