Crystallization of toxic glycol solvates of rifampin from glycerin and propylene glycol contaminated with ethylene glycol or diethylene glycol

Molecular Pharmaceutics

Volumn 8, Issue 3, 2011, Pages 877-888

  De Villiers, Melgardt M ^a   Caira, Mino R ^b   Li, Jinjing ^b   Strydom, Schalk J ^a,c   Bourne, Susan A ^b   Liebenberg, Wilna ^c  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

^c NORTH WEST UNIVERSITY   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

DIETHYLENE GLYCOL; ETHYLENE GLYCOL; GLYCEROL; PROPYLENE GLYCOL; RIFAMPICIN;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG CONTAMINATION; DRUG SOLUBILITY; DRUG STRUCTURE; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; RAMAN SPECTROMETRY;

CRYSTALLIZATION; ETHYLENE GLYCOL; ETHYLENE GLYCOLS; GLYCEROL; GLYCOLS; PROPYLENE GLYCOL; RIFAMPIN; SOLVENTS;

EID: 79958277101     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100459y     Document Type: Article

References (40)

1. Davidson, G. Rhodococcus Equi Pneumonia in Foals Int. J. Pharm. Compd. 2001, 5 (1) 55-57
2. Hillidge, C. J. Use of erythromycin-rifampin combination in treatment of Rhodococcus equi pneumonia Vet. Microbiol. 1987, 14 (3) 337-342 (Pubitemid 18016066)
3. Sweeney, C. R.; Sweeney, R. W.; Divers, T. J. Rhodococcus equi pneumonia in 48 foals: response to antimicrobial therapy Vet. Microbiol. 1987, 14 (3) 329-336 (Pubitemid 18016065)
4. Giguere, S; Prescott, J. F. Clinical manifestations, diagnosis, treatment, and prevention of Rhodococcus equi infections in foals Vet. Microbiol. 1997, 56 (3-4) 313-334 (Pubitemid 27339160)
5. The United States pharmacopeia. The national formulary. USP 30th revision (May 1, 2007). NF 25 th ed. (May 1, 2007). The United States Pharmacopeial Convention, Inc.: Rockville, MD; 2006.
6. Pelizza, G.; Nebuloni, M.; Ferrari, P.; Gallo, G. G. Polymorphism of rifampicin Il Farmaco 1977, 32, 471-481 (Pubitemid 8158645)
7. Gallo, G. G.; Radaelli, P. Rifampin. In Analytical profiles of drug substances; Florey, K., Ed.; Vol. 5, Academic Press: New York, 1976, pp 467 - 513.
8. Henwood, S. Q.; De Villiers, M. M.; Liebenberg, W.; Lötter, A. P. Solubility and dissolution properties of generic rifampicin raw materials Drug Dev. Ind. Pharm. 2000, 26, 403-408 (Pubitemid 30207711)
9. Henwood, S. Q.; Liebenberg, W.; Tiedt, L. R.; Lotter, A. P.; De Villiers, M. M. Characterization of the solubility and dissolution properties of several new rifampicin polymorphs, solvates, and hydrates Drug Dev. Ind. Pharm. 2001, 27, 1017-1030 (Pubitemid 34053197)
10. Agrawal, S.; Ashokraj, Y.; Bharatam, P. V.; Pillai, O.; Panchagnula, R. Solid state characterization of rifampicin samples and its biopharmaceutic relevance Eur. J. Pharm. Sci. 2004, 22, 127-144 (Pubitemid 38668679)
11. Leth, P. M.; Gregersen, M. Ethylene glycol poisoning Forensic Sci Int. 2005, 155, 179-184 (Pubitemid 41454955)
12. Barr, D. B.; Barr, J. R.; Weerasekera, G.; Wamsley, J.; Kalb, S. R.; Sjodin, A.; Schier, J. G.; Rentz, E. D.; Lewis, L.; Rubin, C.; Needham, L. L.; Jones, R. L.; Sampson, E. J. Identification and quantification of diethylene glycol in pharmaceuticals implicated in poisoning epidemics: an historical laboratory perspective J. Anal. Toxicol. 2007, 31 (6) 295-303 (Pubitemid 47292720)
13. O'Brien, K. L.; Selanikio, J. D.; Hecdivert, C.; Placide, M. F.; Louis, M.; Barr, D. B.; Barr, J. R.; Hospedales, C. J.; Lewis, M. J.; Schwartz, B.; Philen, R. M.; St. Victor, S.; Espindola, J.; Needham, L. L.; Denerville, K. Epidemic of pediatric deaths from acute renal failure caused by diethylene glycol poisoning. Acute Renal Failure Investigation Team JAMA, J. Am. Med. Assoc. 1998, 279 (15) 1175-1180 (Pubitemid 28193427)
14. Geiling, E. M. K.; Cannon, P. R. Pathologic effects of elixir of sulfanilamide (diethylene glycol) poisoning JAMA, J. Am. Med. Assoc. 1938, 111, 919-926
15. Calvery, H. O.; Klumpp, T. G. The toxicity for human beings of diethylene glycol with sulfanilamide South Med. J. 1939, 32, 1105-1109
