Chemical reactivity in solid-state pharmaceuticals: Formulation implications

Advanced Drug Delivery Reviews

Volumn 48, Issue 1, 2001, Pages 115-136

  Byrn, Stephen R ^a   Xu, Wei ^b   Newman, Ann W ^c  

^a PURDUE UNIVERSITY   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c SSCI Incorporated   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDRATION; ENZYMES; GLASS TRANSITION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; SOLID STATE PHYSICS; VITAMINS; X RAY CRYSTALLOGRAPHY;

CHEMICAL REACTIVITY;

DRUG PRODUCTS;

ACETIC ACID; ACETYLSALICYLIC ACID; ALANINE; CODEINE; DEXTRAN; DIPEPTIDYL CARBOXYPEPTIDASE; EXCIPIENT; FLUOXETINE; FORMYLMETHIONYLLEUCYLPHENYLALANINE; GLUCOSE; GLYCEROL; HYDROCORTISONE DERIVATIVE; IBUPROFEN; METENKEPHALIN; METHIONINE; METHYL GROUP; MOEXIPRIL; PEPTIDE DERIVATIVE; PHENYLEPHRINE; POLYVINYL ALCOHOL; POVIDONE; PREDNISOLONE DERIVATIVE; QUINAPRIL; RETINOL; SPIRAPRIL; SUCROSE; TARTARIC ACID; TREHALOSE; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG STABILITY; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS; SOLID STATE; TECHNIQUE; WATER ABSORPTION;

CHEMISTRY, PHARMACEUTICAL; EXCIPIENTS; MAILLARD REACTION; OXIDATION-REDUCTION; PEPTIDES; STEROIDS; VITAMIN A;

EID: 0035897596     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(01)00102-8     Document Type: Article

References (46)

