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Volumn 99, Issue 9, 2010, Pages 3839-3848

Crystal quality and physical reactivity in the case of flufenamic acid (FFA)

Author keywords

AFM; Crystal defects; Crystal growth; Crystallization; Etching pattern; Flufenamic acid; Micrograph; Polymorph; Solid state transformation

Indexed keywords

FLUFENAMIC ACID;

EID: 77956387423     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22221     Document Type: Article
Times cited : (14)

References (56)
  • 1
    • 0001184876 scopus 로고    scopus 로고
    • Q6A Specifications, Test procedures and acceptance criteria for new drug and hew drug products: Chemical substances
    • 1997. Q6A Specifications, Test procedures and acceptance criteria for new drug and hew drug products: Chemical substances. Fed Reg 62:62889-62910.
    • (1997) Fed Reg , vol.62 , pp. 62889-62910
  • 2
    • 0029070763 scopus 로고
    • Pharmaceutical solids: A strategic approach to regulatory considerations
    • Byrn S, Pfeiffer R, Ganey M, Hoiberg C, Poochikian G. 1995. Pharmaceutical solids: A strategic approach to regulatory considerations. Pharm Res 12:945-954.
    • (1995) Pharm Res , vol.12 , pp. 945-954
    • Byrn, S.1    Pfeiffer, R.2    Ganey, M.3    Hoiberg, C.4    Poochikian, G.5
  • 3
    • 0032104268 scopus 로고    scopus 로고
    • Physical characterization of polymorphic drugs: An integrated characterization strategy
    • Yu L, Reutzel SM, Stephenson GA. 1998. Physical characterization of polymorphic drugs: An integrated characterization strategy. Sci Pharm 1:118-127.
    • (1998) Sci Pharm , vol.1 , pp. 118-127
    • Yu, L.1    Reutzel, S.M.2    Stephenson, G.A.3
  • 5
    • 0025260568 scopus 로고
    • Le Polymorphisme des Excipients
    • Giron D. 1990. Le Polymorphisme des Excipients. STP Pharma 6:87-98.
    • (1990) STP Pharma , vol.6 , pp. 87-98
    • Giron, D.1
  • 6
    • 0023979166 scopus 로고
    • The crystal structure, solid-state NMR spectra, and oxygen reactivity of five crystal forms of prednisolone tert-butylacetate
    • Byrn SR, Sutton PA, Tobias B, Frye J, Main P. 1988. Crystal structure, solid-state NMR spectra, and oxygen reactivity of five crystal forms of predisolone tert-butylacetate. J Am Chem Soc 110:1609-1614. (Pubitemid 18066749)
    • (1988) Journal of the American Chemical Society , vol.110 , Issue.5 , pp. 1609-1614
    • Byrn, S.R.1    Sutton, P.A.2    Tobias, B.3    Frye, J.4    Main, P.5
  • 8
    • 3142558224 scopus 로고    scopus 로고
    • Crystal packing and chemical reactivity of two polymorphs of flufenamic acid with ammonia
    • Chen XM, Li TL, Morris KR, Byrn SR. 2002. Crystal packing and chemical reactivity of two polymorphs of flufenamic acid with ammonia. Mol Cryst Liq Cryst 381:121-131.
    • (2002) Mol Cryst Liq Cryst , vol.381 , pp. 121-131
    • Chen, X.M.1    Li, T.L.2    Morris, K.R.3    Byrn, S.R.4
  • 9
    • 2842537959 scopus 로고
    • Recent insights into dehydration reactions of crystalline solids
    • Galway AK, Laverty GM. 1990. Recent insights into dehydration reactions of crystalline solids. J Chim Phys-Chim Biol 87:1207-1221.
    • (1990) J Chim Phys-Chim Biol , vol.87 , pp. 1207-1221
    • Galway, A.K.1    Laverty, G.M.2
  • 10
    • 0001317352 scopus 로고    scopus 로고
    • Mechanism of several solid-solid transformations between dehydrated and anhydrous copper (II) 8-hydroxyquinolinates. Proposition for a unified model for the dehydration of molecular crystals
    • Petit S, Coguerel G. 1996. Mechanism of several solid-solid transformations between dehydrated and anhydrous copper (II) 8-hydroxyquinolinates. Proposition for a unified model for the dehydration of molecular crystals. Chem Mater 8:2247-2258.
