Solid-state characterization of novel active pharmaceutical ingredients: Cocrystal of a salbutamol hemiadipate salt with adipic acid (2:1:1) and salbutamol hemisuccinate salt

Journal of Pharmaceutical Sciences

Volumn 100, Issue 8, 2011, Pages 3268-3283

  Paluch, Krzysztof J ^a   Tajber, Lidia ^a   Elcoate, Curtis J ^b   Corrigan, Owen I ^a   Lawrence, Simon E ^b   Healy, Anne Marie ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

Cocrystals; Crystal structure; Desolvation; Dissolution rate; Solubility; Solvate; Thermal analysis; Water sorption; X ray powder diffraction

Indexed keywords

ADIPIC ACID; SALBUTAMOL; SALBUTAMOL HEMIADIPATE; SALBUTAMOL HEMISUCCINATE; SALBUTAMOL HEMISUCCINATE TETRAMETHANOLATE; SALBUTAMOL SULFATE; SUCCINIC ACID; SULFATE; UNCLASSIFIED DRUG; VENTMAX; VOLMAX CR;

ARTICLE; CRYSTAL; CRYSTALLIZATION; DISSOLUTION; EVAPORATION; HUMIDITY; HYDRATION; SOLID STATE; SOLUBILITY; STOICHIOMETRY;

EID: 79958831526     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22569     Document Type: Article

References (44)

