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Chemical Compound Review

Probecid     4-(dipropylsulfamoyl)benzoic acid

Synonyms: Benecid, Benemid, Benuryl, probenecid, Pro-Cid, ...
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Disease relevance of Ethamide


Psychiatry related information on Ethamide


High impact information on Ethamide


Chemical compound and disease context of Ethamide


Biological context of Ethamide

  • Quinine sulphate prevented the probenecid effect but had no effect on zidovudine kinetics when taken without probenecid by four other subjects [15].
  • This dye movement was not appreciably delayed by pretreatment of cells with 5 mM probenecid or chilling the monolayer to 5 degrees C, suggesting that dye movement was due to passive permeation through a membrane pore rather than active transport [20].
  • Moreover, kinetic analysis of inhibition by probenecid suggests that it is competitive with respect to either OH- or Cl-. These results suggest that anions and the anion transport system may play a role in exocytosis of a polypeptide hormone [21].
  • Furthermore, the pHi recovery following NH4Cl exposure was accelerated by isoproterenol in the presence of probenecid, indicating that the Na(+)-HCO3- cotransport and/or the Na(+)-H+ antiport also could be activated.(ABSTRACT TRUNCATED AT 250 WORDS)[22]
  • Cell death was specific as it was also present in a human proximal tubular epithelial cell line (HK-2), but not in a human kidney fibroblast cell line, and was prevented by probenecid [23].

Anatomical context of Ethamide

  • We found that probenecid also reversibly inhibited sequestration of dye, indicating that sequestration of dye within cytoplasmic vacuoles was also mediated by organic anion transporters [24].
  • Central nervous system metabolism in six children and one adult with the syndrome of chronic multiple tics was studied by measuring the accumulation of acid metabolites of dopamine and serotonin (homovanillic acid [HVA] and 5-hydroxyindole-acetic acid [5-HIAA], respectively) in the CSF following probenecid administration [5].
  • Disodium 4-acetamido-4'-isothiocyanostilbene-2,2'-disulfonate (SITS) and probenecid, which are known to block anion transport in the erythrocyte, also cause a dose-dependent 90%-100% inhibition of release [21].
  • Therefore, LTC4 export from cells of bone marrow origin occurs through a probenecid-sensitive membrane carrier shared by other glutathione conjugates and distinct from the LTB4 carrier export system [25].
  • When cells preloaded with LTC4 were resuspended in incremental concentrations of the organic acid transport inhibitor, probenecid, there was a dose-dependent decrease in LTC4 release; GS-DNP and probenecid inhibited LTC4 release in a cumulative fashion, whereas neither inhibited the release of LTB4 from preloaded nondifferentiated HL-60 cells [25].

Associations of Ethamide with other chemical compounds


Gene context of Ethamide

  • We evaluated the activity of these drugs in combination with PSC833, a P-gp inhibitor, and/or probenecid, an MRP1 inhibitor [31].
  • Moreover, coadministration of probenecid and other MRP2-stimulating drugs might lead to unforeseen drug-drug interactions by stimulating MRP2 function, potentially leading to suboptimal levels of taxanes and other anticancer drugs in plasma and tumor [32].
  • DESIGN AND METHODS: MRD cells were identified using leukemia-associated phenotypes combined with a fluorescent probe assay with substrate/modulator: Syto16/ PSC833 (Pgp), calcein-AM/probenecid (MRP) and BODIPY-prazosin/Ko143 (BCRP); efflux profiles were directly compared with blasts at diagnosis and relapse from the same patient [33].
  • This effect of probenecid on MDR was associated with an increased accumulation of DNR and VCR and correction of the altered subcellular distribution of DNR [34].
  • The K(i) value of probenecid for hOAT3, but not for hOATP1B3, was significantly lower than the maximum unbound plasma concentration of probenecid at clinical dosages [35].

