Urea co-inclusion compounds of glipizide for the improvement of dissolution profile
Tóm tắt
In the present study, urea, a well-known adductor for linear compounds was successfully utilized for inclusion of glipizide—a highly substituted cyclic organic compound through a modified technique. Formation of glipizide co-inclusion compounds in urea was confirmed by FTIR, DSC and XRD. The minimum proportion of rapidly adductible endocyte (RAE) required for adduction of glipizide in urea was estimated by a modified Zimmerschied calorimetric method. Urea–GLP–RAE inclusion compounds containing varying proportions of guests were prepared and their thermal behaviour studied by DSC. The co-inclusion compounds were found to exhibit good content uniformity. Through the formation of co-inclusion compounds of urea, it was possible to achieve steep improvement in the dissolution efficiency of glipizide, which is a BCS class II drug.
Tài liệu tham khảo
D’Onofrio, F., Pempinello, R., Romis, L.: Clinical and metabolic observations with a new synthetic oral antidiabetic agent, Glipizide. Arzneimittelforschung 2(11), 1879–1881 (1972).
Brogden, R.N., Heel, R.C., Pakes, G.E., Speight, T.M., Avery, G.S.: Glipizide: a review of its pharmacological properties and therapeutic use. Drugs 18, 329–353 (1979).
Jamzad, S., Fassihi, R.: Role of surfactant and pH on dissolution properties of fenofibrate and glipizide—a technical note. AAPS PharmSciTech. 7, E1–E6 (2006).
Food and Drug Administration (FDA) Center for Drug Evaluation and Research (CDER). Chemistry review for metaglip tablets. Available at http://www.fda.gov/cder/foi/nda/2002/21–460_metaglip_Chemr.pdf. Accessed:March 29, 2007.
Gidwani, S.K., Singnurkar, P., Tiwari, P.K.: Glipizide-cyclodextrin inclusion compounds and their pharmaceutical compositions. US Patent 6,464,988 B1, 15 Oct 2002.
Himasankar, K., Murali, M.B., Krishna, B.P.S.S., Prasad, D.S., Rao, L.N., Raman, K.V.: Studies on solid dispersion systems of glipizide. Indian J. Pharm. Sci. 64(5), 433–439 (2002).
Aly, A.M., Qato, M.K., Ahmad, M.O.: Enhancement of the dissolution rate and bioavalability of glipizide through cyclodextrin inclusion complex. Pharm. Technol. 27, 54–62 (2003).
Madan, A.K.: Microencapsulation of low dose drugs. Ph.D. Thesis, IIT Delhi (1994).
Thakral, S., Madan, A.K.: Indian Provisional patent “Urea based inclusion complexes of nicorandil, carvidilol, gliclazide and glipizide and the processes thereof.” Indian Patent Application Number 208/DEL/2007 filed on 01/02/2007 (2007).
Harris, K.D.M.: Meldola Lecture: understanding properties of urea and thiourea inclusion compounds. Chem. Soc. Rev. 26, 279–289 (1997).
Smith, A.E.: The crystal structure of urea–hydrocarbon complexes. Acta Crystallogr. 5, 224–235 (1952).
Bishop, R., Dance, I.G.: New type of helical inclusion networks. Top.Curr. Chem. 149, 139–188 (1988).
Frank, S.G.: Inclusion compounds. J. Pharm. Sci. 64, 1585–1604 (1975).
Takemoto, K., Sonoda N.: Inclusion compounds of urea, thiourea and selenourea. In: Atwood, J.L., Davis, J.E.D., MacNicol, D.D. (eds.) Inclusion Compounds, vol. 2. pp. 47–67. Academic Press, London (1984).
Harris, K.D.M., Thomas, J.M.: Structure aspects of urea inclusion compounds and their investigations by X-ray diffraction: a general discussion. J. Chem. Soc., Faraday Trans. 86, 2985–2996 (1990).
Hollingsworth, M.D., Harris, K.D.M.: Urea inclusion compounds. In: Atwood, J.L., Davis, J.E.D., MacNicol, D.D., Vogtle, F, (eds.) Comprehensive Supramolecular Chemistry. Solid State Supramolecular Chemistry—Crystal Engineering, vol. 6, pp. 177–237. Pergamon Press, Oxford (1996).