1. BMJ Publishing. British National Formulary: Current edition. Accessed October 29, 2010, at:http://bnf.org/bnf/index.htm.
2. Jashnani RN, Byron PR, Dalby RN. 1993. Preparation, characterization, and dissolution kinetics of two novel albuterol salts. J Pharm Sci 82(6):613-616.
3. Beale JP, Grainger CT. 1972. DL-N-t-Butyl-2(4-hydroxy-3-hydroxymethylphenyl)2-hydroxyethylamine, (salbutamol, Ah. 3365), C13H21NO3. Cryst Struct Commun 67(1):71-74.
4. 4]. Acta Crystallogr B34:1203-1208.
5. Council of Europe. 2007. European Pharmacopoeia. 6th ed. 5.4. Strasbourg, France: Council of Europe.
6. Vyse T, Cochrane GM. 1989. Controlled release salbutamol tablets versus sustained release theophylline tablets in the control of reversible obstructive airways disease. J Int Med Res 17(1):93-98.
7. Murthy SN, Shobharani HR. 2004. Clinical pharmacokinetic and pharmacodynamic evaluation of transdermal drug delivery systems of salbutamol sulfate. Int J Pharm 287:47-53.
8. Micromedex® Healthcare Series [intranet database]. Version 5.1. Greenwood Village, Colorado: Thomson Reuters (Healthcare) Inc.
9. British Pharmacopeia. 2010. ISBN 9780113228287. London, England: The Stationery Office.
10. O'Connor KM, Corrigan OI. 2001. Preparation and characterisation of a range of diclofenac salts. Int J Pharm 226:163-179.
11. Stahl PH, Wermuth CG. 2008. Handbook of Pharmaceutical salts properties, selection, and use. ISBN 3-906390-26-8. Weinhem, Germany, Wiley-VCH.
12. Jones PH, Rowley E, Weiss AL, Bishop DL, Chun AH. 1969. Insoluble erythromycin salts. J Pharm Sci 58 (3):337-339.
13. Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD. 2002. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 45:2615-2623.
14. 15N NMR spectroscopy. J Am Chem Soc 128:8199-8210.
15. Imboden R, Imanidis G. 1999. Effect of the amphoteric properties of salbutamol on its release rate through a propylene control membrane. Eur J Pharm Biopharm 47:161-167.
16. FDA. Database of Select Committee on GRAS Substances (SCOGS) Reviews, Succinic acid. Accessed December 17, 2010, at:
17. FDA. Database of Select Committee on GRAS Substances (SCOGS) Reviews, Adipic acid. Accessed December 17, 2010, at:
18. Sheldrick GM. 2008. A short history of SHELX. Acta Crystallogr A 64:112-122.
19. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA. 2008. J Appl Crystallogr 41:466-470.
20. Tajber L, Corrigan DO, Corrigan OI, Healy AM. 2009. Spray drying of budesonide, formoterol fumarate, and their composites. I. Physicochemical characterisation. Int J Pharm 367:79-85.
21. Tajber L, Corrigan OI, Healy AM. 2005. Physicochemical evaluation of PVP-thiazide diuretic interactions in co-spray-dried composites-Analysis of glass transition composition relationships. Eur J Pharm Sci 24:553-563.
22. Healy AM, McDonald BF, Tajber L, Corrigan OI. 2008. Characterisation of excipient-free nanoporous microparticles (NPMPs) of bendroflumethiazide. Eur J Pharm Biopharm 69:1182-1186.
23. Paluch KJ, Tajber L, McCabe T, O'Brien JE, Corrigan OI, Healy AM. 2010. Preparation and solid state characterisation of chlorothiazide sodium intermolecular self assembly suprastructure. Eur J Pharm Sci 41:603-611.
24. Fadda HM, Sousa T, Carlsson AS, Abrahamsson B, Williams JG, Kumar D, Basit AW. 2010. Drug solubility in luminal fluids from different regions of the small and large intestine of humans. Mol Pharmacol 7(5):1527-1532.
25. Thoma K, Ziegler I. 1998. Simultaneous quantification of released succinic acid and a weakly basic drug compound in dissolution media. Eur J Pharm Biopharm 46:183-190.
26. Kordis-Krapez M, Abram V, Kac M, Ferjancic S. 2001. Determination of organic acids in white wines by RP-HPLC. Food Technol Biotechnol 39:93-99.
27. Healy AM, Corrigan OI. 1996. The influence of excipient particle size, solubility and acid strength on the dissolution of an acidic drug from two-component compacts. Int J Pharm 143(2):211-221.
28. Nocent M, Bertocchi L, Espitalier F, Baron M, Couarraze G. 2001. Definition of a solvent system for spherical crystallization of salbutamol sulfate by quasi-emulsion solvent diffusion (QESD) method. J Pharm Sci 90(10):1620-7.
29. Gad E, Mahmoud A, Khairou KS. 2008. QSPR for HLB of nonionic surfactants based on polyoxyethylene group. J Dispersion Sci Technol 29(7):940-947.
30. Haynes DA, Jones W, Motherwell WDS. 2005. Occurrence of pharmaceutically acceptable anions and cations in the Cambridge structural database. J Pharm Sci 94:2111-2120.
31. Petrusevski G, Naumov P, Jovanovski G, Bogoeva-Gaceva G, Weng Ng S. 2008. Solid-state forms of sodium valproate, active component of the anticonvulsant drug epilim. Chem Med Chem 3:1377-1386.
32. Bailey RD, Walsh MW, Bradner S, Fleischman L, Morales A, Moulton B, Rodríguez-Hornedo N, Zaworotko MJ. 2003. Crystal engineering of the composition of pharmaceutical phases. Chem Commun 2:186-187.
33. McNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet MS, Mannion R, O'Donnell E, Park A. 2006. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharm Res 23(8):1888-1897.
34. Variankaval N, Wenslow R, Murry J, Hartman R, Helmy R, Kwong E, Clas SD, Dalton C, Santos I. 2006. Preparation and solid-state characterization of nonstoichiometric cocrystals of a phosphodiesterase- IV inhibitor and l-tartaric acid. Cryst Growth Des 6:690-700.
35. Zegarac M, Mestrovic E, Dumbovic A, Devcic M, Tudja P. 2007. Pharmaceutically acceptable cocrystalline forms of sildenafil. WO/2007/080362.
36. Shan N, Zaworotko MJ. 2008. The role of cocrystals in pharmaceutical Science. Drug Discovery Today 13(9-10):440-446.
37. Dova E, Mazurek JM, Anker J. 2008. Tenofovir disoproxil hemi-fumaric acid co-crystal WO/2008/143500.
38. Cheney ML, Shan N, Healey ER, Mazen H, Wojtas Ł, Zaworotko MJ, Sava V, Song S, Sanchez-Ramos JR. 2010. Effects of crystal form on solubility and pharmacokinetics: A crystal engineering case study of lamotrigine. Cryst Growth Des 10(1):394-405.
39. Harrison WTA, Yathirajan HS, Bindya S, Anilkumar HG Devaraju, 2007. Escitalopram oxalate: Co-existence of oxalate dianions and oxalic acid molecules in the same crystal. Acta Crystallogr C63:129-131.
40. Regla I, Reyes A, Körber C, Demare P, Estrada O, Juaristi E. 1997. Novel applications of raney nickel/isopropanol: Efficient system for the reduction of organic compounds. Synth Commun 27(5):817-823.
41. Larhrib H, Martin GP, Marriott C, Prime D. 2003. The influence of carrier and drug morphology on drug delivery from dry powder formulations. Int J Pharm 257:283-296.
42. Sreenivas RL, Bethune SJ, Kampf JW, Rodriguez Hornedo N. 2009. Cocrystals and salts of gabapentin: pH dependent cocrystal stability and solubility. Cryst Growth Des 9(1):378-385.
43. Bethune SJ, Huang N, Jayasankar A, Rodriguez-Hornedo N. 2009. Understanding and predicting the effect of cocrystal components and pH on cocrystal solubility. Cryst Growth Des 9(9):3976-3988.
44. Yazan Y, Demirel M, Güler E. 1995. Preparation and in vitro dissolution of salbutamol sulfate microcapsules and tabletted microcapsules. J Microencapsul 12:601-607.