Analytical, diagnostic and therapeutic context of Ethamide


  1. Effect of treatment regimens for Neisseria gonorrhoeae on simultaneous infection with Chlamydia trachomatis. Stamm, W.E., Guinan, M.E., Johnson, C., Starcher, T., Holmes, K.K., McCormack, W.M. N. Engl. J. Med. (1984) [Pubmed]
  2. Therapy of gonorrhea. Comparison of trimethoprim-sulfamethoxazole and ampicillin. Sattler, F.R., Ruskin, J. JAMA (1978) [Pubmed]
  3. Cephalexin-related nephropathy. Verma, S., Kieff, E. JAMA (1975) [Pubmed]
  4. Urea secretion by the straight segment of the proximal tubule. Kawamura, S., Kokko, J.P. J. Clin. Invest. (1976) [Pubmed]
  5. Chronic, multiple tics of Gilles de la Tourette's disease. CSF acid monoamine metabolites after probenecid administration. Cohen, D.J., Shaywitz, B.A., Caparulo, B., Young, J.G., Bowers, M.B. Arch. Gen. Psychiatry (1978) [Pubmed]
  6. Intravenous probenecid loading. Effects on plasma and cerebrospinal fluid probenecid levels and on monoamine metabolites in cerebrospinal fluid. Kartzinel, R., Ebert, M.H., Chase, T.N. Neurology (1976) [Pubmed]
  7. Effects of probenecid on the pharmacokinetics and pharmacodynamics of adinazolam in humans. Golden, P.L., Warner, P.E., Fleishaker, J.C., Jewell, R.C., Millikin, S., Lyon, J., Brouwer, K.L. Clin. Pharmacol. Ther. (1994) [Pubmed]
  8. The effect of probenecid on spontaneous motor activity in rats. Lyness, W.H., Mycek, M.J. Neuropharmacology (1978) [Pubmed]
  9. Dopamine metabolism in depressions, psychoses, and Parkinson's disease: the problem of the specificity of biological variables in behaviour disorders. Praag, H.M., Korf, J., Lakke JPWF, n.u.l.l., Schut, T. Psychological medicine. (1975) [Pubmed]
  10. National gonorrhea therapy monitoring study: treatment results. Kaufman, R.E., Johnson, R.E., Jaffe, H.W., Thornsberry, C., Reynolds, G.H., Wiesner, P.J. N. Engl. J. Med. (1976) [Pubmed]
  11. Time-dependent effects of phenothiazines on dopamine turnover in psychiatric patients. Post, R.M., Goodwin, F.K. Science (1975) [Pubmed]
  12. Basolateral localization and export activity of the human multidrug resistance-associated protein in polarized pig kidney cells. Evers, R., Zaman, G.J., van Deemter, L., Jansen, H., Calafat, J., Oomen, L.C., Oude Elferink, R.P., Borst, P., Schinkel, A.H. J. Clin. Invest. (1996) [Pubmed]
  13. The folate receptor works in tandem with a probenecid-sensitive carrier in MA104 cells in vitro. Kamen, B.A., Smith, A.K., Anderson, R.G. J. Clin. Invest. (1991) [Pubmed]
  14. Structural and functional studies of ligandin, a major renal organic anion-binding protein. Kirsch, R., Fleischner, G., Kamisaka, K., Arias, I.M. J. Clin. Invest. (1975) [Pubmed]
  15. Probenecid and zidovudine metabolism. Kornhauser, D.M., Petty, B.G., Hendrix, C.W., Woods, A.S., Nerhood, L.J., Bartlett, J.G., Lietman, P.S. Lancet (1989) [Pubmed]
  16. Amoxycillin plus probenecid versus doxycycline for treatment of erythema migrans borreliosis. Dattwyler, R.J., Volkman, D.J., Conaty, S.M., Platkin, S.P., Luft, B.J. Lancet (1990) [Pubmed]
  17. Augmentation of the intracellular levels of polyglutamyl derivatives of methotrexate by vincristine and probenecid in Ehrlich ascites tumor cells. Fry, D.W., Yalowich, J.C., Goldman, I.D. Cancer Res. (1982) [Pubmed]
  18. Hypouricemia and hyperuricosuria as expressions of renal tubular damage in primary biliary cirrhosis. Izumi, N., Hasumura, Y., Takeuchi, J. Hepatology (1983) [Pubmed]
  19. Cytotoxicity of S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine in isolated rat kidney cells. Lash, L.H., Anders, M.W. J. Biol. Chem. (1986) [Pubmed]
  20. The parasitophorous vacuole membrane surrounding intracellular Toxoplasma gondii functions as a molecular sieve. Schwab, J.C., Beckers, C.J., Joiner, K.A. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  21. Role of anions in parathyroid hormone release from dispersed bovine parathyroid cells. Brown, E.M., Pazoles, C.J., Creutz, C.E., Aurbach, G.D., Pollard, H.B. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  22. Chloride dependence of pH modulation by beta-adrenergic agonist in rat cardiomyocytes. Désilets, M., Pucéat, M., Vassort, G. Circ. Res. (1994) [Pubmed]