    • (1996) Chem Mater , vol.8 , pp. 2247-2258
    • Petit, S.1    Coguerel, G.2
  • 11
    • 0018113044 scopus 로고
    • Molecular mechanism of polymorphic transitions
    • Mnyukh YV. 1979. Molecular mechanism of polymorphic transitions. Mol Cryst Liq Cryst 52:163.
    • (1979) Mol Cryst Liq Cryst , vol.52 , pp. 163
    • Mnyukh, Y.V.1
  • 12
    • 0026624271 scopus 로고
    • Internal structure rebuilding reactions of crystalline and amorphous solids
    • Stoch L. 1992. Internal structure rebuilding reactions of crystalline and amorphous solids. J Thermal Anal 38:131-139.
    • (1992) J Thermal Anal , vol.38 , pp. 131-139
    • Stoch, L.1
  • 13
    • 0006896549 scopus 로고
    • Study of a possible reaction pathway in the polymorphic transformation of diacetamide
    • Bayard F, Decoret C, Royer J, Smeyers YG, Randez JJ. 1988. Study of a possible reaction pathway in the polymorphic transformation of diacetamide. Int J Quantum Chem 33:61-68.
    • (1988) Int J Quantum Chem , vol.33 , pp. 61-68
    • Bayard, F.1    Decoret, C.2    Royer, J.3    Smeyers, Y.G.4    Randez, J.J.5
  • 15
    • 0027375709 scopus 로고
    • Effects of environmental temperature and compression energy on polymorphic transformation during tabletting
    • Otsuka M, Matsuda Y. 1993. Effects of environmental temperature and compression energy on polymorphic transformation during tabletting. Drug Dev Ind Pharm 19:2241-2269.
    • (1993) Drug Dev Ind Pharm , vol.19 , pp. 2241-2269
    • Otsuka, M.1    Matsuda, Y.2
  • 16
    • 0027589718 scopus 로고
    • A theoretical study of the first order γ-α and α-β phase transitions of dichlorobenzene
    • Royer J, Skalli M, Bayard F, Decoret C. 1993. A theoretical study of the first order γ-α and α-β phase transitions of dichlorobenzene. J Cryst Growth 130:280-286.
    • (1993) J Cryst Growth , vol.130 , pp. 280-286
    • Royer, J.1    Skalli, M.2    Bayard, F.3    Decoret, C.4
  • 17
    • 0026763720 scopus 로고
    • Some recent studies of the mechanisms of dehydration reactions of solids
    • Galwey AK. 1992. Some recent studies of the mechanisms of dehydration reactions of solids. J Thermal Anal 38:99-110.
    • (1992) J Thermal Anal , vol.38 , pp. 99-110
    • Galwey, A.K.1
  • 18
    • 84914263659 scopus 로고
    • Kinetics and mechanism of the dehydration of crystal hydrates
    • Lyakhov NZ, Boldyrev VV. 1972. Kinetics and mechanism of the dehydration of crystal hydrates. Russ Chem Rev 41:919-928.
    • (1972) Russ Chem Rev , vol.41 , pp. 919-928
    • Lyakhov, N.Z.1    Boldyrev, V.V.2
  • 19
    • 0016227738 scopus 로고
    • Drugs which inhibit prostaglandin biosynthesis
    • Flower RJ. 1974. Drugs which inhibit prostaglandin biosynthesis. Pharmacol Rev 26:33.
    • (1974) Pharmacol Rev , vol.26 , pp. 33
    • Flower, R.J.1
  • 21
    • 0016132589 scopus 로고
    • On polymorphism of drugs: Flufenamic acid and BL 191
    • author's transl
    • Kuhnert-Brandstatter M, Borka L, Friedrich-Sander G. 1974. On polymorphism of drugs: Flufenamic acid and BL 191 (author's transl). Arch Pharm 307:845-853.
