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Chemical Compound Review

Selacryn     2-(2,3-dichloro-4-thiophen-2- ylcarbonyl...

Synonyms: Diflurex, Ticrex, Ticrynafen, Thienylic acid, Tienilic acid, ...
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Disease relevance of ANP 3624


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Chemical compound and disease context of ANP 3624


Biological context of ANP 3624


Anatomical context of ANP 3624


Associations of ANP 3624 with other chemical compounds


Gene context of ANP 3624


Analytical, diagnostic and therapeutic context of ANP 3624

  • Tienilic acid hepatitis sera that were preadsorbed on microsomes from untreated rats (to remove autoantibodies), poorly recognized untreated hepatocytes in flow cytometry experiments, but better recognized tienilic acid-treated hepatocytes [9].
  • Hemodialysis (5 hr) reduced levels of ticrynafen by 38% but had less effect on metabolite levels [18].
  • Application of this HPLC/ESI-MS technique made the detection of the covalent modification to P450 2C9 following mechanism-based inactivation by tienilic acid possible [26].
  • METHODS: In normotensive eyes, facility (perfusion) was measured shortly before and after bolus or exchange intracameral infusion of ticrynafen or vehicle in opposite eyes, and 3.5 to 4.5 hours after 5 days of twice-daily 2% ticrynafen or vehicle ointment [19].
  • Urinary output and serum or plasma levels of ticrynafen and its two metabolites were measured in specimens from human volunteers receiving one 250-mg tablet [27].