  23. Tubular cell apoptosis and cidofovir-induced acute renal failure. Ortiz, A., Justo, P., Sanz, A., Melero, R., Caramelo, C., Guerrero, M.F., Strutz, F., Müller, G., Barat, A., Egido, J. Antivir. Ther. (Lond.) (2005) [Pubmed]
  24. A prelysosomal compartment sequesters membrane-impermeant fluorescent dyes from the cytoplasmic matrix of J774 macrophages. Steinberg, T.H., Swanson, J.A., Silverstein, S.C. J. Cell Biol. (1988) [Pubmed]
  25. Leukotriene C4 uses a probenecid-sensitive export carrier that does not recognize leukotriene B4. Lam, B.K., Xu, K., Atkins, M.B., Austen, K.F. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  26. Dopamine and serotonin metabolism in neuropsychiatrically disturbed children. CSF homovanillic acid and 5-hydroxyindoleacetic acid. Cohen, D.J., Caparulo, B.K., Shaywitz, B.A., Bowers, M.B. Arch. Gen. Psychiatry (1977) [Pubmed]
  27. Simultaneous activity of MRP1 and Pgp is correlated with in vitro resistance to daunorubicin and with in vivo resistance in adult acute myeloid leukemia. Legrand, O., Simonin, G., Beauchamp-Nicoud, A., Zittoun, R., Marie, J.P. Blood (1999) [Pubmed]
  28. Interaction of probenecid with methotrexate transport and release in the isolated rat hepatocyte in suspension. Gewirtz, D.A., Plotkin, J.H., Randolph, J.K. Cancer Res. (1984) [Pubmed]
  29. Glutathione-dependent biotransformation of the alkylating drug thiotepa and transport of its metabolite monoglutathionylthiotepa in human MCF-7 breast cancer cells. Cnubben, N.H., Rommens, A.J., Oudshoorn, M.J., Van Bladeren, P.J. Cancer Res. (1998) [Pubmed]
  30. Hydroxyl/bile acid exchange. A new mechanism for the uphill transport of cholate by basolateral liver plasma membrane vesicles. Blitzer, B.L., Terzakis, C., Scott, K.A. J. Biol. Chem. (1986) [Pubmed]
  31. ATP binding cassette multidrug transporters limit the anti-HIV activity of zidovudine and indinavir in infected human macrophages. Jorajuria, S., Dereuddre-Bosquet, N., Becher, F., Martin, S., Porcheray, F., Garrigues, A., Mabondzo, A., Benech, H., Grassi, J., Orlowski, S., Dormont, D., Clayette, P. Antivir. Ther. (Lond.) (2004) [Pubmed]
  32. MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. Huisman, M.T., Chhatta, A.A., van Tellingen, O., Beijnen, J.H., Schinkel, A.H. Int. J. Cancer (2005) [Pubmed]
  33. Function of the ABC transporters, P-glycoprotein, multidrug resistance protein and breast cancer resistance protein, in minimal residual disease in acute myeloid leukemia. van der Pol, M.A., Broxterman, H.J., Pater, J.M., Feller, N., van der Maas, M., Weijers, G.W., Scheffer, G.L., Allen, J.D., Scheper, R.J., van Loevezijn, A., Ossenkoppele, G.J., Schuurhuis, G.J. Haematologica (2003) [Pubmed]
  34. Probenecid reverses multidrug resistance in multidrug resistance-associated protein-overexpressing HL60/AR and H69/AR cells but not in P-glycoprotein-overexpressing HL60/Tax and P388/ADR cells. Gollapudi, S., Kim, C.H., Tran, B.N., Sangha, S., Gupta, S. Cancer Chemother. Pharmacol. (1997) [Pubmed]
  35. Inhibition of oat3-mediated renal uptake as a mechanism for drug-drug interaction between fexofenadine and probenecid. Tahara, H., Kusuhara, H., Maeda, K., Koepsell, H., Fuse, E., Sugiyama, Y. Drug Metab. Dispos. (2006) [Pubmed]
  36. Acquired resistance to chloroquine in human CEM T cells is mediated by multidrug resistance-associated protein 1 and provokes high levels of cross-resistance to glucocorticoids. Oerlemans, R., van der Heijden, J., Vink, J., Dijkmans, B.A., Kaspers, G.J., Lems, W.F., Scheffer, G.L., Ifergan, I., Scheper, R.J., Cloos, J., Assaraf, Y.G., Jansen, G. Arthritis Rheum. (2006) [Pubmed]
  37. Treatment of early Lyme disease. Massarotti, E.M., Luger, S.W., Rahn, D.W., Messner, R.P., Wong, J.B., Johnson, R.C., Steere, A.C. Am. J. Med. (1992) [Pubmed]
  38. Assessment of active transport of HIV protease inhibitors in various cell lines and the in vitro blood--brain barrier. van der Sandt, I.C., Vos, C.M., Nabulsi, L., Blom-Roosemalen, M.C., Voorwinden, H.H., de Boer, A.G., Breimer, D.D. AIDS (2001) [Pubmed]
  39. Clearance of 3-methoxy-4-hydroxyphenylglycol from the cerebrospinal fluid. Wolfson, L.I., Escriva, A. Neurology (1976) [Pubmed]
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