NOVEL FUROSEMIDE COCRYSTALS AND SELECTION OF HIGH SOLUBILITY DRUG FORMS
679
dilutions from the predetermined standard curves of
the respective compounds. The IDR of the compound
was calculated in the linear region of the dissolu-
tion curve (which is the slope of the curve or amount
of drug dissolved/surface area of the disk) per unit
time. The identity of the undissolved material after
the dissolution experiment was ascertained by PXRD.
The stability of the solid samples after disk compres-
sion and solubility measurements was confirmed by
PXRD.
12. Karami S, Li Y, Hughes DS, Hursthouse MB, Russell AE,
Threlfall TL, Claybourn M, Roberts R. 2006. Further errors
in polymorph identification: Furosemide and finasteride. Acta
Crystallogr B 62:689–691.
13. Babu NJ, Cherukuvada S, Thakuria R, Nangia A. 2010. Con-
formational and synthon polymorphism in furosemide (Lasix).
Cryst Growth Des 10:1979–1989.
14. Ai H, Jones SA, deVilliers MM, Lvov YM. 2003. Nano encapsu-
lation of furosemide microcrystals for controlled drug release.
J Control Release 86:59–68.
15. Matsuda Y, Otsuka M, Onoe M, Tatsumi E. 1992. Amor-
phism and Physicochemical stability of spray-dried frusemide.
J Pharm Pharmacol 44:627–633.
16. Shin SC, Oh IJ, Lee YB, Choi HK, Choi JS. 1998. Enhanced
dissolution of furosemide by coprecipitating or cogrinding with
crospovidone. Int J Pharm 175:17–24.
ACKNOWLEDGMENTS
17. Shin SC, Kim J. 2003. Physicochemical characterization of
solid dispersion of furosemide with TPGS. Int J Pharm
251:79–84.
AN thanks the Department of Science and Technol-
ogy, Government of India (DST) for research fund-
ing (SR/S1/OC-67/2006) and J.C. Bose fellowship (SR/
S2/JCB-06/2009) and Council of Scientific and In-
dustrial Research (CSIR) project (01/2410)/10/EMR-
II). DST (IRPHA) and University Grants Commis-
sion (UGC) (PURSE grant) are thanked for providing
instrumentation and infrastructure facilities at Uni-
versity of Hyderabad (UOH). NRG thanks CSIR, and
KS thanks UGC for a fellowship. Crystalin Research
Pvt. Ltd. (Hyderabad, India) thanks AstraZeneca
Pvt. Ltd. (Bangalore, India) for funding a research
project. We thank Dr. Mike Quayle and Dr. David
Berry (AstraZeneca PLC) for their critical comments
and helpful suggestions. This publication is assigned
AstraZeneca ATP No. 11/1199.
¨
18. Ozdemir N, Ordu S. 1998. Improvement of dissolution proper-
ties of furosemide by complexation with $-cyclodextrin. Drug
Dev Ind Pharm 24:19–25.
19. Kreaz RMA, Abu-Eida EY, Ero˝s I, Kata M. 1999. Freeze dried
complexes of furosemide with $-cyclodextrin derivatives. J Incl
Phenom Macrocycl Chem 34:39–48.
20. Wongmekiat A, Yoshimatsu S, Tozuka Y, Moribe K,
Yamamoto K. 2006. Investigation of drug nanoparticle for-
mation by cogrinding with cyclodextrins: studies for In-
domethacin, Furosemide and Naproxen. J Incl Phenom Macro-
cycl Chem 56:29–32.
21. Yang W, de Villiers MM. 2004. Aqueous solubilization of
furosemide by supramolecular complexation with 4-sulphonic
calix[n]arenes. J Pharm Pharmacol 56:703–708.
22. Zvonar A, Berginc K, Kristl A, Gasˇperlin M. 2010. Microen-
capsulation of self-microemulsifying system: Improving solu-
bility and permeability of furosemide. Int J Pharm 388:151–
158.
