Characterization of nicergoline polymorphs crystallized in several organic solvents

Journal of Pharmaceutical Sciences

Volumn 100, Issue 7, 2011, Pages 2610-2622

  Malaj, Ledjan ^a,b   Censi, Roberta ^a,c   Capsoni, Doretta ^d   Pellegrino, Luca ^e   Bini, Marcella ^d   Ferrari, Stefania ^d   Gobetto, Roberto ^e   Massarotti, Vincenzo ^d   Martino, Piera Di ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF TIRANA   (Albania)

^c UTRECHT UNIVERSITY   (Netherlands)

^d UNIVERSITY OF PAVIA   (Italy)

^e UNIVERSITY OF TURIN   (Italy)

Author keywords

Dissolution; Monotropy; Nicergoline; Polymorphism; Solid state NMR; Solubility; Thermal analysis

Indexed keywords

CHLORIDE; NICERGOLINE; ORGANIC SOLVENT;

ARTICLE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG ANALYSIS; DRUG DELIVERY SYSTEM; DRUG SOLUBILITY; DRUG STRUCTURE; PARTICLE SIZE; PREFORMULATION; ROOM TEMPERATURE; SOLID STATE; X RAY POWDER DIFFRACTION;

EID: 79955636924     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22477     Document Type: Article

References (26)

1. Amidon GL, Lennernäs H, Shah VP, Crison JR. 1995. A theoretical basis for a biopharmaceutical drug classification: The correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res 12:413-420.
2. Leuner C, Dressman J. 2000. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 50:47-60.
3. Lipinski C. 2001. Poor aqueous solubility-An industry wide problem in drug delivery. Am Pharm Rev 5:82-85.
4. Al-Saieq SS, Riley GS. 1982. Polymorphism in sulphonylurea hypoglycaemic agents: II. Chlorpropamide. Pharm Acta Helv 57:8-11.
5. Haleblian J, McCrone W. 1969. Pharmaceutical applications of polymorphism. J Pharm Sci 58:911-929.
6. Hörter D, Dressman JB. 1997. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv Drug Del Rev 25:3-14.
7. Khankari RK, Grant DJW. 1995. Pharmaceutical hydrates. Thermochim Acta 248:61-79.
8. Chawla G, Bansal AK. 2007. A comparative assessment of solubility advantage from glassy and crystalline forms of a water-insoluble drug. Eur J Pharm Sci 32:45-57.
9. Woodcock BG, Acerbi D, Merz PG, Rietbrock S, Rietbrock N. 1993. Supermolecular inclusion of piroxicam with β-cyclodextrin: Pharmacokinetic properties in man. Eur J Rheumatol Inflamm 12:12-28.
10. Miyayi T, Inoue Y, Acarturk F, Imai T, Otagiri M, Uekama K. 1992. Improvement of oral bioavailability of fenbufen by cyclodextrin complexations. Acta Pharm Nord 4:17-22.
11. Verheven S, Blaton N, Kinget R, Van Den Mooter G. 2002. Mechanism of increased dissolution of diazepam and temazepam from polyethylene glycol 6000 solid dispersions. Int J Pharm 249:45-58.
12. Heitz C, Descombes JJ, Miller RC, Stoclet JC. 1986. α-Adrenoceptor antagonistic and calcium antagonistic effects of nicergoline in the rat isolated aorta. Eur J Pharmacol 123:279-285.
13. Brossi A. 1990. The alkaloids. Chemistry and pharmacology. Vol. 38. San Diego, California: Academic Press Inc., p 142.
14. Venn RD. 1980. Review of clinical studies with ergots in gerontology. In: Ergot compounds and brain function; Goldstein M, Liberman A, Calne DB, Thorner MO, Eds. New York: Raven Press, pp 363-377.
15. Goo D, Palosi E, Szporny L. 1988. Comparison of the effects of vinpocetine, vincamine, and nicergoline on the normal and hypoxia-damaged learning process in spontaneously hypertensive rats. Drug Dev Res 15:75-85.
16. Pastoris O, Vercesi L, Allorio F, Dossena M. 1988. Effect of hypoxia, aging and pharmacological treatment on muscular metabolites and enzyme activities. Farmaco Sci 43:627-642.
17. Triulzi E, Devizzi S, Margonato A. 1981. Use of nicergoline in acute myocardial infarction with diastolic hypertension. Farmaco Prat 36:449-455.
18. Hušák M, Had J, Kratochvíl B, Cvak L, Stuchlík J, Jegorov A. 1994. X-ray absolute structure of nicergoline (form I). Quantitative analysis of nicergoline phase mixture: FormI/form II. Coll Czech Chem Commun 59:1624-1636.
19. Husàk M, Kratochvil B, Ondraček J, Maixner J, Jerolov A, Stuchlik J. 1994. The crystal and absolute molecular structure od "low melting" nicergoline (form II). Z Kristallogr 209:260-262.
20. Foresti E, Sabatino P, Riva di Sanseverino L, Fusco R, Tosi C, Tonani R. 1988. Structure and molecular orbital study of ergoline derivatives. 1-(6-Methyl-8β-ergolinylmethyl)imidazolidine-2, 4-dione (I) and 2-(10-methoxy-1, 6-dimethyl-8β-ergolinyl)ethyl 3, 5-dimethyl-1H-2-pyrrolecarboxylate toluene hemisolvate (II) and comparison with nicergoline (III). Acta Cryst B44:307-315.
21. Bruker AXS. 2005. TOPAS V3.0: General profile and structural analysis software for powder diffraction data. User Manual Bruker AXS, Karlsruhe, Germany.
22. Banakar UV. 1992. Pharmaceutical dissolution testing. In: Swarbrick J. Ed., New York: Marcel Dekker, pp 55-105.
23. Burger A, Ramberger R. 1979. On the polymorphism of pharmaceuticals and other molecular crystals. I. Theory of thermodynamic rules. Mikrochim Acta 2:259-271.
24. Li H, Kiang Y-H, Jona J. 2009. Multiple approaches to pharmaceutical polymorphism investigation-A case study. Eur J Pharm Sci 38:426-432.
25. Yang X, Wang X, Ching CB. 2008. Solubility of form α and form γ of glycine in aqueous solutions. J Chem Eng Data 53:1133-1137.
26. Nordstrom FL, Rasmuson AC. 2006. Polymorphism and thermodynamics of m-hydroxybenzoic acid. Eur J Pharm Sci 28:377-384.