  1. Acute renal failure from ticrynafen. Selby, T. N. Engl. J. Med. (1979) [Pubmed]
  2. Evaluation of a new uricosuric diuretic--ticrynafen. Kosman, M.E. JAMA (1979) [Pubmed]
  3. Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. Homberg, J.C., Abuaf, N., Helmy-Khalil, S., Biour, M., Poupon, R., Islam, S., Darnis, F., Levy, V.G., Opolon, P., Beaugrand, M. Hepatology (1985) [Pubmed]
  4. Presence of functional cytochrome P-450 on isolated rat hepatocyte plasma membrane. Loeper, J., Descatoire, V., Maurice, M., Beaune, P., Feldmann, G., Larrey, D., Pessayre, D. Hepatology (1990) [Pubmed]
  5. Immune mechanisms in tienilic acid associated hepatotoxicity. Neuberger, J., Williams, R. Gut (1989) [Pubmed]
  6. Ticrynafen: a novel uricosuric antihypertensive natriuretic agent. de Carvalho, J.G., Dunn, F.G., Chrysant, S.G., Frohlich, E.D. Arch. Intern. Med. (1978) [Pubmed]
  7. Adverse reactions associated with ticrynafen use. McLain, D.A., Garriga, F.J., Kantor, O.S. JAMA (1980) [Pubmed]
  8. Clinical study of ticrynafen. A new diuretic, antihypertensive, and uricosuric agent. Nemati, M., Kyle, M.C., Freis, E.D. JAMA (1977) [Pubmed]
  9. Antigenic targets in tienilic acid hepatitis. Both cytochrome P450 2C11 and 2C11-tienilic acid adducts are transported to the plasma membrane of rat hepatocytes and recognized by human sera. Robin, M.A., Maratrat, M., Le Roy, M., Le Breton, F.P., Bonierbale, E., Dansette, P., Ballet, F., Mansuy, D., Pessayre, D. J. Clin. Invest. (1996) [Pubmed]
  10. Biochemical and haematological changes induced by tienilic acid combined with propranolol in essential hypertension. Pearson, R.M., Bulpitt, C.J., Havard, C.W. Lancet (1979) [Pubmed]
  11. Ticrynafen-racemic warfarin interaction: hepatotoxic or stereoselective? O'Reilly, R.A. Clin. Pharmacol. Ther. (1982) [Pubmed]
  12. Specificity of in vitro covalent binding of tienilic acid metabolites to human liver microsomes in relationship to the type of hepatotoxicity: comparison with two directly hepatotoxic drugs. Lecoeur, S., Bonierbale, E., Challine, D., Gautier, J.C., Valadon, P., Dansette, P.M., Catinot, R., Ballet, F., Mansuy, D., Beaune, P.H. Chem. Res. Toxicol. (1994) [Pubmed]
  13. Tienilic acid enhances hyperbilirubinemia in Eisai hyperbilirubinuria rats through hepatic multidrug resistance-associated protein 3 and heme oxygenase-1 induction. Nishiya, T., Kataoka, H., Mori, K., Goto, M., Sugawara, T., Furuhama, K. Toxicol. Sci. (2006) [Pubmed]
  14. Renal function during therapy in patients with congestive cardiac failure. Ticrynafen vs. hydrochlorothiazide. Smith, J.W., Clements, P. Nephron (1979) [Pubmed]
  15. Human anti-endoplasmic reticulum autoantibodies appearing in a drug-induced hepatitis are directed against a human liver cytochrome P-450 that hydroxylates the drug. Beaune, P., Dansette, P.M., Mansuy, D., Kiffel, L., Finck, M., Amar, C., Leroux, J.P., Homberg, J.C. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  16. Effects of diuretics on urate and calcium excretion. Yü, T., Berger, L., Sarkozi, L., Kaung, C. Arch. Intern. Med. (1981) [Pubmed]
  17. Renal transport of urate during diuretic-induced hypouricemia. Reese, O.G., Steele, T.H. Am. J. Med. (1976) [Pubmed]
  18. Ticrynafen in anephric patients: effects on uric acid and pharmacokinetics. Murray, T.G., Brown, S., Dubb, J.W., Hwang, B.Y., Stote, R.M. Clin. Pharmacol. Ther. (1980) [Pubmed]
  19. Effect of ticrynafen on aqueous humor dynamics in monkeys. Croft, M.A., Wang, R.F., Podos, S.M., Neufeld, A.H., Kaufman, P.L. Arch. Ophthalmol. (1998) [Pubmed]
  20. Comparative effects of ticrynafen and hydrochlorothiazide on blood pressure, renal function, serum uric acid and electrolytes, and body fluid spaces in hypertensive man. Bauer, J.H., Brooks, C.S. Nephron (1979) [Pubmed]
  21. Ticrynafen and hydrochlorothiazide in hypertension. Okun, R., Beg, M. Clin. Pharmacol. Ther. (1978) [Pubmed]
  22. Thiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid. López-Garcia, M.P., Dansette, P.M., Mansuy, D. Biochemistry (1994) [Pubmed]
  23. The substrate binding site of human liver cytochrome P450 2C9: an NMR study. Poli-Scaife, S., Attias, R., Dansette, P.M., Mansuy, D. Biochemistry (1997) [Pubmed]
  24. Genetic polymorphism of human cytochrome P-450 (S)-mephenytoin 4-hydroxylase. Studies with human autoantibodies suggest a functionally altered cytochrome P-450 isozyme as cause of the genetic deficiency. Meier, U.T., Meyer, U.A. Biochemistry (1987) [Pubmed]
  25. Cytochrome P450 enzymes and UDP-glucuronosyltransferases as hepatocellular autoantigens. Obermayer-Straub, P., Manns, M.P. Mol. Biol. Rep. (1996) [Pubmed]
  26. Electrospray ionization mass spectrometric analysis of intact cytochrome P450: identification of tienilic acid adducts to P450 2C9. Koenigs, L.L., Peter, R.M., Hunter, A.P., Haining, R.L., Rettie, A.E., Friedberg, T., Pritchard, M.P., Shou, M., Rushmore, T.H., Trager, W.F. Biochemistry (1999) [Pubmed]
  27. GLC determination of ticrynafen and its metabolites in urine, serum, and plasma of humans and animals. Hwang, B., Konicki, G., Dewey, R., Miao, C. Journal of pharmaceutical sciences. (1978) [Pubmed]
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