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Crystal pseudopolymorphism of secnidazole bulk drug, C7H11N3O3

Published online by Cambridge University Press:  10 January 2013

Héctor Novoa de Armas ,
Rolando González Hernández ,
Anailien Boza Rivera ,
Ramón Pomés Hernández  and
Irminia Herrera Martínez
Héctor Novoa de Armas*
Affiliation:
Center of Pharmaceutical Chemistry, Analytical Department, P.O. Box 16042, Havana, Cuba
Rolando González Hernández
Affiliation:
Center of Pharmaceutical Chemistry, Analytical Department, P.O. Box 16042, Havana, Cuba
Anailien Boza Rivera
Affiliation:
Center of Pharmaceutical Chemistry, Analytical Department, P.O. Box 16042, Havana, Cuba
Ramón Pomés Hernández
Affiliation:
National Center for Scientific Research, P.O. Box 6990, Havana, Cuba
Irminia Herrera Martínez
Affiliation:
Central Forensic Laboratory, Zulueta E/e Muralla y Teniente Rey, Havana, Cuba
*
a)Author to whom correspondence should be addressed. Present address: Katholieke Universiteit Leuven (KUL). Faculteit Farmaceutische Wetenschappen. Laboratorium voor Analytische Chemie en Medicinale Fysicochemie. Van Evenstraat 4, 3000 Leuven, Belgium. E-mail: hector.novoa@farm.kuleuven.ac.be
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Abstract

An indexed powder diffraction pattern and related crystallographic data are reported for secnidazole [C7H11N3O3, IUPAC name: 1-(2-hydroxypropyl)-2-methyl-5-nitroimidazole], which is not represented in the Powder Diffraction File. The unit cell dimensions were determined from diffractometer methods, using monochromatic CuKα1 radiation, and evaluated by indexing programs. The monoclinic cell found for 1-(2-hydroxypropyl)-2-methyl-5-nitroimidazole is: a=12.426(2) Å, b=12.173(2) Å, c=6.656(1) Å, β=100.19(1)°, Z=4, space group P21/c (No. 14), Dx=1.271 g/cm3. Crystallization of an anhydrous powdered sample of secnidazole in a buffer solution of Na2B4O7 and NaOH (pH 10.4) resulted in crystals that contained water of crystallization, as shown by single crystal structure determination. Secnidazole exhibits crystal pseudopolymorphism, because the experimental powder pattern of the anhydrous form and the calculated pattern from the structure determination of the hydrate form are similar. Observed powder diffraction data for this drug were interpreted with the aid of a calculated pattern based upon the crystal structure determined. The cell found by TREOR90P for anhydrous secnidazole is in good agreement with that of the hemihydrate form determined from single crystal diffraction: a=12.424(2) Å, b=12.187(2) Å, c=6.662(1) Å, β=100.9(1)°; Z=4.

Keywords

X-ray powder diffractionsecnidazolepolymorphismindexingsingle crystal diffraction
Type
Research Article
Information
Powder Diffraction , Volume 14 , Issue 2 , June 1999 , pp. 136 - 141
Copyright
Copyright © Cambridge University Press 1999

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References

Boza, A., González, R., Novoa, H., Valdéz, M., and Cuéllar, D. (1998). “Physicochemical and solid state characterization of secnidazole,” Int. J. Pharm. (submitted).Google Scholar
Brama, R., Gramana, R., and Bavadhanulu, A. (1987). “Polymorphism in drugs and its significance in therapeutics,” J. Sci. Ind. Res. 46, 450–455.Google Scholar
Budavari, S., O’Neil, M. J., Heckelman, P. E., and Kinneary, J. F., editors (1996). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biological. 12th ed. (Merck, Whitehouse Station, NJ).Google Scholar
Byrn, R. S. (1982). Solid State Chemistry of Drugs (Academic, New York).Google Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern indexing,” J. Appl. Crystallogr. 1, 108–109.CrossRefGoogle Scholar
Lowe-Ma, C. K. (1991). “Powder diffraction data for two energetic materials and a proposed intensity figure of merit,” Powder Diffr. 6, 31–35.CrossRefGoogle Scholar
Martindale. The Extra Pharmacopoeia. (1996). 31th ed., edited by James E. F. Reynolds (The Pharmaceutical Press, London, UK).Google Scholar
McCarthy, G. J. (1989). “X-ray diffraction data for SnO 2. An illustration of the new powder data evaluation methods,” Powder Diffr. 4, 156–159.CrossRefGoogle Scholar
Mighell, A. D., Hubbard, C. R., and Stalick, J. K. (1981). “NBS*AIDS80: A Fortran Program for Crystallographic Data Evaluation,” Natl. Bur. Stand. Tech. (U.S.). Note No. 1141. (NBS*AIDS83 is an expanded version of NBS*AIDS80).CrossRefGoogle Scholar
Novoa de Armas, H., Dago Morales, A., González Hernández, R., Li, N., and Pomés Hernández, R. (1997). “Estructura cristalina del (hidroxi-2-propil)-1-metil-2-nitro-5-imidazol hemihidratado,” Rev. CENIC (Ciencias Químicas) 28, 89–92.Google Scholar
Pfeiffer, R. R., Yang, K. S., and Tucker, M. A. (1970). “Crystal pseudopolymorphism of cephaloglycin and cephalexin,” J. Pharm. Sci. 59, 1809–1814.CrossRefGoogle ScholarPubMed
Sakthivel, A., and Young, R. A. (1991). Program DBWS-9006PC for Rietveld Analysis of X-ray and Neutron Powder Diffraction Pattern (Georgia Institute of Technology, Atlanta, GA).Google Scholar
Sheldrick, G. M. (1991). SHELXTL-Plus. Release 4.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin.Google Scholar
Sheldrick, G. M. (1993). “Program for the Refinement of Crystal Structures,” University of Gottingen, Germany.Google Scholar
Siemens D5000/DIFFRAT-AT Version 3.2. (1993). Siemens analytical X-ray Instruments, Inc. Karlsruhe, Germany.Google Scholar
Smith, G. S., and Snyder, R. L. (1979). “F N: A criterion for rating powder diffraction patterns and evaluating the reliability of powder pattern indexing,” J. Appl. Crystallogr. 12, 60–65.CrossRefGoogle Scholar
Snyder, R. L. (1983). “Accuracy in angle and intensity measurements in X-ray powder diffraction,” Adv. X-Ray Anal. 26, 1–10.Google Scholar
Soedin, K., Syukran, O., Fadillah, A., and Sidabutar, P. (1985). “Comparison between the efficacy of a single dose of secnidazole with a 5-day course of tetracycline and clioquinol in the treatment of acute intestinal amebiasis,” Pharmaceutica 4, 251–254.Google Scholar
Well, J. L. (1987). Pharmaceutical Preformulation: The Physicochemical Properties of Drug Substances (Wiley, New York).Google Scholar
Werner, P. E., Eriksson, L., and Westdahl, M. (1985). “TREOR, a semi-exhaustive trial-and-error powder indexing program for all symmetries,” J. Appl. Crystallogr. 18, 367–370.CrossRefGoogle Scholar