Mechanism of intestinal absorption of an orally active β-lactam prodrug: Uptake and transport of carindacillin in Caco-2 cells

Journal of Pharmacology and Experimental Therapeutics

Volumn 290, Issue 3, 1999, Pages 958-964

  Li, Yin Hua ^a   Ito, Kiyomi ^a   Tsuda, Yasuyuki ^a   Kohda, Rikako ^a   Yamada, Hideo ^a,b   Itoh, Tomoo ^a  

^a KITASATO UNIVERSITY   (Japan)

^b MUSASHINO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; BETA LACTAM ANTIBIOTIC; CARBENICILLIN; CARBONYL CYANIDE 4 (TRIFLUOROMETHOXY)PHENYLHYDRAZONE; CARINDACILLIN; PRODRUG; SALICYLIC ACID DERIVATIVE;

ARTICLE; DOSE TIME EFFECT RELATION; DRUG DIFFUSION; DRUG MECHANISM; DRUG STRUCTURE; DRUG TRANSPORT; HUMAN; HUMAN CELL; INTESTINE ABSORPTION; PRIORITY JOURNAL; TEMPERATURE DEPENDENCE;

ADMINISTRATION, ORAL; ANTI-BACTERIAL AGENTS; ANTIMETABOLITES; BIOLOGICAL TRANSPORT, ACTIVE; CACO-2 CELLS; CARBENICILLIN; DRUG STABILITY; HUMANS; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; INTESTINAL ABSORPTION; KINETICS; LACTIC ACID; PENICILLINS; PRODRUGS; SODIUM AZIDE;

