Physical characterization of pentamidine isethionate during freeze-drying-relevance to development of stable lyophilized product

Journal of Pharmaceutical Sciences

Volumn 101, Issue 5, 2012, Pages 1732-1743

  Sundaramurthi, Prakash ^a,b   Burcusa, Michael R ^a   Suryanarayanan, Raj ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b Pharmaceutical R and D   (United States)

Author keywords

Amorphous; Crystallization; Dehydration; Differential scanning calorimetry; Formulation; Freeze drying; Pentamidine isethionate; Physical characterization; Physical stability; Polymorphism; X ray diffractometry

Indexed keywords

CHEMICAL COMPOUND; PENTAMIDINE ISETHIONATE; SOLVENT; TRIHYDRATE; UNCLASSIFIED DRUG; PENTAMIDINE;

AQUEOUS SOLUTION; ARTICLE; CONCENTRATION PROCESS; COOLING; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; FREEZE DRYING; MOLECULAR STABILITY; PHYSICAL CHEMISTRY; SOLUTE; X RAY DIFFRACTION; CHEMISTRY;

CALORIMETRY, DIFFERENTIAL SCANNING; FREEZE DRYING; PENTAMIDINE; X-RAY DIFFRACTION;

EID: 84864306186     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23055     Document Type: Article

References (40)