    • (1974) Arch Pharm , vol.307 , pp. 845-853
    • Kuhnert-Brandstatter, M.1    Borka, L.2    Friedrich-Sander, G.3
  • 22
    • 0347494162 scopus 로고
    • Polymorphic transitions in crystals: Nucleation
    • Mnyukh YV. 1976. Polymorphic transitions in crystals: Nucleation. J Cryst Growth 32:371-377.
    • (1976) J Cryst Growth , vol.32 , pp. 371-377
    • Mnyukh, Y.V.1
  • 23
    • 0024807207 scopus 로고
    • Influence of compaction on the intrinsic dissolution rate of modified acetaminophen and adipic acid crystals
    • Chan HK, Grant DJW. 1989. Influence of compaction on the intrinsic dissolution rate of modified acetaminophen and adipic acid crystals. Int J Pharm 57:117-124.
    • (1989) Int J Pharm , vol.57 , pp. 117-124
    • Chan, H.K.1    Grant, D.J.W.2
  • 24
    • 0021821356 scopus 로고
    • Modification of acetaminophen crystals: Influence of growth in aqueous solutions containing p-acetoxyacetanilide on crystal properties
    • Chow AHL, Chow PKK, Zhongshan W, Grant DJW. 1985. Modification of acetaminophen crystals: Influence of growth in aqueous solutions containing p-acetoxyacetanilide on crystal properties. Int J Pharm 25:239-258.
    • (1985) Int J Pharm , vol.25 , pp. 239-258
    • Chow, A.H.L.1    Chow, P.K.K.2    Zhongshan, W.3    Grant, D.J.W.4
  • 25
    • 0021239020 scopus 로고
    • Modification of adipic acid crystals: Influence of growth in the presence of fatty acid additives on crystal properties
    • Chow KY, Go J, MehdizadehM, Grant DJW. 1984. Modification of adipic acid crystals: Influence of growth in the presence of fatty acid additives on crystal properties. Int J Pharm 20:3-24. (Pubitemid 14091705)
    • (1984) International Journal of Pharmaceutics , vol.20 , Issue.1-2 , pp. 3-24
    • Chow, K.Y.1    Go, J.2    Mehdizadeh, M.3    Grant, D.J.W.4
  • 26
    • 0021797830 scopus 로고
    • Modification of adipic acid crystals II: Influence of growth in the presence of oleic acid additives on crystal properties
    • Chow KY, Go J, Wang Z, Mehdizadeh M, Grant DJW. 1985. Modification of adipic acid crystals II: Influence of growth in the presence of oleic acid additives on crystal properties. Int J Pharm 25:41-55.
    • (1985) Int J Pharm , vol.25 , pp. 41-55
    • Chow, K.Y.1    Go, J.2    Wang, Z.3    Mehdizadeh, M.4    Grant, D.J.W.5
  • 27
    • 0027272306 scopus 로고
    • Effect of the opposite enantiomer on the physicochemical properties of (-)-ephedrinium 2-naphthalenesulfonate crystals
    • Duddu SP, Fung FKY, Grant DJW. 1994. Effect of the opposite enantiomer on the physicochemical properties of (-)-ephedrinium 2-naphthalenesulfonate crystals. Int J Pharm 94:171-179.
    • (1994) Int J Pharm , vol.94 , pp. 171-179
    • Duddu, S.P.1    Fung, F.K.Y.2    Grant, D.J.W.3
  • 28
    • 1442353033 scopus 로고
    • Lattice imperfections in organic solids
    • Thomas JM, Renshaw GD. 1967. Lattice imperfections in organic solids. Trans Farad Soc 63:1922-1928.
    • (1967) Trans Farad Soc , vol.63 , pp. 1922-1928
    • Thomas, J.M.1    Renshaw, G.D.2
  • 29
    • 0008047791 scopus 로고
    • X-ray topographic investigations of solid state reactions. I. Changes in surface and bulk structure during incipient thermal decomposition in sodium chlorate monocrystals
    • Begg ID, Halfpenny PJ, Hooper RM, Narang RS, Roberts KJ, Sherwood JN. 1983. X-ray topographic investigations of solid state reactions. I. Changes in surface and bulk structure during incipient thermal decomposition in sodium chlorate monocrystals. Proc Roy Soc Lond A386:431-442.
