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Chemical Compound Review

hippurate     2-benzamidoethanoic acid

Synonyms: Hippursaeure, Benzoylglycine, CHEMBL461, Hippuric acid, SureCN7486, ...
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Disease relevance of Benzoylglycine


Psychiatry related information on Benzoylglycine

  • These same conditions provided for the loading of variable amounts of hippurate as a function of reaction time; conjugates were synthesized with 9.6 mol hippurate.mol ConA-1 [6].

High impact information on Benzoylglycine

  • In normal subjects, the FSR for plasma fibronectin using 15N enrichment into urinary hippurate was 35.35 +/- 1.46%/d, whereas the Js/V was 4.45 +/- 0.19 micrograms/ml plasma per h [7].
  • Among all the compounds identified, only hippuric acid, eluted in the fractions of the second group, was capable of inhibiting the uptake of urate and para-aminohippurate in vitro [8].
  • In isolated liver mitochondria, hippurate production from benzoate in the presence of saturating glycine concentrations was reduced in BDL rats by 36% with L-glutamate as a source for ATP, by 21% in the presence of succinate, and by 31% in the presence of ATP plus oligomycine [9].
  • A carboxypeptidase activity that digested angiotensin I to des-Leu-angiotensin I, Ile-His-Pro-Phe to Ile-His-Pro and Phe, and hippuryl-L-phenylalanine to hippuric acid and Phe was detected in the granules of these NK cells [10].
  • METHODS: Metabolic control, clearance of inulin and para-amino hippuric acid, 24 h ambulatory blood pressure and renal biopsies were studied in 41 patients who were 17.8 +/- 0.5 (SEM) years of age and 10.7 +/- 0.5 years after onset of diabetes [11].

Chemical compound and disease context of Benzoylglycine


Biological context of Benzoylglycine


Anatomical context of Benzoylglycine

  • The activities of benzoyl-CoA synthase and benzoyl-CoA:glycine N-acyltransferase were reduced by approximately 60%, and the coenzyme A content by 50% in hepatic mitochondria from cirrhotic rats, explaining impaired hippurate formation [22].
  • Methenamine hippurate in urinary tract infections in children: prophylaxis, treatment and side effects [23].
  • This organism had spiral morphology, with single amphitrichous flagella, and was negative for hippurate hydrolysis, production of urease, and reduction of nitrate [24].
  • Rather, the value of EK(mi) exceeded EK(pmi) because of the ratio of efflux clearances at the basolateral and luminal membranes for hippurate [corrected] was less than 26.089, a value determined by the GFR, plasma renal flow, and the unbound fraction of hippurate of the system that would render E(mi) to equal E(pmi) in the system [25].
  • The flow rate of blood past the portal vein was determined by infusion of P-amino hippuric acid into the ileocolic vein [26].

Associations of Benzoylglycine with other chemical compounds


Gene context of Benzoylglycine

  • The assay involved quantitative conversion of proCPU to active CPU by thrombin-thrombomodulin, a very efficient activator of proCPU, followed by determination of the enzymatic activity of CPU with the substrate hippuryl-L-arginine, using an HPLC-assisted determination of the released hippuric acid [31].
  • In addition, a negative relation was observed between hippuric acid and serum DBH, preceding and following vacation (Rho = -0.46, p = 0.05; Rho = -0.51, p = 0.03) [32].
  • Distribution of urinary hippuric acid concentrations by ALDH2 genotype [33].
  • A hippurate-negative variant of Campylobacter jejuni with a high level of groEL sequence similarity to both C. jejuni (96%) and C. coli (94%) gave a unique AluI profile and an ApoI profile identical to those of other C. jejuni strains [34].
  • As biomarker of exposure, we obtained data on hippuric acid (HA), the main metabolite of toluene in urine, and DNA damage detected by the Comet assay in blood cells [35].

Analytical, diagnostic and therapeutic context of Benzoylglycine


  1. Glue-sniffing and distal renal tubular acidosis: sticking to the facts. Carlisle, E.J., Donnelly, S.M., Vasuvattakul, S., Kamel, K.S., Tobe, S., Halperin, M.L. J. Am. Soc. Nephrol. (1991) [Pubmed]
  2. Clinical evaluation of patients with hypertension and exercise-induced renal dysfunction. Clorius, J.H., Mann, J., Schmidlin, P., Strauss, L.G., Saur, T., Irngartinger, G. Hypertension (1987) [Pubmed]
  3. Angiotensin converting enzyme inhibition improves diagnostic procedures for renovascular hypertension in dogs. Jonker, G.J., de Zeeuw, D., Huisman, R.M., Piers, D.B., Beekhuis, H., van der Hem, G.K. Hypertension (1988) [Pubmed]
  4. Macrolide resistance in Campylobacter jejuni and Campylobacter coli: molecular mechanism and stability of the resistance phenotype. Gibreel, A., Kos, V.N., Keelan, M., Trieber, C.A., Levesque, S., Michaud, S., Taylor, D.E. Antimicrob. Agents Chemother. (2005) [Pubmed]
  5. Technetium-99m-MAG3 clearance as a parameter of effective renal plasma flow in patients with proteinuria and lowered serum albumin levels. Kengen, R.A., Meijer, S., Beekhuis, H., Piers, D.A. J. Nucl. