Insights into the dehydration behavior of thiamine hydrochloride (vitamin B1) hydrates: Part I

Journal of Pharmaceutical Sciences

Volumn 99, Issue 2, 2010, Pages 816-827

  Chakravarty, Paroma ^a   Berendt, Robert T ^b   Munson, Eric J ^b   Young Jr , Victor G ^c   Govindarajan, Ramprakash ^a   Suryanarayanan, Raj ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF KANSAS   (United States)

^c University of Minnesota   (United States)

Author keywords

Crystal structure; Hydrates; Mobility; Solid state NMR; Spectroscopy; X ray powder diffractometry

Indexed keywords

NONSTOICHIOMETRIC COMPOUND; THIAMINE;

ARTICLE; CRYSTALLOGRAPHY; DESICCATION; DESORPTION; DRUG STRUCTURE; HYDRATION; MICROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROOM TEMPERATURE; SPECTROSCOPY; WATER ABSORPTION; WATER CONTENT;

EID: 74049110430     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21876     Document Type: Article

References (47)

1. Cui Y, Yao E. 2008. Evaluation of hydrate-screening methods. J Pharm Sci 97:2730-2744.
2. Gillon AL, Davey RJ, Storey R, Feeder N, Nichols G, Dent G, Apperley DC. 2005. Solid state dehydration processes: Mechanism of water loss from crystalline inosine dihydrate. J Phys Chem B 109:5341-5347.
3. Khankari RK, Grant DJW. 1995. Pharmaceutical hydrates. Thermochim Acta 248:61-79.
4. Morris KR. 1999. Structural aspects of hydrates and solvates. In: Brittain HG, editor. Polymorphism in pharmaceutical solids. New York: Marcel Dekker. pp. 125-181.
5. Patel NK, Patel IJ, Cutie AJ, Wadke DA, Monkhouse DC, Reier GE. 1988. The effect of selected direct compression excipients on the stability of aspirin as a model hydrolyzable drug. Drug Dev Ind Pharm 14:77-98.
6. Garner WE. 1955. Chemistry of the solid state. New York: Academic Press. pp. 213-231.
7. Brenner G, Roberts FE, Hoinowski A, Budavari J, Powell B, Hinkley D, Schoenewaldt E. 1969. Effect of crystalline form on the air-oxidation of steroidal 11beta -ols to 11-ones. Angew Chem Int Ed Engl 8:975-976.
8. Rani M, Govindarajan R, Surana R, Suryanarayanan R. 2006. Structure in dehydrated trehalose dihydrate-evaluation of the concept of partial crystallinity. Pharm Res 23:2356-2367.
9. Rodriguez-Hornedo N, Lechuga-Ballesteros D, Wu HJ. 1992. Phase transition and heterogeneous/epitaxial nucleation of hydrated and anhydrous theophylline crystals. Int J Pharm 85:149-162.
10. Griesser UJ. 2006. The importance of solvates. In: Hilfiker R, editor. Polymorphism. Weinheim: Wiley-VCH. pp. 211-233.
11. Vippagunta SR, Brittain HG, Grant DJW. 2001. Crystalline solids. Adv Drug Dev Rev 48:3-26.
12. Perrier P, Byrn SR. 1982. Influence of crystal packing on the solid-state desolvation of purine and pyrimidine hydrates: Loss of water of crystallization from thymine monohydrate, cytosine monohydrate, 5-nitrouracil monohydrate, and 20-deoxyadenosine monohydrate. J Org Chem 47: 4671-4676.
13. Han J, Suryanarayanan R. 1997. Applications of pressure differential scanning calorimetry in the study of pharmaceutical hydrates. 1. Carbamazepine dihydrate. Int J Pharm 157:209-218.
14. Lumpkin JA, Perlmutter DD. 1995. Thermal and water vapor effects on the rate of the dehydration reactions of barium chloride. Thermochim Acta 249:335-349.
15. McMahon LE, Timmins P, Williams AC, York P. 1996. Characterization of dihydrates prepared from carbamazepine polymorphs. J Pharm Sci 85:1064-1069.
16. Mimura H, Kitamura S, Kitagawa T, Kohda S. 2002. Characterization of the non-stoichiometric and isomorphic hydration and solvation in FK041 clathrate. Colloids Surf B 26:397-406.
17. Stephenson GA, Diseroad BA. 2000. Structural relationship and desolvation behavior of cromolyn, cefazolin and fenoprofen sodium hydrates Int J Pharm 198:167-177.
18. Cox JSG, Woodard GD, McCrone WC. 1971. Solid-state chemistry of cromolyn sodium (disodium cromoglycate). J Pharm Sci 60:1458-1465.
19. Te RL, Griesser UJ, Morris KR, Byrn SR, Stowell JG. 2003. X-ray diffraction and solid-state NMR investigation of the single-crystal to single-crystal dehydration of thiamine hydrochloride monohydrate. Crys Growth Des 3:997-1004.
20. Watanabe A, Nakamachi H. 1976. Polymorphism of thiamine hydrochloride (author's transl). Yakugaku Zasshi 96:1236-1240.