1. Morawetz H. Reactivity of organic crystals. Science. 152:1966;705-711.
2. Paul I.C., Y Curtin D. Thermally induced organic reactions in the solid-state. Acc. Chem. Res. 6:1973;217-225.
3. Byrn S.R., Lin C.T. The effect of crystal packing and defects on desolvation of hydrate crystals of caffeine and L-(-)-1,4-cyclohexadiene-1-alanine. J. Am. Chem. Soc. 98:1976;4004-4005.
4. Byrn S.R., Kessler D.W. The solid-state reactivity of the crystal forms hydrocortizone esters. Tetrahedron. 43:1987;1335-1343.
5. Byrn S.R., Sutton P.A., Tobias B., Frye J., Main P. Crystal structure, solid-state NMR spectra, and oxygen reactivity of five crystal forms of prednisolone tertbutylacetate. J. Am. Chem. Soc. 110:1988;1609-1614.
6. Ahlneck C., Zografi G. The molecular basis of moisture effects on the physical and chemical stability of drugs in the solid-state. Int. J. Pharm. 62:1990;87-95.
7. Trueblood K.N., Dunitz J.D. Internal molecular motions in crystals. The estimation of force constants, frequencies and barriers from diffraction data. A feasibility study. Acta Crystallogr., Sect. B, Struct. Sci. B39:1983;120-133.
8. Trueblood K.N. Vibrational parameters in crystals: rigid and non-rigid molecules. J. Mol. Struct. 130:1985;103-115.
9. Dunitz J.D., Maverick E.F., Trueblood K.N. Atomic movements in molecular crystals from diffraction measurements. Angew. Chem. Int. Ed. Engl. 27:1988;880-895.
10. Dunitz J.D., Schomaker V., Trueblood K.N. Interpretation of atomic displacement parameters from diffraction studies of crystals. J. Phys. Chem. 92:1988;856-867.
11. Finkel'shtein E.I., Alekseev E.V., Kozlov E.I. Kinetic relationships of the solid-state autooxidation of β-carotene. J. Org. Chem. (Russia), Eng. Trans. 10:1974;1037-1043.
12. Baxter J.G., Robeson C.E. Crystalline aliphatic esters of vitamin A. J. Am. Chem. Soc. 64:1942;2407-2410.
13. Guillory J.K., Higuchi T. Solid-state stability of some crystalline vitamin A compounds. J. Pharm. Sci. 51:1962;100-105.
14. Adamski R., Dobrucki R. Carbonyl products of decomposition of vitamin A palmitate concentrated preparations. Farm. Pol. 27:1971;353-355.
15. Bhattacharya S. Vitamin A complexes. IV. Influence of intact and hydrolyzed proteins in solid-state. J. Inst. Chem., Calcutta. 41:1969;147-153.
16. Leszczyn̄ska-Bakal H., Siedlanowska-Krówczyn̄ska H. Preparation of dry (powdered) stabilized vitamin A pharmaceuticals. Cesk Farm. 19:1970;109-111.
17. Kitaigorodskii A.I. Organic Chemical Crystallography. 1961;Consultants Bureau, New York, NY.
18. W. Xu, Investigation of solid-state stability of selected bioactive compounds. Ph.D. Thesis, Purdue University, West Lafayette, IN 47907-1333, 1997.
19. Brenner G., Roberts F.E., Hoinowski A., Budavari J., Powell B., Hinkley D., Schoenewaldt E. Effect of crystalline form on the air-oxidation of steroidal 11β-ols to 11-ones. Angew. Chem., Int. Ed. Engl. 8:1969;975-976.
20. Lewbart M.L. Spontaneous oxidation of steroidal 11β-ols to 11-ketones in the crystalline state. Nature. 222:1969;663-664.
21. Lin C.T., Perrier P., Clay G.G., Sutton P.A., Byrn S.R. Solid-state photooxidation of 21-cortisol tert-butylacetate to 21-cortisone tert-butylacetate. J. Org. Chem. 47:1982;2978-2981.
22. Ressler C. Solid-state dehydrogenation of L-1,4-cyclohexadiene-1-alanine hydrate to L-phenylalanine. J. Org. Chem. 37:1972;2933-2936.
23. Weeks C.M., Duax W.L. The crystal and molecular structure of two 9α-fluoro-2α-methyl steroids. Acta Crystallogr., Sect. B. B32:1976;2819-2825.
24. D.W. Kessler, Polymorphs of hydrocortisone 21-esters: their characterization and solid-state reactivity. Ph.D. Thesis, Purdue University, West Lafayette, IN 47907-1333, 1986.
25. A.L.J. Beckwith, The oxidation of crystalline cholesterol, Proc. Chem. Soc. 194-195 (1958).
26. Hausin R.J., Codding P.W. Molecular and crystal structures of MDL27,467A hydrochloride and quinapril hydrochloride, two ester derivatives of potent angiotensin converting enzyme inhibitors. J. Med. Chem. 34:1991;511-517.
27. Guo Y., Byrn S.R., Zografi G. Physical characteristics and chemical degradation of amorphous quinapril. J. Pharm. Sci. 89:2000;241-249.
28. Gu L., Strickley R.G., Chi L.H., Chowhan Z.T. Drug-excipient incompatibility studies of the dipeptide angiotensin-converting enzyme inhibitor, moexipril hydrochloride: dry powder vs. wet granulation. Pharm. Res. 7:1990;379-383.
29. Strickley R.G., Visor G.C., Lin L., Gu L. An unexpected pH effect on the stability of moexipril lyophilized powder. Pharm. Res. 6:1989;971-975.
30. Lai M.C., Hageman M.J., Schowen R.L., Borchardt R.L., Topp E.M. Chemical stability of peptides in polymers. 1. Effect of water on peptide deamidation in poly(vinyl alcohol) and poly(vinyl pyrrolidone) matrixes. J. Pharm. Sci. 88:2000;1073-1080.
31. Lai M.C., Hageman M.J., Schowen R.L., Borchardt R.L., Laird B.B., Topp E.M. Chemical stability of peptides in polymers. 2. Discriminating between solvent and plasticizing effects of water on peptide deamination in poly(vinylpyrrolidone). J. Pharm. Sci. 88:2000;1081-1089.
32. Allison S.D., Manning M.C., Randolph T.W., Middleton K., Davis A., Carpenter J.F. Optimization of storage stability of lyophilized actin using combinations of disaccharides and dextran. J. Pharm. Sci. 89:2000;199-214.
33. Troup A.E., Mitchner H. Degradation of phenylephrine hydrochloride in tablet formulations containing aspirin. J. Pharm. Sci. 53:1964;375-379.
34. Jacobs A.L., Dilatush A.E., Weinstein S., Windheuser J.J. Formation of acetylcodeine from aspirin and codeine. J. Pharm. Sci. 55:1966;893-895.
35. Koshy K.T., Troup A.E., Duvall R.N., Conwell R.N., Shankle L.L. Acetylation of acetaminophen in tablet formulations containing aspirin. J. Pharm. Sci. 56:1967;1117-1121.
36. Wirth D.D., Baertschi S.W., Johnson R.A., Maple S.R., Miller M.S., Hallenbeck D.K., Gregg S.M. Maillard Reaction of lactose and fluoxetine hydrochloride, a secondary amine. J. Pharm. Sci. 87:1998;31-39.
37. David S.T., Gallian C.E. Drug Dev. Ind. Pharm. 12:(14):1986;2541-2550.
38. Usui F., Carstensen J.T. Interactions in the solid-state. I. Interactions of sodium bicarbonate and tartaric acid under compressed conditions. J. Pharm. Sci. 74:1985;1293-1297.
39. Wright J.L., Carstensen J.T. Interactions in the solid-state. II. Interaction of sodium bicarbonate with substituted benzoic acids in the presence of moisture. J. Pharm. Sci. 75:1986;546-551.
40. Lin C.T., Siew P.Y., Byrn S.R. Solid-state dehydrochlorination and decarboxylation reactions. I. Reactions of p-aminosalicylic acid hydrochloride and p-aminosalicylic acid, revised crystal structure of p-aminosalicylic acid. J. Chem. Soc. Perkin Trans. 2:1978;975-982.
41. Kararli T.T., Needham T.E., Seul C.J., Finnegan P.M. Solid-state interaction of magnesium oxide and ibuprofen to form a salt. Pharm. Res. 6:1989;804-808.
42. G.A. Stephenson, Solid-state investigations of selected pharmaceutical compounds. Ph.D. Thesis, Purdue University, West Lafayette, IN 47907-1333, 1994.
43. 2 Ibuprofen or prufen. Cryst. Struct. Comm. 3:1974;73-75.
44. Freer J.M., Bunyan N., Shankland N., Sheen D.B. Structure of (S)-(+)-ibuprofen. Acta Crystallogr., Section C. C49:1993;1378-1380.
45. Guo Y., Byrn S.R., Zografi G. Physical characteristics and chemical degradation of amorphous quinapril hydrochloride. J. Pharm. Sci. 89:2000;128-143.
46. Y. Guo, S.R. Byrn, G. Zografi, Effects of lyophilization on the physical and chemical stability of amorphous quinapril hydrochloride, Pharm. Res., in press (2000).