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Research Article

Synthesis and evaluation of sulfate conjugated metronidazole as a colon-specific prodrug of metronidazole

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Pages 255-263 | Received 16 Jun 2011, Accepted 23 Oct 2011, Published online: 26 Nov 2011

References

  • Egan LJ, Sandborn WJ. (1998). Drug therapy of inflammatory bowel disease. Drugs Today, 34, 431–446.
  • Freeman CD, Klutman NE, Lamp KC. (1997). Metronidazole. A therapeutic review and update. Drugs, 54, 679–708.
  • Friend DR, Chang GW. (1985). Drug glycosides: Potential prodrugs for colon-specific drug delivery. J Med Chem, 28, 51–57.
  • Huijghebaert SM, Sim SM, Back DJ, Eyssen HJ. (1984). Distribution of estrone sulfatase activity in the intestine of germfree and conventional rats. J Steroid Biochem, 20, 1175–1179.
  • Jain A, Gupta Y, Jain SK. (2006). Azo chemistry and its potential for colonic delivery. Crit Rev Ther Drug Carrier Syst, 23, 349–400.
  • Jung Y, Kim YM. (2010). What should be considered on design of a colon-specific prodrug? Expert Opin Drug Deliv, 7, 245–258.
  • Jung YJ, Lee JS, Kim YM. (2000). Synthesis and in vitro/in vivo evaluation of 5-aminosalicyl-glycine as a colon-specific prodrug of 5-aminosalicylic acid. J Pharm Sci, 89, 594–602.
  • Jung YJ, Doh MJ, Kim IH, Kong HS, Lee JS, Kim YM. (2003). Prednisolone 21-sulfate sodium: A colon-specific pro-drug of prednisolone. J Pharm Pharmacol, 55, 1075–1082.
  • Kapoor K, Chandra M, Nag D, Paliwal JK, Gupta RC, Saxena RC. (1999). Evaluation of metronidazole toxicity: A prospective study. Int J Clin Pharmacol Res, 19, 83–88.
  • Kim D, Hong S, Jung S, Jung Y, Kim YM. (2009). Synthesis and evaluation of N-nicotinoyl-2-{2-(2-methyl-5-nitroimidazol-1-yl)ethyloxy}-D,L-glycine as a colon-specific prodrug of metronidazole. J Pharm Sci, 98, 4161–4169.
  • Kim H, Kong H, Choi B, Yang Y, Kim Y, Lim MJ, Neckers L, Jung Y. (2005). Metabolic and pharmacological properties of rutin, a dietary quercetin glycoside, for treatment of inflammatory bowel disease. Pharm Res, 22, 1499–1509.
  • Kim IH, Kong HS, Choi BI, Kim YS, Kim HJ, Yang YW, Jung YJ, Kim YM. (2006). Synthesis and in vitro properties of dexamethasone 21-sulfate sodium as a colon-specific prodrug of dexamethasone. Drug Dev Ind Pharm, 32, 389–397.
  • Kinouchi T, Ohnishi Y. (1983). Purification and characterization of 1-nitropyrene nitroreductases from Bacteroides fragilis. Appl Environ Microbiol, 46, 596–604.
  • Krishnaiah YS, Seetha Devi A, Nageswara Rao L, Bhaskar Reddy PR, Karthikeyan RS, Satyanarayana V. (2001). Guar gum as a carrier for colon specific delivery; influence of metronidazole and tinidazole on in vitro release of albendazole from guar gum matrix tablets. J Pharm Pharm Sci, 4, 235–243.
  • Krishnaiah YS, Bhaskar Reddy PR, Satyanarayana V, Karthikeyan RS. (2002). Studies on the development of oral colon targeted drug delivery systems for metronidazole in the treatment of amoebiasis. Int J Pharm, 236, 43–55.
  • Lamp KC, Freeman CD, Klutman NE, Lacy MK. (1999). Pharmacokinetics and pharmacodynamics of the nitroimidazole antimicrobials. Clin Pharmacokinet, 36, 353–373.
  • Lau AH, Lam NP, Piscitelli SC, Wilkes L, Danziger LH. (1992). Clinical pharmacokinetics of metronidazole and other nitroimidazole anti-infectives. Clin Pharmacokinet, 23, 328–364.
  • Lee JS, Jung YJ, Kim YM. (2001). Synthesis and evaluation of N-acyl-2-(5-fluorouracil-1-yl)-D,L-glycine as a colon-specific prodrug of 5-fluorouracil. J Pharm Sci, 90, 1787–1794.
  • Leitsch D, Kolarich D, Wilson IB, Altmann F, Duchêne M. (2007). Nitroimidazole action in Entamoeba histolytica: A central role for thioredoxin reductase. PLoS Biol, 5, e211.
  • Loft S, Poulsen HE. (1989). Metabolism of metronidazole and antipyrine in isolated rat hepatocytes. Influence of sex and enzyme induction and inhibition. Biochem Pharmacol, 38, 1125–1136.
  • Ludlum DB, Colinas RJ, Kirk MC, Mehta JR. (1988). Reaction of reduced metronidazole with guanosine to form an unstable adduct. Carcinogenesis, 9, 593–596.
  • Marteau P, Seksik P, Shanahan F. (2003). Manipulation of the bacterial flora in inflammatory bowel disease. Best Pract Res Clin Gastroenterol, 17, 47–61.
  • McLeod AD, Tolentino L, Tozer TN. (1994). Glucocorticoid-dextran conjugates as potential prodrugs for colon-specific delivery: Steady-state pharmacokinetics in the rat. Biopharm Drug Dispos, 15, 151–161.
  • Mundargi RC, Patil SA, Agnihotri SA, Aminabhavi TM. (2007). Development of polysaccharide-based colon targeted drug delivery systems for the treatment of amoebiasis. Drug Dev Ind Pharm, 33, 255–264.
  • Petri WA Jr. (2003). Therapy of intestinal protozoa. Trends Parasitol, 19, 523–526.
  • Sinha VR, Kumria R. (2001). Colonic drug delivery: Prodrug approach. Pharm Res, 18, 557–564.
  • Stanley SL Jr. (2003). Amoebiasis. Lancet, 361, 1025–1034.
  • Van Eldere J, Robben J, De Pauw G, Merckx R, Eyssen H. (1988). Isolation and identification of intestinal steroid-desulfating bacteria from rats and humans. Appl Environ Microbiol, 54, 2112–2117.

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