A new insight into solid-state conformation of macrolide antibiotics

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 1, 2008, Pages 232-239

  Miroshnyk, Inna ^a   Mirza, Sabiruddin ^a   Zorky, Petr M ^b   Heinämäki, Jyrki ^a   Yli Kauhaluoma, Jari ^a   Yliruusi, Jouko ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Conformation analysis; Erythromycin derivatives; In vivo behavior; Interaction energy; Macrolide antibiotics; Non covalent interactions

Indexed keywords

BERYTHROMYCIN; CLADINOSE; CLARITHROMYCIN; DEXTRO DESOSAMINE; ERYTHROMYCIN; ERYTHRONOLIDE; MACROCYCLIC COMPOUND; MACROLIDE; MONOSACCHARIDE; ROXITHROMYCIN; UNCLASSIFIED DRUG;

AREA UNDER THE CURVE; ARTICLE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CONFORMATION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG STRUCTURE; HUMAN; MOLECULAR INTERACTION; QUANTITATIVE ANALYSIS; SINGLE DRUG DOSE; SOLID STATE;

ANTI-BACTERIAL AGENTS; CLARITHROMYCIN; ERYTHROMYCIN; MACROLIDES; MOLECULAR CONFORMATION; MONOSACCHARIDES; ROXITHROMYCIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 38049041426     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.09.044     Document Type: Article

References (48)