Smart, S.S., Baghdagi, A.E., Guillaume, F., Harris, K.D.M.: Conformational and vibrational properties of α,ω-dihalogenoalkane/urea inclusion compounds: a Raman scattering investigation. J. Chem. Soc., Faraday Trans. 90, 1313–1322 (1994).
Schiessler, R.W., Flitter, D.: Urea and thiourea adduction of C5-C42-Hydrocarbons. J. Am. Chem. Soc. 74, 1720–1723 (1954).
Harris, K.D.M.: Urea inclusion compounds. In Atwood, J.L., Steed, J.W. (eds.) Encyclopedia of Supramolecular Chemistry, vol. 2, pp. 1538–1549. Marcel Dekker, New York (2004).
Findlay, R.A. Adductive crystallization. In: Schoen, H.M., Mcketta, J.J. (eds.) New Chemical Engineering Separation Techniques, pp. 257–318. Interscience Publishers, New York (1962).
Schlenk, W.: Urea addition of aliphatic compounds. Justus Liebigs Ann. Chem. 565, 204–240 (1949).
Thakral, S., Madan, A.K.: Adduction of amiloride hydrochloride in urea through a modified technique for the dissolution enhancement. J. Pharm. Sci. DOI. 10.1002/jps (2007).
Thakral, S., Madan, A.K.: Urea inclusion compounds of enalapril maleate for the improvement of pharmaceutical characteristics. J. Pharm. Phamcol. (2007, in press).
Madan, A.K., Grover, P.D.: A process for preparation of urea based inclusion compounds of vitamin A esters. Indian Patent 180627, 20 January 1993.
Bajaj, V., Madan, A.K.: A process for preparation of urea complexes of vitamin E and its esters. Indian Patent 182620, 24 October 1994.
Zimmerschied, W.J., Dinnerstein, R.A., Weitkamp, A.W., Marschner, R.F.: Crystalline adducts of urea with linear aliphatic compounds. Ind. Eng. Chem. 42, 1300–1306 (1950).
Moffat, A.C., Osselton, M.D., Widdop, B., Galichet L.Y.: Clarke’s Analysis of Drugs and Poisons, 3rd edn. The Pharmaceutical Press, Glipizide, London 1081–1082 (2003).
Fischer, P.H.H., McDowell, C.A.: The infrared absorption spectra of urea-hydrocarbon adduct. Can. J. Chem. 38, 187–193 (1960).
Durie, R.A., Harrisson, R.J.: Effect of urea-adduct formation and physical state on the infrared spectra of n-paraffin hydrocarbons. Spectrochem. Acta 18, 1505–1514 (1962).
Keller, W.E.: Evidence of planer structure of urea. J. Chem. Phys. 16, 1003–1004 (1948).
McAdie, M.G.: Thermal decomposition of molecular complexes. Can. J. Chem. 41, 2144–2153 (1963).
White, M.A.: Origins of thermodynamic stability of urea: alkane inclusion compounds. Can. J. Chem. 76, 1695–1698 (1988).
Radell, J., Connolly, J.W.: Urea complexes of partially fluorinated esters. J. Org. Chem. 25, 1202–1206 (1960).
Burley, J.C.: Structure and intermolecular interactions of glipizide from laboratory X-ray powder diffraction. Acta Cryst. B61, 710–716 (2005).
Brodman, B.W., Radell, J.: X-ray powder diffraction patterns of some n-alkanone urea inclusion compounds. Separation Sci. 2, 139–142 (1967).
Radell, J., Brodman, B.W.: Urea inclusion compounds of alkenoic acids and alkyl alkenoates. Can. J. Chem. 43, 304–305 (1965).
Radell, J., Connolly J.W.: Determination of relative stability of urea complexes from X-ray powder diffraction data. In: Muller, W.M. (ed.) Advances in X-ray Analysis, vol. 4, pp. 140–150. Plenum Press, New York (1961).
Khan, K.A.: The concept of dissolution efficiency. J. Pharm. Pharmacol. 27, 48–49 (1975).