Skip to main content
Log in

Phase transfer synthesis of sulphamerazine-N1-(methyl 2,3,4-tri-O-acetyl-β-D-glucuronide)

  • Notes
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Sulphamerazine-N1-(methyl 2,3,4-tri-O-acetyl-β-D-glucuronide) was successfully synthesized and characterized by proton NMR and mass spectrometry for the metabolic study of sulphamerazine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. Dutton G.J.:Glucuronide of drugs and other compounds. CRS Press Inc., Florida, (1980).

    Google Scholar 

  2. Bridges J.W., Kibby M.R. and Williams R.T.: The Structure of the glucuronide of sulphadimethoxine formed in man.Biochem. J. 96, 829 (1965).

    PubMed  CAS  Google Scholar 

  3. Uno T. and Ueda M.: Studies on the metabolism of sulphathiazole. A new sulphathiazole-glucuronic acid conjugate in the human urine.Chem. Pharm. Bull. 11, 709 (1963).

    PubMed  CAS  Google Scholar 

  4. Kadlubar F.F., Miller J.A. and Miller E.C.: Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis.Cancer Research,37, 805 (1977).

    PubMed  CAS  Google Scholar 

  5. Wooley J.L. and Siegel C.W.: Metabolism and disposition by the rat of35S-sulphadiazine alone and in the presence of trimethoprim.Drug Metab. and Dispos. 7, 94 (1979).

    Google Scholar 

  6. Woolfenden R.D.G., in:Analytical profiles of drug substances, Vol. 6 Ed. Florey K., Academic Press, New York, p. 515 (1977).

    Google Scholar 

  7. Nielsen P.: The metabolism of four sulphoamides in cows.Biochem. J. 136, 1039 (1973).

    PubMed  CAS  Google Scholar 

  8. Paulson G.D., Giddings J.M., Lamoureux C.H., Mansager E.R. and Struble C.B.: The isolation and identification of14C-sulphamethazine metabolites in the tissues and excreta of swine.Drug Metab. and Dispos. 9, 142 (1981).

    CAS  Google Scholar 

  9. Matusik J.E., Barnes C.J., Newkird D.R. and Fazio T.: Drug residues in animal tissues.J. Assoc. Off. Anal. Chem. 65, 828 (1982).

    PubMed  CAS  Google Scholar 

  10. Giera D.D., Abdulla R.F., Occolowitz J.L., Dorman D.E., Mertz J.L. and Sieck R.F.: Isolation and identification of a polar sulphamethazine metabolite from swine tissues.J. Agric. Food Chem. 30, 260 (1982).

    Article  CAS  Google Scholar 

  11. Dess D., Keline H.P., Weinberg D.V., Kaufman R.J. and Sidhu R.S.: Phase transfercatalysed synthesis of acetylated aryl β-D-glucopyranosides and aryl β-D-galactopyranoside.Synthesis 13, 883 (1981).

    Article  Google Scholar 

  12. Tang B.K., Kalow W. and Grey A.A.: Metabolic fate of phenobarbital in man, N-glucoside formation.Drug Metab. and Dispos. 7, 315 (1979).

    CAS  Google Scholar 

  13. Al-Sharifi M.A.M., Ph. D. Thesis, London (1982).

  14. Stubbs R.J. Ph. D. Thesis, London (1982).

  15. Soine W.H., Bhargava V.O. and Garretson L.K.: Direct detection of 1-(β-D-glucopyranosyl) phenobarbital in human urine.Drug Metab. and Dispos. 12, 792 (1984).

    CAS  Google Scholar 

  16. Berrange B., Twine C.E., Hennessee G.L. and Carroll F.I.: Synthesis of morphine 3-glucuronide.Synth. Commun. 5, 231 (1975).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ahmad, B., Powell, J.W. Phase transfer synthesis of sulphamerazine-N1-(methyl 2,3,4-tri-O-acetyl-β-D-glucuronide). Arch. Pharm. Res. 11, 244–246 (1988). https://doi.org/10.1007/BF02861316

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02861316

Keywords

Navigation