23. Latere Dwan’lsa JP, Rouxhet L, Brewster ME, Pre´at
V, Arie¨n A. 2008. Spontaneously self-assembled mi-
celles from poly(ethylene glycol)-b-poly(g-caprolactone-
co-trimethylene carbonate) for drug solubilization. Pharmazie
63:235–240.
REFERENCES
1. Qiu Y, Chen Y, Zhang GGZ., Eds. 2009. Developing solid oral
dosage forms: Pharmaceutical theory and practice, 1st ed.
New York: Academic Press.
24. Shaji J, Jadhav D. 2010. Newer approaches to self emulsifying
drug delivery system. Int J Pharm Pharm Sci 2:37–42.
25. Otsuka M, Onoe M, Matsuda M. 1993. Hygroscopic stability
and dissolution properties of spray-dried solid dispersions of
furosemide with eudragit. J Pharm Sci 82:32–38
26. Brittain HG. 2010. Cocrystal systems of pharmaceutical inter-
est: 2007-2008. Profiles Drug Substances, Excipients Related
Methodology 35:373–390.
27. Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ. 2006.
Pharmaceutical Co-Crystals. J Pharm Sci 95:499–516.
28. Frisˇcˇic´ T, Jones W. 2010. Benefits of cocrystallisation in phar-
maceutical materials science: an update. J Pharm Pharmacol
62:1547–1559.
29. Desiraju GR. 1995. Supramolecular synthons in crystal engi-
neering–A new organic synthesis. Angew Chem, Int Ed Engl
34:2311–2327.
30. Desiraju GR. 2007. Crystal Engineering: A holistic view.
Angew Chem, Int Ed 46: 8342–8356.
31. Bhogala BR, Nangia A. 2003. Cocrystals of 1,3,5-
cyclohexanetricarboxylic acid with 4,4’ bipyridine homologues:
Acid–pyridine hydrogen bonding in neutral and ionic com-
plexes. Cryst Growth Des 3:547–554.
32. Caira MR. 2007. Sulfa drugs as model cocrystal formers. Mol
Pharmaceutics 4:310–316 .
2. Thayer AM. 2010. Finding solutions. Chem Eng News
88:13–18.
3. Amidon GL, Lennernas H, Shah VP, Crison JR. 1995. Theo-
retical basis for a biopharmaceutical drug classification: corre-
lation of in vitro drug product dissolution and in vivo bioavail-
ability. Pharm Res 12:413–420.
4. Dahan A, Miller JM, Amidon GL. 2009. Prediction of solubility
and permeability class membership: Provisional BCS classifi-
cation of world’s top oral drugs. AAPS J 11:740–746.
5. Friedman PA, Berndt WO. 1997. In Modern pharmacology
with clinical applications; Craig CR, Stitzel RE, Eds. 5th ed.
Boston, MA: Little Brown and Company, pp 239–255.
6. Khan MG. 2006. Encyclopedia of heart diseases. 15th ed.New
York: Elsevier, pp 486.
7. Blagden N, de Matas M, Gavan PT, York P. 2007. Crystal
engineering of active pharmaceutical ingredients to improve
solubility and dissolution rates. Adv Drug Del Rev 59:617–630.
8. Shan N, Zaworotko MJ. 2008. The role of cocrystals in phar-
maceutical science. Drug Discov Today 13:440–446.
9. Doherty C, York P. 1988. Furosemide crystal forms: Solid state
and physicochemical analyses. Int J Pharm 47:141–155.
10. Matsuda Y, Tatsumi E. 1990. Physicochemical characteriza-
tion of furosemide modifications. Int J Pharm 60:11–26.
11. Ge M, Liu G, Ma S, Wang W. 2009. Polymorphic forms of
furosemide characterized by THz time domain spectroscopy.
Bull Korean Chem Soc 30:2265–2268.
33. Ishida T, In Y, Doi M, Inoue M, Yanagisawa I. 1989.
Structural study of Histamine H2–receptor antagonists. Five
DOI 10.1002/jps
JOURNAL OF PHARMACEUTICAL SCIENCES, VOL. 101, NO. 2, FEBRUARY 2012