21. Watanabe A, Tasaki S, Wada Y, Nakamachi H. 1979. Polymorphism of thiamine hydrochloride. II. Crystal structure of thiamine hydrochloride hemihydrate and its stability. Chem Pharm Bull 27:2751-2759.
22. The United States Pharmacopoeia (USP 31). 2008. Thiamine hydrochloride monograph. Rockville, MD: United States Pharmacopoeial Convention.
23. European Pharmacopoeia. 6th Edition (6.5), Thiamine hydrochloride monograph 2009: Directorate for the Quality of Medicines and Healthcare of the Council of Europe.
24. Hellemann MM. 2001. Pulver- und tablettentech-nologische charakterisierung von polymorphen und pseudopolymorphen materialien aus dem bereich der pharmazie. University of Innsbruck: Institute of Pharmacognosy. p. 184.
25. Wostheinrich K, Schmidt PC. 2001. Polymorphic changes of thiamine hydrochloride during granulation and tableting. Drug Dev Ind Pharm 27:481-489.
26. Pines A, Gibby MG, Waugh JS. 1973. Protonenhanced NMR of dilute spins in solids. J Chem Phys 59:569-590.
27. Metz G, Wu X, Smith SO. 1994. Ramped-amplitude cross polarization in magic-angle-spinning NMR. J Magn Reson Ser A 110:219-227.
28. Dixon WT, Schaefer J, Sefcik MD, Stejskal EO, McKay RA. 1982. Total suppression of sidebands in CPMAS carbon-13 NMR. J Magn Reson 49:341-345.
29. Fung BM, Khitrin AK, Ermolaev K. 2000. An improved broadband decoupling sequence for liquid crystals and solids. J Magn Reson 142:97-101.
30. Andrew ER, Bradbury A, Eades RG. 1959. Removal of dipolar broadening of nuclear magnetic resonance spectra of solids by specimen rotation. Nature (London, United Kingdom) 183:1802-1803.
31. Barich DH, Gorman EM, Zell MT, Munson EJ. 2006. 3-Methylglutaric acid as a 13C solid-state NMR standard. Solid State Nucl Magn Reson 30:125-129.
32. Bielecki A, Burum DP. 1995. Temperature dependence of 207Pb MASspectra of solid lead nitrate. An accurate, sensitive thermometer for variable-temperature MAS. J Magn Reson Ser A 116:215-220.
33. Vyazovkin S, Wight CA. 1997. Isothermal and non-isothermal reaction kinetics in solids: In search of ways toward consensus. J Phys Chem A 101:8279-8284.
34. Vyazovkin S. 2000. Modification of the integral isoconversional method to account for variation in the activation energy. J Comp Chem 22:178-183.
35. Vyazovkin S, Sbirrazzuoli N. 2006. Isoconversional kinetic analysis of thermally stimulated processes in polymers. Macromol Rapid Commun 27:1515-1532.
36. Vyazovkin S. 1997. Evaluation of activation energy of thermally stimulated solid-state reactions under arbitrary variation of temperature. J Comp Chem 18:393-402.
37. Chen LR, Young VG, Jr., Lechuga-Ballesteros D, Grant DJW. 1999. Solid-state behavior of cromolyn sodium hydrates. J Pharm Sci 88:1191-1200.
38. Miroshnyk I, Khriachtchev L, Mirza S, Rantanen J, Heinaemaeki J, Yliruusi J. 2006. Insight into thermally induced phase transformations of erythromycin A dihydrate. Crys Growth Des 6:369-374.
39. Stephenson GA, Groleau EG, Kleemann RL, Xu W, Rigsbee DR. 1998. Formation of isomorphic desolvates: Creating a molecular vacuum. J Pharm Sci 87:536-542.
40. Petit S, Coquerel G. 1996. Mechanism of several solid-solid transformations between dihydrated and anhydrous Copper(II) 8- hydroxyquinolinates. Proposition for a unified model for the dehydration of molecular crystals. Chem Mater 8:2247-2258.
41. Spiess HW, Haeberlen U, Zimmermann H. 1977. Proton multiple-pulse study of a single crystal of trans-diiodoethylene: Example of self-decoupling. J Magn Reson 25:55-66.
42. Harris RK, Olivieri AC. 1992. Quadrupolar effects transferred to spin-1/2 magic-angle spinning spectra of solids. Prog Nucl Magn Reson Spectrosc 24:435-456.
43. Flynn JH, Wall LA. 1966. General treatment of the thermogravimetry of polymers. J Res Natl Bur Std Sec A 70:487-523.
44. Friedman HL. 1964. Kinetics of thermal degradation of char-forming plastics from thermogravimetry-application to a phenolic resin. J Polym Sci No 6: (Pt. C): 183-195.
45. Ozawa T. 1965. A new method of analyzing thermogravimetric data. Bull Chem Soc Jpn 38:1881-1886.
46. Vyazovkin S. 1996. A unified approach to kinetic processing of nonisothermal data. Int J Chem Kinet 28:95-101.
47. Hamaed H, Pawlowski JM, Cooper BFT, Fu R, Eichhorn SH, Schurko RW. 2008. Application of solid-state 35Cl NMR to the structural characterization of hydrochloride pharmaceuticals and their polymorphs. J Am Chem Soc 130:11056-11065.