EID: 0032810558     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. Annaert P, Kinget R, Naesens L, Clercq ED and Augustijns P (1997) Transport, uptake and metabolism of the bis(pivaloyloxymethyl)-ester prodrug of 9-(2-phosphonylmethoxyethyl)adenine in an in vitro cell culture system of the intestinal mucosa (Caco-2). Pharm Res 14:492-496.
2. Artursson P and Karlsson J (1991) Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880-885.
3. Bird AE and Steele BR (1982) Nuclear magnetic resonance and circular dichroism of penicillins derived from disubstituted acetic acids. J Chem Soc Perkin Trans 1:563-569.
4. Bradford MM (1976) A rapid and sensitive method for the determination of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
5. Clayton JP, Cole M, Elson SW, Hardy KD, Mizen LW and Sutherland R (1975) Preparation, hydrolysis, and oral absorption of α-carboxy esters of carbenicillin. J Med Chem 18:172-177.
6. Dantzig AH and Bergin L (1990) Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2. Biochim Biophys Acta 1027:211-217.
7. Dantzig AH, Duckworth DC and Tabas LB (1994) Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells. Biochim Biophys Acta 1191:7-13.
8. Duizer E, Penninks AH, Stenhuis WH and Groten JP (1997) Comparison of permeability characteristics of the human colonic Caco-2 and rat small intestinal IEC-18 cell lines. J Control Release 49:39-49.
9. Ganapathy ME, Huang W, Wang H, Ganapathy V and Leibach FH (1998) Valacyclovir: A substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun 246:470-475.
10. Grasset E, Pinto M, Dussaulx E, Zweibaum A and Desjeux J-F (1984) Epithelial properties of human colonic carcinoma cell line Caco-2: Electrical parameters. Am J Physiol 247:C260-C267.
11. Hilgers AR, Conradi RA and Burton PS (1990) Caco-2 cell monolayers as a model for drug transport across the intestinal mucosa. Pharm Res 7:902-910.
12. Inui KI, Yamamoto M and Saito H (1992) Transepithelial transport of oral cephalosporins by monolayers of intestinal epithelial cell line Caco-2: Specific transport systems in apical and basolateral membranes. J Pharmacol Exp Ther 261:195-201.
13. Itoh T and Yamada H (1995) Diastereomeric β-lactam antibiotics: Analytical methods, isomerization and stereoselective pharmacokinetics. J Chromatogr A 694: 195-208.
14. Itoh T, Tanno M, Li YH and Yamada H (1998) Transport of phenethicillin into rat intestinal brush border membrane vesicles: Role of the monocarboxylic acid transport system. Int J Pharm 172:103-112.
15. +/dipeptide cotransport system in human intestinal cell line Caco-2: Regulation by cell growth. Pharm Res 12:1483-1487.
16. Muranushi N, Yoshikawa T, Yoshida M, Oguma T, Hirano K and Yamada H (1989) Transport characteristics of ceftibuten, a new oral cephem, in rat intestinal brush-border membrane vesicles: Relationship to oligopeptide and amino β-lactam transport. Pharm Res 6:308-312.
17. Ogihara T, Tamai I, Takanaga H, Sai Y and Tsuji A (1996) Stereoselective and carrier-mediated transport of monocarboxylic acids across Caco-2 cells, Pharm Res 13:1828-1832.
18. + coupled uphill transport of aminocephalosporins via the dipeptide transport system in rabbit intestinal brush-border membrane. J Biol Chem 261:14130-14134.
19. Prasad PD, Ramamoorthy S, Leibach FH and Ganapathy V (1995) Molecular cloning of the human placental folate transporter. Biochem Biophys Res Commun 206: 681-687.
20. Sharom FJ (1997) The P-glycoprotein efflux pump: How does it transport drugs? J Membr Biol 160:161-175.
21. Takagi M, Taki Y, Sakane T, Nadai T, Sezaki H, Oku N and Yamashita S (1998) A new interpretation of salicylic acid transport across the lipid bilayer: Implications of pH-dependent but not carrier-mediated absorption from the gastrointestinal tract. J Pharmacol Exp Ther 288:1175-1180.
22. +/peptide cotransporters in rat renal brush border membrane. J Pharmacol Exp Ther 286:1037-1042.
23. Takanaga H, Tamai I and Tsuji A (1994) pH-Dependent and carrier-mediated transport of salicylic acid across Caco-2 cells. J Pharm Pharmacol 46:567-570.
24. Tamai I, Takanaga H, Maeda H, Sai Y, Ogihara T, Higashida H and Tsuji A (1995) Participation of a proton-cotransporter, MCT1, in the intestinal transport of monocarboxylic acids. Biochem Biophys Res Commun 214:482-489.
25. Tanigawara Y, Yamaoka K, Nakagawa T and Uno T (1982) Absorption kinetics of carbenicillin phenyl sodium and carbenicillin indanyl sodium in man. Chem Pharm Bull 30:2174-2180.
26. +-coupled dipeptide (glycylsarcosine) transport across apical and basal borders of human intestinal Caco-2 cell monolayers display distinctive characteristics. Biochim Biophys Acta 1151:237-245.
27. Tiruppathi C, Balkovetz DA, Ganapathy V, Miyamoto Y and Leibach FH (1988) A proton gradient, not a sodium gradient, is the driving force for the active transport of lactate in rabbit intestinal brush-border membrane vesicles. Biochem J 256: 219-223.
28. Tsuji A, Miyamoto E, Terasaki T and Yamana T (1982) Carbenicillin prodrugs: Kinetics of intestinal absorption competing degradation of the α-esters of carbenicillin and prediction of prodrug absorbability from quantitative structure-absorption rate relationship. J Pharm Sci 71:403-406.
29. Teuji A, Takanaga H, Tamai I and Terasaki T (1994) Transcellular transport of benzoic acid across Caco-2 cells by a pH-dependent and carrier-mediated transport mechanism. Pharm Res 11:30-37.
30. + gradient dependent and carrier-mediated transport of cefixime, a new cephalosporin antibiotic, across brush-border membrane vesicles from rat small intestine. J Pharmacol Exp Ther 241:594-601.
31. Tsuji A, Tamai I, Nakanishi M, Terasaki T and Hamano S (1993) Intestinal brush-border transport of the oral cephalosporin antibiotic, cefdinir, mediated by the dipeptide and monocarboxylic acid transport systems in rabbits. J Pharm Pharmacol 45:996-998.
32. Yamana T, Tsuji A and Mizukami Y (1974) Kinetic approach to the development in β-lactam antibiotics. Comparative stability of semisynthetic penicillin and 6-aminopenicillin acid in aqueous solution. Chem Pharm Bull 22:1186-1197.