Crystal polymorphism in a carbamazepine derivative: Oxcarbazepine

Journal of Pharmaceutical Sciences

Volumn 99, Issue 2, 2010, Pages 794-803

  Lutker, Katie M ^a   Matzger, Adam J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Calorimetry (DSC); Crystal structure; Polymorphism; Raman spectroscopy; X ray diffractometry

Indexed keywords

OXCARBAZEPINE;

ARTICLE; CHEMICAL MODIFICATION; CONFORMATION; CRYSTAL STRUCTURE; DRUG STRUCTURE; LOW TEMPERATURE; MICROSCOPY; PREDICTION; RAMAN SPECTROMETRY; THEORETICAL MODEL; THERMOMICROSCOPY; X RAY POWDER DIFFRACTION;

EID: 74049161627     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21873     Document Type: Article

References (19)

1. Brittain HG. 1999. Polymorphism in pharmaceutical solids. 1st editon. New York: Marcel Dekker.
2. Gavezzotti A, Filippini G. 1995. Polymorphic forms of organic-crystals at room conditions-Thermodynamic and structural implications. J Am Chem Soc 117:12299-12305.
3. Yu L, Reutzel-Edens SM, Mitchell CA. 2000. Crystallization and polymorphism of conformationally flexible molecules: Problems, patterns, and strategies. Org Process Res Dev 4:396-402.
4. Lang MD, Grzesiak AL, Matzger AJ. 2002. The use of polymer heteronuclei for crystalline polymorph selection. J Am Chem Soc 124:14834-114835.
5. Price CP, Grzesiak AL, Matzger AJ. 2005. Crystalline polymorph selection and discovery with polymer heteronuclei. J Am Chem Soc 127:5512-5517.
6. Grzesiak AL, Lang MD, Kim K, Matzger AJ. 2003. Comparison of the four anhydrous polymorphs of carbamazepine and the crystal structure of form I. J Pharm Sci 92:2260-2271.
7. Bandoli G, Nicolini M, Ongaro A, Volpe G, Rubello A. 1992. X-ray crystallographic characterization of 10,11-dihydro-5H-dibenz[b,f]azepine-5- carboxamide. J Crystallogr Spectrosc Res 22:177-183.
8. Harrison WTA, Yathirajan HS, Anilkumar HG. 2006. An orthorhombic polymorph of 10,11-dihydro-carbamazepine. Acta Crystallogr C 62:240-242.
9. Leech CK, Florence AJ, Shankland K, Shankland N, Johnston A. 2007. 10,11-dihydrocarbamazepine (form III). Acta Crystallogr E 63:675-677.
10. Aronhime J, Dolitzky B-H, Berkovich Y, Garth N. Crystal forms of oxcarbazepine and processes for their preparation. US7183272 (published on February 27, 2007).
11. Venkataraman S, RajuNS, Purandhar K, Reddy LA, Kondaiah GCM. Crystalline form of oxcarbazepine. US20060166968 (published on July 15, 2005).
12. Hempel A, Camerman N, Camerman A,Mastropaolo D. 2005. Oxcarbazepine: Structure and anticonvulsant activity. Acta Crystallogr E 61:1313-1315.
13. Cabeza AJC, Day GM, Motherwell WDS, Jones W. 2007. Importance of molecular shape for the overall stability of hydrogen bond motifs in the crystal structures of various carbamazepine-type drug molecules. Cryst Growth Des 7:100-107.
14. Lutker KM, Tolstyka ZP, Matzger AJ. 2008. Investigation of a priveleged polymorphic motif: A dimeric ROY derivative. Cryst Growth Des 8:136-139.
15. Burla MC, Caliandro R, Camalli M, Carrozzini B, Cascarano GL, De Caro L, Giacovazzo C, Polidori G, Spagna R. 2005. SIR2004: An improved tool for crystal structure determination and refinement. J Appl Crystallogr 38:381-388.
16. 2000-2005. CrystalStructure 3.7.0 ed. ed., The Woodlands, TX 77381: Rigaku and Rigaku/MSC. p Crystal Structure Analysis Package.
17. Sheldrick GM. 1997. SHELXS97 and SHELXL97. Germany: University of Gottingen.
18. Bellucci G, Cinzia C, Marchetti F. 1995. Conformational process and symmetry in N-substituted 10,11-dihydro-5H-dibenz[b,f]azepine and 1a,10b-dihydro-6H-dibenzo[b,f]oxireno[d]azepine Derivatives. Gazz Chim Ital 125:341-346.
19. Lisgarten JN, Palmer RA, Saldanha JW. 1989. The structure of 10,11-dihydro-10-hydroxy-5h-dibenz[B,F] azepine-5-carboxamide, an anticonvulsant drug molecule. Acta Crystallogr C 45:656-658.