Metabolism of isobutylnaphthyl acetic acid in rats: determination of the chemical structures of metabolites

  • G. Achtert
  • F. Borchers
  • C. Jacquot
  • M. O. Christen
Original Papers


After oral and intravenous administration of radiolabelled isobutylnaphthyl acetic acid (INAA) to rats two metabolites were isolated from urine and plasma by HPLC. Field desorption, high resolution electron impact mass spectrometry as well as GC-MS after derivatization were used for structure elucidation and identification of the metabolites. The main biotransformation product in rat urine was found to be 5-(2′-hydroxy-2′-methyl-propyl)-l-naphthyl acetic acid (M1). The main metabolite in plasma was derived and was found to be 5-(2′-carboxypropyl)-l-naphthyl acetic acid (M2).

Key words

Isobutylnaphthyl acetic acid metabolism rat mass spectrometry 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Adams S.S., Buckler J.W. (1979): Ibuprofen and Flurbiprofen. Clin. Rheum., Dis., 5, 359–379.Google Scholar
  2. 2.
    Julou L., Guyonnet J.C., Dugrot R., et al. (1971): Etude des propriétés pharmacologiques d’un nouvel anti-inflammatoire l’acide (benzoyl-3 phenyl)-2 propionique (19583 RP). J. Pharmacol., 2, 259–286.Google Scholar
  3. 3.
    Brogden R.M., Pinder R.M., Sawyer P.R., Speight T.M., Avery G.S. (1975): Naproxen: a review of its pharmacological properties and therapeutic efficacy and use. Drugs, 9, 326–363.CrossRefPubMedGoogle Scholar
  4. 4.
    Kelley V.E., Izui S., Halushka P.V. (1982): Effect of Ibuprofen, a fatty acid cyclo oxygenase inhibitor, on murine lupus. Clin. Immunol. Immunopathol., 25, 223–231.CrossRefPubMedGoogle Scholar
  5. 5.
    Rafanell J.G, Forn J. (1979): Correlation between anti-inflammatory activity and inhibition of prostaglandin biosynthesis induced by various non-steroidal anti-inflammatory agents. Arzneimittelforsch., 29, 630–633.Google Scholar
  6. 6.
    Goodman, Gilman’s (1980): The pharmacological basis of therapeutics. Drug therapy of inflammation p. 682–728. Macmillian, New York.Google Scholar
  7. 7.
    Jacquot C., Payan-Lepain E., Christen M.O., et al. (1989): Pharmacokinetics and metabolism of14C isobutylnaphthyl acetic acid in rat. Eur. J. Drug Metab. Pliarmacokinet., submitted.Google Scholar
  8. 8.
    Adams S.S., Cliffe E.E., Lessel B., Nicholson J.S. (1967): Some biological properties of 2-(4-isobutylphenyl)-propionic acid. J. Pharm. Sci., 56, 1686.CrossRefPubMedGoogle Scholar
  9. 9.
    Brooks CJ.W., Gilbert M.T. (1974): Studies of urinary metabolites of 2-(4-isobutylphenyl)-propionic acid by gas chromatography-mass spectrometry. J. Chromatogr., 99, 541–551.CrossRefPubMedGoogle Scholar
  10. 10.
    Pettersen J.E., Ulsaker G.A., Jellum E. (1978): Studies on the metabolism of 2,4′-isobutylphenylpropionic acid (Ibuprofen) by gas chromatography and mass spectrometry. Dialysis fluid, a convenient medium for studies on drug metabolism. J. Chromatogr., 145, 413–420.CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag 1989

Authors and Affiliations

  • G. Achtert
    • 1
  • F. Borchers
    • 1
  • C. Jacquot
    • 2
  • M. O. Christen
    • 3
  1. 1.Sparte PharmaKali-Chemie A.G.HannoverFRG
  2. 2.Laboratoire Pharmacocinétique expérimentaleFaculté de Pharmacie Paris XIChatenay MalabryFrance
  3. 3.Laboratoires de Thérapeutique Moderne L.T.M.SuresnesFrance

Personalised recommendations