Synthesis and antinociceptive activity of orally active opioid peptides: Improvement of oral bioavailability by esterification

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 7, 2003, Pages 759-771

  Ogawa, Tadashi ^a   Araki, Mamoru ^a   Miyamae, Tetsuhisa ^a   Okayama, Toru ^a   Hagiwara, Masaki ^a   Sakurada, Shinobu ^b   Morikawa, Tadanori ^a  

^a Daiichi Fine Chemical Co Ltd   (Japan)

^b TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Chemical modification; Dermorphin tetrapeptide analog; Lipophilicity; Oral bioavailability

Indexed keywords

MORPHINE; OPIATE PEPTIDE; ANALGESIC AGENT;

ACETYLATION; ACYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CARBONYLATION; CARBOXY TERMINAL SEQUENCE; DOSE RESPONSE; DRUG BIOAVAILABILITY; ESTERIFICATION; MOUSE; NONHUMAN; PRESSURE; ANIMAL; BIOAVAILABILITY; DRUG EFFECT; METHODOLOGY; ORAL DRUG ADMINISTRATION; PAIN ASSESSMENT; SYNTHESIS;

ADMINISTRATION, ORAL; ANALGESICS; ANIMALS; BIOLOGICAL AVAILABILITY; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTERIFICATION; MICE; OPIOID PEPTIDES; PAIN MEASUREMENT;

EID: 1542681056     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.759     Document Type: Article

References (35)

1. i, isopropyl; TEA, triethylamine; EDC·HCl, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride.
2. Erspamer V., Melchiorri P., "Growth Hormone and Other Biological Peptides," eds. by Pecil A., Muller E. E., Excerpta Medica, Amsterdam, 1980, pp. 185-200.
3. De Castiglione R., Faoro F., Perseo G., Piani S., Santangelo F., Melchiorri P., Erspamer G. F., Erspamer V., Guglietta A., Peptides, 2, 265-269 (1981).
4. De Castiglione R., Rossi A. C., Peptides, 6 (Suppl. 3), 117-125 (1985).
5. Melchiorri P., Negri L., Gen. Pharmac., 27, 1099-1107 (1996).
6. Suzuki K., Fujita H., Matsui M., Sasaki Y., Sakurada S., Sakurada T., Kisara K., Chem. Pharm. Bull., 33, 4865-4869 (1985).
7. Sasaki Y., Matsui M., Fujita H., Hosono M., Taguchi M., Suzuki K., Sakurada S., Sato T., Sakurada T., Kisara K., Chem. Pharm. Bull., 33, 1528-1536 (1985).
8. Sato T., Sakurada S., Sakurada T., Furuta S., Chaki K., Kisara K., Sasaki Y., Suzuki K., J. Pharmacol. Exp. Ther., 242, 654-659 (1987).
9. Kisara K., Sakurada S., Sakurada T., Sasaki Y., Sato T., Suzuki K., Watanabe H., Br. J. Pharmacol., 87, 183-189 (1986).
10. Fujita H., Sasaki Y., Kohno H., Ohkubo Y., Ambo A., Suzuki K., Hino M., Chem. Pharm. Bull., 38, 2197-2200 (1990).
11. Ogawa T., Miyamae T., Okayama T., Hagiwara M., Sakurada S., Morikawa T., Chem. Pharm. Bull., 50, 771-780 (2002).
12. Ogawa T., Miyamae T., Murayama K., Okuyama K., Okayama T., Hagiwara M., Sakurada S., Morikawa T., J. Med. Chem., 45, 5081-5089 (2002).
13. Humphrey M. J., Ringrose P. S., Drug Metab. Rev., 17, 283-310 (1986).
14. Lee V. H. L., Yamamoto A., Adv. Drug Deliv. Rev., 4, 171-207 (1990).
15. Bocci V., Adv. Drug Deliv. Rev., 4, 149-169 (1990).
16. Modi N. B., J. Control. Release, 29, 269-281 (1994).
17. Zhou X. H., J. Control. Release, 29, 239-252 (1994).
18. Amidon G. L., Lee H. J., Ann. Rev. Pharmacol. Toxicol., 34, 321-341 (1994).
19. Pauletti G. M., Gangwar S., Knipp G. T., Nerurkar M. M., Okumu F. W., Tamura K., Siahaan T. J., Borchardt R. T., J. Control. Release, 41, 3-17 (1996).
20. Pauletti G. M., Gangwar S., Siahaan T. J., Aubé J., Borchardt R. T., Adv. Drug Deliv. Rev., 27, 235-256 (1997).
21. Samanen J., Wilson G., Smith P. L., Lee C., Bondinell W., Ku T., Rhodes G., Nichols A., J. Pharm. Pharmacol., 48, 119-135 (1996).
22. Sasaki Y., Matsui M., Fujita H., Hosono M., Taguchi M., Suzuki K., Sakurada S., Sato T., Sakurada T., Kisara K., Neuropeptides, 5, 391-394 (1985).
23. Marastoni M., Salvadori S., Baloboni G., Andrea P., Marzola G., Tomatis R., J. Med. Chem., 30, 1538-1542 (1987).
24. Chaki K., Sakurada S., Sakurada T., Kisara K., Suzuki K., Life Sciences, 46, 1671-1678 (1990).
25. Litchfield J. T., Wilcoxon F. A., J. Pharmacol. Exp. Ther., 96, 99-113 (1949).
26. Bodin N. O., Ekstrom B., Forsgren U., Jalar L. P., Magni L., Ramsay C. H., Sjoberg B., Antimicrob. Agents Chemother., 8, 518-525 (1975).
27. Daehne W. V., Frederiksen E., Gundersen E., Lund F., Morch P., Pertersen H. L., Roholt K., Tybring L., Godtfredsen W. O., J. Med. Chem., 13, 607-612 (1970).
28. Clayton J. P., Cole N., Elson S. W., Ferres H., Antimicrob. Agents Chemother., 5, 670-671 (1974).
29. Robinson S. L., Rowbotham D. J., Smith G., Anaesthesia, 46, 538-540 (1991).
30. "British National Formulary," Vol. 39, British Medical Association and Royal Pharmaceutical Society of Great Britain, London, 2000.
31. Lipinski C. A., J. Pharmacol. Toxicol. Methods, 44, 235-249 (2000).
32. Bodor N., Farag H. H., Brewster M. E., Science, 214, 1370-1372 (1981).
33. Derek R. P., Robert G. T., U.S. Patent 4820857 (1989).
34. Sakamoto F., Ikeda S., Tsukamoto G., Chem. Pharm. Bull., 31, 2698-2707 (1983).
35. Sakurada S., Sakurada T., Jin H., Sato T., Kisara K., Sasaki Y., Suzuki K., J. Pharm. Pharmacol., 34, 750-751 (1982).