16. Wax, P. M. Elixirs, diluents, and the passage of the 1938 Federal Food, Drug and Cosmetic Act Ann. Intern. Med. 1995, 122, 456-461
17. Bowie, M. D.; McKenzie, D. Diethylene glycol poisoning in children S. Afr. Med. J. 1972, 46, 931-934
18. Pandya, S. K. An unmitigated tragedy BMJ 1988, 297, 117-119
19. Okuonghae, H. O.; Ighogboja, I. S.; Lawson, J. O. Nwana EJC. Diethylene glycol poisoning in Nigerian children Ann. Trop. Pediatr. 1992, 12, 235-238
20. Hanif, M.; Mobarak, M. R.; Ronan, A.; Rahman, D.; Donovan, J. J.; Bennish, M. L. Fatal renal failure caused by diethylene glycol in paracetamol elixir: the Bangladesh epidemic BMJ 1995, 311, 88-91
21. Luis, A.; Ferrari, L. G. Clinical parameters, postmortem analysis and estimation of lethal dose in victims of a massive intoxication with diethylene glycol Forensic Sci. Int. 2005, 153, 45-51
22. Rentz, E. D.; Lewis, L.; Mujica, O. J.; Barr, D. B.; Schier, J. G.; Weerasekera, G.; Kuklenyik, P.; McGeehin, M.; Osterloh, J.; Wamsley, J.; Lum, W.; Alleyne, C.; Sosa, N.; Motta, J.; Rubin, C. Outbreak of acute renal failure in Panama in 2006: a case-control study Bull. W.H.O. 2008, 86 (10) 749-756
23. Nigeria: NAFDAC Arraigns My Pikin Producers. FDAnews Drug Daily Bull. 2009; 6 (46) (http://www.fdanews.com/newsletter/article?articleId= 115155&issueId=12459).
24. Elkheshen, S. A.; Badawi, S. S.; Badawi, A. A. Optimization of a reconstitutable suspension of rifampicin using 24 factorial design Drug Dev. Ind. Pharm. 1996, 22 (7) 623-630 (Pubitemid 26245747)
25. Nahata, M. C.; Morosco, R. S.; Hipple, T. F. Stability of rifampin in two suspensions at room temperature J. Clin. Pharm. Ther. 1994, 19 (4) 263-265 (Pubitemid 24257464)
26. Nahata, M. C.; Morosco, R. S.; Hipple, T. F. Effect of preparation method and storage on rifampin concentration in suspensions Ann Pharmacother. 1994, 28 (2) 182-185 (Pubitemid 24073453)
27. Krukenberg, C. C.; Mischler, P. G.; Massad, E. N.; Moore, L. A.; Chandler, A. D. Stability of 1% rifampin suspensions prepared in five syrups Am. J. Hosp. Pharm. 1986, 43 (9) 2225-2228 (Pubitemid 16015099)
28. Sheldrick, G. M. SHELXH Acta Crystallogr., Sect. A 2008, 64, 112-122
29. Lötter, A. P.; Flanagan, D. R.; Palepu, N. R.; Guillory, J. K. A simple reproducible method for determining dissolution rates of hydrophobic powders Pharm Technol. 1983, 7, 55-66
30. Moore, J. W.; Flanner, H. H. Mathematical Comparison of curves with an emphasis on in vitro dissolution profiles Pharm. Technol. 1996, 20 (6) 64-74 (Pubitemid 126450495)
31. 2O Acta Crystallogr., Sect. B 1975, 31, 1454-1462
32. Rubino, J. T.; Yalkowsky, S. H. Cosolvency and cosolvent polarity Pharm. Res. 1987, 4 (3) 220-230 (Pubitemid 17110396)
33. Yalkowsky, S. H.; Flynn, G. L.; Amidon, G. L. Solubility of nonelectrolytes in polar solvents J. Pharm. Sci. 1972, 61 (6) 983-984
34. Yalkowsky, S. H.; Rubino, J. T. Solubilization of cosolvents. I: Organic solutes in propylene glycol-water mixtures J. Pharm. Sci. 1985, 74 (4) 416-421 (Pubitemid 15112932)
35. Millard, J. W.; Alvarez-Nunez, F. A.; Yalkowsky, S. H. Solubilization by cosolvents establishing useful constants for the log-linear model Int. J. Pharm. 2002, 245 (1-2) 153-166 (Pubitemid 35299901)
36. Rubino, J. T.; Yalkowsky, S. H. Cosolvency and deviations from log-linear solubilization Pharm. Res. 1987, 4 (3) 231-236 (Pubitemid 17110397)
37. Bogardus, J. B. Crystalline anhydrous-hydrate phase changes of caffeine and theophylline in solvent-water mixtures J. Pharm. Sci. 1983, 72 (7) 837-838 (Pubitemid 13076426)
38. Damian, F.; Blaton, N.; Naesens, L.; Balzarini, J.; Kinget, R.; Augustijns, P.; Van den Mooter, G. Physicochemical characterization of solid dispersions of the antiviral agent UC-781 with polyethylene glycol 6000 and Gelucire 44/14 Eur. J. Pharmacol. 2000, 10 (4) 311-322 (Pubitemid 30317467)
39. Lewis, R. A. Lewis' Dictionary of Toxicology; Lewis Publishers: Boca Raton; 1998.
40. Gryniewicz, C. M.; Spencer, J. A.; Hankins, M.; Kauffman, J. F. Spectroscopic methods for rapid determination of diethylene glycol in glycerin Am. Pharm. Rev. 2007, 10 (7) 24-30