Polymorphism of NCX4016, an NO-Releasing Derivative of Acetylsalicylic Acid

Journal of Pharmaceutical Sciences

Volumn 93, Issue 3, 2004, Pages 521-531

  Foppoli, A ^a   Sangalli, M E ^a   Maroni, A ^a   Gazzaniga, A ^a   Caira, M R ^b   Giordano, F ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

^c UNIVERSITY OF PARMA   (Italy)

Author keywords

Crystal structure; Intrinsic dissolution rate; Melting data method; Nitrooxyaspirin derivative; Polymorphism; Thermodynamics

Indexed keywords

ACETYLSALICYLIC ACID; ACETYLSALICYLIC ACID 3 (NITROXYMETHYL)PHENYL ESTER; ACETYLSALICYLIC ACID DERIVATIVE; NITROUS OXIDE; SOLVENT;

ANALGESIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CALCULATION; CRYSTAL STRUCTURE; DRUG DETERMINATION; DRUG SAFETY; DRUG SCREENING; DRUG STRUCTURE; GASTROINTESTINAL TRACT; INFRARED SPECTROSCOPY; MELTING POINT; SCANNING ELECTRON MICROSCOPY; THERMAL ANALYSIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY; X RAY POWDER DIFFRACTION;

EID: 1542410400     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.10547     Document Type: Article

References (19)

1. Al-Swayeh OA, Clifford RH, Del Soldato P, Moore PK. 2000. A comparison of the anti-inflammatory and anti-nociceptive activity of nitroaspirin and aspirin. Br J Pharmacol 129(2):343-350.
2. Wallace JL, Muscara MN, McKnight W, Dicay M, Del Soldato P, Cirino G. 1999. In vivo antithrombotic effects of a nitric oxide-releasing aspirin derivative, NCX-4016. Thromb Res 93(1): 43-50.
3. Rossoni G, Berti M, De Gennaro Colonna V, Bernareggi M, Del Soldato P, Berti F. 2000. Myocardial protection by the nitroderivative of aspirin, NCX4016: In vitro and in vivo experiments on rabbit. Ital Heart J 1(2):146-155.
4. Napoli C, Cirino G, Del Soldato P, Sorrentino R, Sica V, Condorelli M, Pinto A, Ignarro LJ. 2001. Effects of nitric oxide-releasing aspirin versus aspirin on restenosis in hypercholesterolemic mice. Proc Natl Acad Sci 98(5):2860-2864.
5. Bak AW, McKnight W, Li P, Del Soldato P, Calignano A, Cirino G, Wallace JL. 1998. Cyclooxygenase-independent chemoprevention with an aspirin derivative in a rat model of colonic adenocarcinoma. Life Sci 62(33):367-373.
6. Fiorucci S, Mencarelli A, Mannucci R, Distrutti E, Morelli A, del Soldato P, Moncada S. 2002. NCX4016, a nitric oxide-releasing aspirin, protects endothelial cells against apoptosis by modulating mitochondrial function. FASEB J 16(12):1645-1647.
7. Takeuchi K, Ukawa H, Konaka A, Kitamura M, Sugawa Y. 1998. Effect of nitric oxide-releasing aspirin derivative on gastric functional and ulcerogenic responses in rat: Comparison with plain aspirin. J Pharmacol Exp Ther 286(1):115-121.
8. Fiorucci S, Santucci L, Mencarelli A, Del Soldato P, Morelli A. 2002. Gastrointestinal safety of a NO-releasing aspirin derivative (NCX4016) in humans: a double blind placebo controlled endoscopic study. Gastroenterology Suppl 122(151).
9. Grant DJW. 1998. Theory and origin of polymorphism. In: Brittain HG, editor. Polymorphism in pharmaceutical solids. New York: Marcel Dekker, pp 1-33.
10. Otwinowski Z, Minor W. 1997. Processing of X-ray diffraction data collected in oscillation mode. In: Carter CW, Sweet RM, editors. Methods in enzymology. New York: Academic Press, pp 307-326.
11. Sheldrick GM. 1985. SHELXS86. In: Sheldrick GM, Kruger GM, Goddard R, editors. Crystallographic computing 3. Oxford: Oxford University Press, pp 175-189.
12. Sheldrick GM. 1997. SHELXL97 program for the refinement of crystal structures. Germany: University of Göttingen.
13. Spek AL. 1990. PLATON, an integrated tool for the analysis of the results of a single crystal structure determination. Acta Crystallogr A46:C34.
14. Zsolnai L, Pritzkow H. 1994. ZORTEP: ORTEP program for personal computer. Germany: University of Heidelberg.
15. Yvon K, Jeitschko W, Parthe E. 1977. LAZY PULVERIX, a computer program for calculating X-ray and neutron diffraction powder patterns. J Appl Crystallogr 10:73-74.
16. Burger A, Ramberger R. 1979. On the polymorphism of pharmaceuticals and other organic molecular crystals. I. Theory of thermodynamic rules. Mikrochim Acta [Wien] 11:259-271.
17. Kim Y, Machida K, Taga T, Osaki K. 1985. Structure redetermination and packing analysis of aspirin crystal. Chem Pharm Bull 33(7):2641-2647.
18. Yu L. 1995. Inferring thermodynamic stability relationship of polymorphs from melting data. J Pharm Sci 84(8):966-974.
19. Aguiar AJ, Zelmer JE. 1969. Dissolution behavior of polymorphs of chloramphenicol palmitate and mefenamic acid. J Pharm Sci 58(8): 983-987.