    • (1983) Proc Roy Soc Lond , vol.A386 , pp. 431-442
    • Begg, I.D.1    Halfpenny, P.J.2    Hooper, R.M.3    Narang, R.S.4    Roberts, K.J.5    Sherwood, J.N.6
  • 30
    • 0017857869 scopus 로고
    • Quantitative crystallinity determinations for β-lactam antibiotics by solution calorimetry: Correlations with stability
    • Pikal MJ, Lukes AL, Lang JE, Gaines K. 1978. Quantitative determination for β-lactam antibiotics by solution calorimetry: Correlation with stability. J Pharm Sci 67:767-772. (Pubitemid 8355230)
    • (1978) Journal of Pharmaceutical Sciences , vol.67 , Issue.6 , pp. 767-773
    • Pikal, M.J.1    Lukes, A.L.2    Lang, J.E.3    Gaines, K.4
  • 31
    • 0022354180 scopus 로고
    • The effect of mechanical comminution on drug stability
    • Waltersson JO, Lundgren P. 1985. The effect of mechanical comminution on drug stability. Acta Pharm Suecica 22:291-300.
    • (1985) Acta Pharm Suecica , vol.22 , pp. 291-300
    • Waltersson, J.O.1    Lundgren, P.2
  • 32
    • 0031440211 scopus 로고    scopus 로고
    • Electron and light microscopial investigation of defect structures in mesophases of pharmaceutical substances
    • Rades T, Muller-Goymann CC. 1997. Electron and light microscopial investigation of defect structures in mesophases of pharmaceutical substances. Colloid Polym Sci 275:1169-1178.
    • (1997) Colloid Polym Sci , vol.275 , pp. 1169-1178
    • Rades, T.1    Muller-Goymann, C.C.2
  • 33
    • 34249024184 scopus 로고    scopus 로고
    • Applications of image analysis for the quantitative characterization of microstructural defects in materials
    • Exner HE, Rettenmayr M. 1997. Applications of image analysis for the quantitative characterization of microstructural defects in materials. Inst Phys Conf Ser No 160:237-244.
    • (1997) Inst Phys Conf Ser , Issue.160 , pp. 237-244
    • Exner, H.E.1    Rettenmayr, M.2
  • 34
    • 0024167049 scopus 로고
    • The use of calorimetric data for estimation of the point defect concentration in solids
    • Uvarov NF, Hairetdinov EF. 1988. The use of calorimetric data for estimation of the point defect concentration in solids. J Thermal Anal 33:279-284.
    • (1988) J Thermal Anal , vol.33 , pp. 279-284
    • Uvarov, N.F.1    Hairetdinov, E.F.2
  • 35
    • 38249018928 scopus 로고
    • The use of conformational disorder by thermal analysis
    • Wunderlich B. 1990. The use of conformational disorder by thermal analysis. Thermochim Acta 162:59-67.
    • (1990) Thermochim Acta , vol.162 , pp. 59-67
    • Wunderlich, B.1
  • 36
    • 0022658194 scopus 로고
    • A disruption index for quantifying the solid state disorder induced by additives or impurities. II. Evaluation from heat of solution
    • DOI 10.1016/0378-5173(86)90233-4
    • Grant DJW, York P. 1986. A disruption index for quantifying the solid state disorder induced by additives or impurities. II Evaluation from heat of solution. Int J Pharm 28:103-112. (Pubitemid 16187085)
    • (1986) International Journal of Pharmaceutics , vol.28 , Issue.2-3 , pp. 103-112
    • Grant, D.J.W.1    York, P.2
  • 37
    • 77956381073 scopus 로고
    • Solid-state disorder in drugs and excipients
    • York P, Grant DJW. 1986. Solid-state disorder in drugs and excipients. Anal Proc 23:396-397.
    • (1986) Anal Proc , vol.23 , pp. 396-397
    • York, P.1    Grant, D.J.W.2
  • 38
    • 0000847179 scopus 로고
    • The use of thermal analysis in the assessment of crystal disruption
    • Duddu SP, Grant DJW. 1995. The use of thermal analysis in the assessment of crystal disruption. Thermochim Acta 248:131-145.