1. Kuntz I. Science 257 (1992) 1078-1082
2. Taskinen J., and Yliruusi J. Adv. Drug Deliv. Rev. 55 (2003) 1163-1183
3. Hodgson J. Nat. Biotechnol. 19 (2001) 722-726
4. Wenlock M.C., Austin R.P., Barton P., Davis A.M., and Leeson P.D. J. Med. Chem. 46 (2003) 1250-1256
5. Prentis R.A., Lis Y., and Walker S.R. Br. J. Clin. Pharmacol. 25 (1988) 387-396
6. Schlünzen F., Zarivach R., Harms J., Bashan A., Tocilj A., Albrecht R., Yonath A., and Franceschl F. Nature 413 (2001) 814-821
7. Bertho G., Gharbi-Benarous J., Delaforge M., and Girault J.P. Bioorg. Med. Chem. 6 (1998) 209-221
8. van de. van de Waterbeemd H., Smith D.A., Beaumont K., and Walker D.K. J. Med. Chem. 44 (2001) 1313-1333
9. Rubinstein E. Int. J. Antimicrob. Agents 18 (2001) S71-S76
10. Steiner J.P., Connolly M.A., Valentine H.L., Hamilton G.S., Dawson T.M., Hester L., and Snyder S.H. Nat. Med. 3 (1997) 421-428
11. Peeters T.L. Gastroenterology 105 (1993) 1886-1899
12. Ianaro A., Ialenti A., Maffia P., Sautebin L., Rombola L., Carnuccio R., Iuvone T., D'Acquisto F., and Di Rosa M. J. Pharmacol. Exp. Ther. 292 (2000) 156-163
13. Bryskier A., Agouridas C., and Chantot J.F. Exp. Opin. Invest. Drugs 3 (1994) 405-410
14. Yatsunami J., Fukuno Y., Nagata M., Tsuruta N., Aoki S., Tominaga M., Kawashima M., Taniguchi S., and Hayashi S. Cancer Lett. 147 (1999) 17-24
15. Hamada K., Kita E., Sawaki M., Mikasa K., and Narita N. Chemotherapy 41 (1995) 59-69
16. Allevi P., Longo A., and Anastasia M. Bioorg. Med. Chem. 7 (1999) 2749-2752
17. Gunnesa S., and Undheim K. Bioorg. Med. Chem. 15 (2007) 119-129
18. Desiraju G.R. Nature 412 (2001) 397-400
19. Kobayashi Y., Ito S., Itai S., and Yamamoto K. Int. J. Pharm. 193 (2000) 137-146
20. Docherty R., and Meenan P. In: Myerson A.S. (Ed). Molecular Modelling Applications in Crystallization (1999), Cambridge University Press, New York 106-130
21. Stephenson G.A., Stowell J.G., Toma P.H., Pfeiffer R.R., and Byrn S.R. J. Pharm. Sci. 86 (1997) 1239-1244
22. Bachet B., Brassy C., and Mornon J.-P. Acta Crystallogr. C44 (1988) 112-116
23. Awan A., Brennan R.J., Regan A.C., and Barber J. J. Chem. Soc., Perkin Trans. 2 (2000) 1645-1652
24. Bertho G., Ladam P., Gharbi-Benarous J., Delaforge M., and Girault J.-P. Int. J. Biol. Macromol. 22 (1998) 103-127
25. Everett J.R., and Tyler J.W. J. Chem. Soc., Perkin Trans. 2 3 (1988) 325-337
26. Zorkii P.M., and Zefirov Y.V. Russ. Chem. Rev. 64 (1995) 415-428
27. Novak P., Tomišić Z.B., Tepeš P., Lazarevski G., Plavec J., and Turkalj G. Org. Biomol. Chem. 3 (2005) 39-47
28. Amsden G.W. Int. J. Antimicrob. Agents 18 (2001) S11-S15
29. European Pharmacopoeia, 5th ed., Council of Europe: Strasbourg, 2000.
30. Bahal N., and Nahata M.C. Ann. Pharmacother. 26 (1992) 46-55
31. Welling P.G., Huang H., Hewitt P.F., and Lyons L.L. J. Pharm. Sci. 67 (1978) 764-766
32. Sturgill M.G., and Rapp R.P. Ann. Pharmacother. 26 (1992) 1099-1108
33. Langtry H.D., and Brogden R.N. Drugs 53 (1997) 973-1000
34. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 23 (1997) 3-25
35. Palm K., Stenberg P., Luthman K., and Artursson P. Pharm. Res. 14 (1997) 568-571
36. Veber D.F., Johnson S.R., Cheng H., Smith B.R., Ward K.W., and Kopple K.D. J. Med. Chem. 45 (2002) 2615-2623
37. Kurath P., Jones P.H., Egan R.S., and Perun T.J. Experientia 27 (1971) 362
38. Atkins P.J., Herbert T.O., and Jones N.B. Int. J. Pharm. 30 (1986) 199-207
39. Zini R., Fournet M.P., Barre J., Tremblay D., and Tillement J.P. Br. J. Clin. Pract. 42 (1988) 54
40. Dette G.A., Knothe H., and Knoulen G. Drugs Exp. Clin. Res. 13 (1987) 567-576
41. Kees F., Holstege A., Ittner K.P., Zimmermann M., Lock G., Schölmerich J., and Grobecker H. Aliment. Pharmacol. Ther. 14 (2000) 407-412
42. Nakagawa Y., Itai S., Yoshida T., and Nagai T. Chem. Pharm. Bull. 40 (1992) 725-728
43. Arimori K., Miyamoto S., Fukuda K., Nakamura C., and Nakano M. Biopharm. Drug Dispos. 19 (1998) 433-438
44. Djokic S., Kobrehel G., Lopotar N., Kamenar B., Nagl A., and Mrvos D. J. Chem. Res. 152 (1988) 1239-1261
45. Girard A.E., Girard D., English A.R., Gootz T.D., Cimochowski C.R., Faiella J.A., Haskell S.L., and Retsema J.A. Antimicrob. Agents Chemother. 31 (1987) 1948-1954
46. Kukina T.N., and Zorkii P.M. Vestn. Mosk. Univ. 22 (1981) 248-252
47. Williams D.E. Acta Crystallogr. B30 (1974) 71-77
48. Filippini G., and Gavezzotti A. Acta Crystallogr. B49 (1993) 868-880