Advertisement

Photoluminescence of Pharmaceutical Materials in the Solid State. 4. Fluorescence Studies of Various Solvated and Desolvated Solvatomorphs of Erythromycin A

  • Harry G. Brittain
Part of the Reviews in Fluorescence book series (RFLU, volume 2007)

Abstract

The hydrate, methanolate, ethanolate, and isopropanolate solvatomorphs of erythromycin A have been prepared and characterized as to their crystallographic and solvent content characteristics. Even though erythromycin A does not exhibit fluorescence when in a dissolved state, in the solid state the solvated materials were found to be mildly fluorescent. Differences in fluorescence intensity were noted among the solvatomorphs, which could be roughly correlated with the degree of crystallinity of the materials. Desolvation of the dihydrate phase (known to yield an isomorphic desolvate) led to only minor changes in the excitation and emission spectra, but desolvation of the alchoholate solvatomorphs (known to yield largely amorphous products) caused large decreases in the intensities of the excitation and emission spectra. Since the fluorescence properties of organic solids are critically dependent on the details of the crystal structure and the delocalization of excitation energy, the loss of crystal structure appears to suppress the degree of energy transfer and this in turn affects the fluorescence intensities.

Keywords

Ethanolate Product Excitation Spectrum Emission Band Wavelength Maximum Induce Weight Loss 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Allen PV, Rahn PD, Sarapu AC, Vanderwielen AJ (1978). “Physical Characterization of Erythromycin: Anhydrate, Monohydrate, and Dihydrate Crystalline Solids.” J. Pharm. Sci., 67, 1087–1093.CrossRefPubMedGoogle Scholar
  2. 2.
    Bauer J, Quick J, Oheim R. (1985). “Alternate Interpretation of the Role of Water in the Erythromycin Structure.” J. Pharm. Sci., 74, 899–900.CrossRefGoogle Scholar
  3. 3.
    Bernstein J (2002). “Analytical Techniques for Studying and Characterizing Polymorphs.” in Polymorphism in Molecular Crystals, Clarendon Press, London, pp. 94–150.Google Scholar
  4. 4.
    Brittain HG (1997). “Spectral Methods for the Characterization of Polymorphs and Solvates.” J. Pharm. Sci., 86, 405–412.CrossRefPubMedGoogle Scholar
  5. 5.
    Brittain HG (1999). “Methods for the Characterization of Polymorphs and Solvates.” in Polymorphism in Pharmaceutical Solids, Brittain HG ed.;: Marcel Dekker, New York, pp. 227–278.Google Scholar
  6. 6.
    Brittain HG, Elder BJ, Isbester PK, Salerno AH (2005a). “Solid-State Fluorescence Studies of Some Polymorphs of Diflunisal.” Pharm. Res., 22, 999–1006.CrossRefPubMedGoogle Scholar
  7. 7.
    Brittain HG (2005b). “Solid-State Fluorescence of the Trihydrate Phases of Ampicillin and Amoxicillin”, AAPS PharmSciTech, 6(3), article 55.Google Scholar
  8. 8.
    Brittain HG (2006). “Luminescence Spectroscopy.” in Spectroscopy of Pharmaceutical Solids, Brittain HG ed., Taylor & Francis, New York, pp. 151–204.CrossRefGoogle Scholar
  9. 9.
    Craig DP, Walmsley SH (1968). Excitons in Molecular Crystals. W.A. Benjamin, New York.Google Scholar
  10. 10.
    Davydov AS (1962). Theory of Molecular Excitons. McGraw-Hill, New York.Google Scholar
  11. 11.
    Fukumori Y, Fukuda T, Yamamoto Y, Shigitani Y, Hanyu Y, Takeuchi Y, Sato N (1983). “Physical Characterization of Erythromycin Dihydrate, Anhydrate and Amorphous Solid and their Dissolution Properties.” Chem. Pharm. Bull., 31, 4029–4039.Google Scholar
  12. 12.
    Koch WL (1979). “Erythromycin”, in Analytical Profiles of Drug Substances, Florey K, ed., Academic Press, New York, pp. 159–177.Google Scholar
  13. 13.
    Laine E, Kahela P, Rajala R, Heikkila T, Saarnivaara K, Piippo I (1987). “Crystal Forms and Bioavailability of Erythromycin.” Int. J. Pharm., 38, 33–38.CrossRefGoogle Scholar
  14. 14.
    Merck Index (2001). Merck & Co., Inc., Whitehouse Station, NJ, pp. 654–655.Google Scholar
  15. 15.
    Miroshnyk I, Khriachtchev L, Mirza S, Rantanen J, Heinamaki J, Yliruusi J (2006). “Insight into Thermally Induced Phase Transformations of Erythromycin A Dihydrate.” Cryst. Growth Design, 6, 369–374.CrossRefGoogle Scholar
  16. 16.
    Mirza S, Miroshnyk I, Heinamaki J, Christiansen L, Karjalainen M, Yliruusi J (2003). “Influence of Solvents on the Variety of Crystalline Forms of Erythromycin”. AAPS PharmSci, 5(2), article 12.Google Scholar
  17. 17.
    Murthy KS, Turner NA, Nesbitt RU, Fawzi MB (1986). “Characterization of Commercial Lots of Erythromycin Base.” Drug Dev. Indust. Pharm., 12, 665–690.CrossRefGoogle Scholar
  18. 18.
    Sarisuta N, Kumpugdee M, Muller BW, Puttipipatkhachorn S (1999). “Physico-Chemical Characterization of Interactions Between Erythromycin and Various Film Polymers.” Int. J. Pharm., 186, 109–118.CrossRefPubMedGoogle Scholar
  19. 19.
    Stephenson GA, Stowell JG, Pascal HT, Pfeiffer RR, Byrn SR (1997). “Solid-State Investigations of Erythromycin A Dihydrate: Structure, NMR Spectroscopy, and Hygroscopicity.” J. Pharm. Sci., 86, 1239–1244.CrossRefPubMedGoogle Scholar
  20. 20.
    Stephenson GA, Groleau EG, Kleemann RL, Xu W, Rigsbee DR (1998). “Formation of Isomorphic Desolvates: Creating a Molecular Vacuum.” J. Pharm. Sci., 87, 536–542.CrossRefPubMedGoogle Scholar
  21. 21.
    Threlfall TL (1995). “Analysis of Organic Polymorphs – A Review.” Analyst, 120, 2435–2460.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Center for Pharmaceutical PhysicsMilfordUSA

Personalised recommendations