    • (1995) Thermochim Acta , vol.248 , pp. 131-145
    • Duddu, S.P.1    Grant, D.J.W.2
  • 39
    • 0001154894 scopus 로고
    • Crystal defects and dissolution
    • Burt H, Mitchell AG. 1981. Crystal defects and dissolution. Int J Pharm 9:137-152.
    • (1981) Int J Pharm , vol.9 , pp. 137-152
    • Burt, H.1    Mitchell, A.G.2
  • 40
    • 0032689290 scopus 로고    scopus 로고
    • The relationship between crystal growth and defect structure: A study of potassium hydrogen phthalate using x-ray topography and atomic force microscopy
    • Ester GR, Price R, Halfpenny PJ. 1999. The relationship between crystal growth and defect structure: A study of potassium hydrogen phthalate using x-ray topography and atomic force microscopy. J Appl Phys B 32:A128-A132.
    • (1999) J Appl Phys B , vol.32
    • Ester, G.R.1    Price, R.2    Halfpenny, P.J.3
  • 42
    • 0033639595 scopus 로고    scopus 로고
    • Polymorphic discrimination using atomic force microscopy: Distinguishing between two polymorphs of the drug cimetidine
    • DOI 10.1021/la990470a
    • Danesh A, Chen X, Davies MC, Roberts CJ, Sanders GH, Tendler SJB, Williams PM. 2000. Polymorphic discrimination using atomic force microscopy: Distinguishing between two polymorphs of the drug cimetidine. Langmuir 16:866-870. (Pubitemid 32211296)
    • (2000) Langmuir , vol.16 , Issue.2 , pp. 866-870
    • Danesh, A.1    Chen, X.2    Davies, M.C.3    Roberts, C.J.4    Sanders, G.H.W.5    Tendler, S.J.B.6    Williams, P.M.7    Wilkins, M.J.8
  • 43
    • 3242673240 scopus 로고    scopus 로고
    • AFM studies of the crystallization and habit modification of an excipient material, adipic acid
    • Keel TR, Thompson C, Davis MC, Tendler SJB, Roberts CJ. 2004. AFM studies of the crystallization and habit modification of an excipient material, adipic acid. Int J Pharm 280:185-198.
    • (2004) Int J Pharm , vol.280 , pp. 185-198
    • Keel, T.R.1    Thompson, C.2    Davis, M.C.3    Tendler, S.J.B.4    Roberts, C.J.5
  • 45
    • 2942601659 scopus 로고    scopus 로고
    • Nanoscale observations of the effect of cobalt on calcite growth and dissolution
    • Freij SJ, Putnis A, Astilleros JM. 2004. Nanoscale observations of the effect of cobalt on calcite growth and dissolution. J Cryst Growth 267:288-300.
    • (2004) J Cryst Growth , vol.267 , pp. 288-300
    • Freij, S.J.1    Putnis, A.2    Astilleros, J.M.3
  • 46
    • 0033889469 scopus 로고    scopus 로고
    • Nucleation and growth of supported metal clusters at defects sites on oxide and halide (001) surfaces
    • Venables JA, Harding JH. 2000. Nucleation and growth of supported metal clusters at defects sites on oxide and halide (001) surfaces. J Cryst Growth 211:27-33.
    • (2000) J Cryst Growth , vol.211 , pp. 27-33
    • Venables, J.A.1    Harding, J.H.2
  • 47
    • 0033513864 scopus 로고    scopus 로고
    • In situ atomic force microscopy studies of surface morphology, growth kinetics, defect structures and dissolution in macromolecular crystallization
    • Malkin AJ, Kuznetsov YG, McPherson A. 1999. In situ atomic force microscopy studies of surface morphology, growth kinetics, defect structures and dissolution in macromolecular crystallization. J Cryst Growth 196. 471-488.
