Frontiers of Chemical Science and Engineering >
Polymorphism and crystal transformation of penicillin sulfoxide
Received date: 10 Sep 2011
Accepted date: 15 Oct 2011
Published date: 05 Dec 2011
Copyright
Penicillin sulfoxide is the intermediate for the synthesis of 7-amino-3-desacetoxycephalosporanic acid which is one of the most important nucleuses of cephalosporin antibiotic. In this contribution, two crystal structures of penicillin sulfoxide (forms I and II) were determined by X-ray diffraction, and their thermotropic properties were investigated by differential scanning calorimetry (DSC). Furthermore, the transformation of form II to form I was studied quantitatively by Raman spectroscopy, and its rates at different temperatures were determined. The results indicate that penicillin sulfoxide is more stable as form I, and the temperature plays an important role in the crystal transformation.
Dingding JING , Yongli WANG , Zhijian CHEN , Lina ZHOU , Jingkang WANG . Polymorphism and crystal transformation of penicillin sulfoxide[J]. Frontiers of Chemical Science and Engineering, 2011 , 5(4) : 442 -447 . DOI: 10.1007/s11705-011-1140-x
| 1 |
Haleblian J, McCrone W. Pharmaceutical applications of polymorphism. Journal of Pharmaceutical Sciences, 1969, 58(8): 911–929
|
| 2 |
Haleblian J K. Characterization of habits and crystalline modification of solids and their pharmaceutical applications. Journal of Pharmaceutical Sciences, 1975, 64(8): 1269–1288
|
| 3 |
Threlfall T L. Analyst of organic polymorphs: a review. Analyst, 1995, 120(10): 2435–2460
|
| 4 |
Wu H, Ge X, Yu H, Chen L. Comparisons of crystal form of raphides to toxicity raphides in four poisonous herbs of Araceae family. China Journal of Chinese Materia Medica, 2010, 35(9): 1152–1155 (in Chinese)
|
| 5 |
Brittain H G. In Polymorphism in Pharmaceutical Solids. New York: Marcel Dekker Inc, 1999, 95: 1–3
|
| 6 |
Fu T, Guo Y. The study of the synthesized technology of 7-amino-3-decase toxycephalosporanic acid. Hebei Chemical Engineering and Industry, 2009, 32: 19–21 (in Chinese)
|
| 7 |
Robert A A, Donglas O S. Penicillin sulfoxide conversion process. US patent, <patent>3592751</patent>, 1971, 2–4
|
| 8 |
Patrick J B. Penicillin oxidation process. <patent>US patent, 3904605</patent>, 1975, 6
|
| 9 |
Ono T, ter Horst J H, Jansens P J. Quantitative measurement of the polymorphic transformation of L-glutamic acid using in-situ Raman spectroscopy. Crystal Growth & Design, 2004, 4(3): 465–469
|
| 10 |
Stephenson G A, Forbes R A, Reutzel-Edens S M. Characterization of the solid state: quantitative issues. Advanced Drug Delivery Reviews, 2001, 48(1): 67–90
|
| 11 |
Giron D.Thermal analysis, microcalorimetry and combined techniques for the study of pharmaceuticals. Journal of Thermal Analysis and Calorimetry, 1999, 56(3): 1285–1304
|
| 12 |
Wang J. The new technology of the preparation of 7-ADCA. Dissertation for the Master Degree. Tianjin: Tianjin University, 2003, 1 (in Chinese)
|
| 13 |
Kitamura M. Controlling factor of polymorphism in crystallization process. Journal of Crystal Growth, 2002, 237-239: 2205–2214
|
| 14 |
O’Brien L E, Timmins P, Williams A C, York P. Use of in situ FT-Raman spectroscopy to study the kinetics of the transformation of carbamazepine polymorphs. Journal of Pharmaceutical and Biomedical Analysis, 2004, 36(2): 335–340
|
| 15 |
Duan E H, Zhao D S, Wang J, Li M L. 1-Oxo-6-(2-phenylacetylamino)-1-penicillanic acid. Acta Crystallographica. Section E, Structure Reports Online, 2006, 62(8): o3249–o3250
|
| 16 |
Wang F, Wachter J A, Antosz F J, Berglund K A. An Investigation of solvent-mediated polymorphic transformation of progesterone using in situ Raman spectroscopy. Organic Process Research & Development , 2000, 4(5): 391–395
|
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