1. Byrn SR, Pfeiffer RR, Stowell JG. 1999. Solid-state chemistry of drugs. West Lafayatte, Indiana: SSCI.
2. Panchagnula R, Sundaramurthy P, Pillai O, Agrawal S, Raj YA. 2004. Solid-state characterization of mefenamic acid. J Pharm Sci 93(4):1019-1029.
3. Hilfiker R, Blatter F, von Raumer M. 2006. Relevance of solid-state properties for pharmaceutical solids. In Polymorphism: In the pharmaceutical industry; Hilfiker R, Ed. Weinheim, Germany: Wiley-VCH, pp 1-20.
4. Oberholtzer ER, Brenner GS. 1979. Cefoxitin sodium: Solution and solid-state chemical stability studies. J Pharm Sci 68(7):863-866.
5. Milton N, Nail SL. 1996. The physical state of nafcillin sodium in frozen aqueous solutions and freeze-dried powders. Pharm Dev Technol 3:269-277.
6. Koyama Y, Kamat M, Angelis RJD, Srinivasan R, DeLuca PP. 1988. Effect of solvent addition and thermal treatment on freeze drying of cephazolin sodium. J Parenter Sci Technol 42:47-52.
7. Pikal MJ, Lukes AL, Lang JE. 1977. Thermal decomposition of amorphous β-lactam antibacterials. J Pharm Sci 66(9):1312-1316.
8. Huang LF, Tong WQ. 2004. Impact of solid state properties on developability assessment of drug candidates. Adv Drug Deliv Rev 56(3):321-334.
9. Datta S, Grant DJW. 2004. Crystal structures of drugs: Advances in determination, prediction and engineering. Nat Rev 3(1):42-57.
10. Chongprasert S, Griesser UJ, Bottorff AT, Williams NA, Byrn SR, Nail SL. 1998. Effects of freeze-dry processing conditions on the crystallization of pentamidine isethionate. J Pharm Sci 87(9):1155-1160.
11. Petit S, Coquerel G. 2006. The amorphous state. In Polymorphism: In the pharmaceutical industry; Hilfiker R, Ed. Weinheim, Germany: Wiley-VCH, pp 259-186.
12. Williams NA, Schwinke DL. 1994. Low temperature properties of lyophilized solutions and their influence on lyophilization cycle design: Pentamidine isethionate. J Pharm Sci Technol 48(3):135-139.
13. Steele G. 1990. An observation of polymorphism in pentamidine isethionate. J Pharm Pharmacol 42(2):121-122.
14. Paul M, Fessi H, Laatiris A, Boulard Y, Burand R, Deniau M, Astier A. 1997. Pentamidine-loaded poly(d, l-lactide) nanoparticles: Physicochemical properties and stability work. Int J Pharm 159:223-232.
15. Goa KL, Campoli-Richards DM. 1987. Pentamidine isethionate. A review of its antiprotozoal activity, pharmacokinetic properties and therapeutic use in Pneumocystis carinii pneumonia. Drugs 33(3):242-258.
16. Stelliou I, Venthoye G, Taylor KMG. 1993. Manipulating the temperature of pentamidine isethionate solutions in jet nebulizers. Int J Pharm 99(1):R1-R3.
17. Conte JE Jr, Chernoff D, Feigal DW Jr, Joseph P, McDonald C, Golden JA. 1990. Intravenous or inhaled pentamidine for treating Pneumocystis carinii pneumonia in AIDS. A randomized trial. Ann Intern Med 113(3):203-209.
18. NebuPent®. 2008. Package insert. Schaumburg, Illinois: AAP Pharmaceuticals, LLC.
19. Pentam®. 2008. Package insert. Schaumburg, Illinois: AAP Pharmaceuticals, LLC.
20. Lowe PR, Sansom CE, Schwalbe CH, Stevens MFG. 1989. Crystal structure and molecular modeling of the antimicrobial drug pentamidine. J Chem Soc Chem Commun(16):1164-1165.
21. Srikrishnan T, De CN, Alam AS, Kapoor J. 2004. Crystal and molecular structure of pentamidine diisthionate: An anti-protozoal drug used in AIDS related pneumonia. J Chem Crystallogr 34(11):813-818.
22. Burger A, Ramberger R. 1979. On the polymorphism of pharmaceuticals and other molecular crystals. I Theory of thermodynamic rules. Microchim Acta 72 (3-4):259-271
23. Grant DJW. 1999. Theory and origin of polymorphism. In Polymorphism in pharmaceutical solids; Brittain HG, Ed. New York: Marcel Dekker, pp 1-35.
24. Pyne A, Chatterjee K, Suryanarayanan R. 2003. Crystalline to amorphous transition of disodium hydrogen phosphate during primary drying. Pharm Res 20(5):802-803.
25. Varshney DB, Sundaramurthi P, Kumar S, Shalaev EY, Kang SW, Gatlin LA, Suryanarayanan R. 2009. Phase transitions in frozen systems and during freeze-drying: Quantification using synchrotron X-ray diffractometry. Pharm Res 26(7):1596-1606.
26. Chatterjee K, Shalaev EY, Suryanarayanan R. 2005. Raffinose crystallization during freeze-drying and its impact on recovery of protein activity. Pharm Res 22(2):303-309.
27. Sundaramurthi P, Shalaev E, Suryanarayanan R. 2010. "pH swing" in frozen solutions-Consequence of sequential crystallization of buffer components. J Phys Chem Lett 1(1):265-268.
28. Sundaramurthi P, Shalaev E, Suryanarayanan R. 2010. Calorimetric and diffractometric evidence for the sequential crystallization of buffer components and consequential pH swing in frozen solutions. J Phys Chem B 114:4915-4923.
29. Sundaramurthi P, Suryanarayanan R. 2011. The effect of crystallizing and non-crystallizing cosolutes on succinate buffer crystallization and the consequent pH shift in frozen solutions. Pharm Res 28(2):374-385.
30. Sundaramurthi P, Patapoff TW, Suryanarayanan R. 2010. Crystallization of trehalose in the frozen solutions and its phase behavior during drying. Pharm Res 27(11):2374-2383.
31. Korey DJ, Schwartz JB. 1989. Effects of excipients on the crystallization of pharmaceutical compounds during lyophilization. J Parenter Sci Technol 43:80-83.
32. Pyne A, Suryanarayanan R. 2003. The effect of additives on the crystallization of cefazolin sodium during freeze-drying. Pharm Res 20(2):283-291.
33. Connolly M, Debenedetti PG, Tung HH. 1996. Freeze crystallization of imipenem. J Pharm Sci 85(2):174-177.
34. Gelone S, Gennaro AR. 2005. Pharmaceutical and medicinal agents: Anti-infectives. In Remington: The science and practice of pharmacy; Troy DB, Ed. 21st ed. Philadelphia, Pennsylvania: Lippincott Williams & Wilkins, pp 1648.
35. Aladko LS, Manakov AY, Ogienko AG, Ancharov AI. 2009. New data on phase diagram and clathrate formation in the system water-isopropyl alcohol. J Incl Phenom Macrocycl Chem 63(1-2):151-157.
36. Kasraian K, DeLuca PP. 1995. Thermal analysis of the tertiary butyl alcohol-water system and its implications on freeze-drying. Pharm Res 12(4):484-490.
37. Gelone S, Gennaro AR. 2005. Pharmaceutical and medicinal agents: Anti-infectives. In Remington: The science and practice of pharmacy; Troy DB, Ed. 21st ed.Philadelphia, Pennsylvania: Lippincott Williams & Wilkins, pp 1669-1670.
38. Govindarajan R, Suryanarayan R. 2006. Processing-induced phase transformation and their implications on pharmaceutical product quality. In Polymorphism: In the pharmaceutical industry; Hilfiker R, Ed. Weinheim, Germany: Wiley-VCH, pp 333-364.
39. Sundaramurthi P, Suryanarayanan R. Calorimetric and complementary techniques to characterize frozen and freeze-dried systems. Adv Drug Deliv Rev(2011) doi:10.1016/j.addr.2011.12.004.
40. Varshney DB, Kumar S, Shalaev EY, Sundaramurthi P, Kang SW, Gatlin LA, Suryanarayanan R. 2007. Glycine crystallization in frozen and freeze-dried systems: Effect of pH and buffer concentration. Pharm Res 24(3):593-604.