    • (1999) J Cryst Growth , vol.196 , pp. 471-488
    • Malkin, A.J.1    Kuznetsov, Y.G.2    McPherson, A.3
  • 48
    • 0033516408 scopus 로고    scopus 로고
    • Etch pit study of different crystallographic faces of L-arginine hydrobromide monohydrate (LAHBr) in some organic acids
    • Mukerji S, Kar T. 1999. Etch pit study of different crystallographic faces of L-arginine hydrobromide monohydrate (LAHBr) in some organic acids. J Cryst Growth 204. 341-347.
    • (1999) J Cryst Growth , vol.204 , pp. 341-347
    • Mukerji, S.1    Kar, T.2
  • 49
    • 0033314737 scopus 로고    scopus 로고
    • Effect of different crystal faces on experimental interaction force and aggregation of hematite
    • Hiemstra T, Riemsdijk WH. 1999. Effect of different crystal faces on experimental interaction force and aggregation of hematite. Langmuir 15:8045-8051.
    • (1999) Langmuir , vol.15 , pp. 8045-8051
    • Hiemstra, T.1    Riemsdijk, W.H.2
  • 50
    • 5144221759 scopus 로고    scopus 로고
    • Observation of etch figures on protein crystals by atomic force microscopy
    • Hondoh H, Nakada T. 2004. Observation of etch figures on protein crystals by atomic force microscopy. Jpn J Appl Phys 43:4529-4532.
    • (2004) Jpn J Appl Phys , vol.43 , pp. 4529-4532
    • Hondoh, H.1    Nakada, T.2
  • 51
    • 0017599263 scopus 로고
    • Crystallographic properties of flufenamic acid
    • Krc J, Jr. 1977. Crystallographic properties of flufenamic acid. Microscope 25:31-45.
    • (1977) Microscope , vol.25 , pp. 31-45
    • Krc Jr., J.1
  • 53
    • 0342795498 scopus 로고
    • Structural studies of analgesics and their interactions. IX. Structure of a new crystal form of 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid (flufenamic acid)
    • Krishna MHM, Bhat TN, Vijayan M. 1982. Structural studies of analgesics and their interactions. IX. Structure of a new crystal form of 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid (flufenamic acid). Acta Cryst B38:315-317.
    • (1982) Acta Cryst , vol.B38 , pp. 315-317
    • Krishna, M.H.M.1    Bhat, T.N.2    Vijayan, M.3
  • 54
    • 24344504062 scopus 로고    scopus 로고
    • Understanding solid-state reactions of organic crystals with density functional theory-based concepts
    • Feng S, Li T. 2005. Understanding solid-state reactions of organic crystals with density functional theory-based concepts. J Phys Chem A 109:7528-7563.
    • (2005) J Phys Chem A , vol.109 , pp. 7528-7563
    • Feng, S.1    Li, T.2
  • 55
    • 34249096208 scopus 로고    scopus 로고
    • Investigations on solid-solid phase transformation of 5-methyl-2-[(4- Methyl-2-nitrophenyl)amino]-3-thiophenecarbonitrile
    • DOI 10.1002/jps.20937
    • Li H, Stowell JG, Morris KR, Byrn SR. 2007. Investigations on solids-solid phase transformation of 5-methyl-2-[(4-methyl-2-nitrophenyl)amino]- 3-thiophenicarbonitrile. J Pharm Sci 96:1079-1089. (Pubitemid 46797478)
    • (2007) Journal of Pharmaceutical Sciences , vol.96 , Issue.5 , pp. 1079-1089
    • Li, H.1    Stowell, J.G.2    He, X.3    Morris, K.R.4    Byrn, S.R.5
  • 56
    • 0001759249 scopus 로고    scopus 로고
    • Influence of solvent and crystalline supramolecular structure on the formation of etching patterns on acetaminophen single crystals: A study with atomic force microscopy and computer simulation
    • Li T, Morris KR, Park K. 2000. Influence of solvent and crystalline supramolecular structure on the formation of etching patterns on acetaminophen single crystals: A study with atomic force microscopy and computer simulation. J Phys Chem B 104:2019-2032.
    • (2000) J Phys Chem B , vol.104 , pp. 2019-2032
    • Li, T.1    Morris, K.R.2    Park, K.3


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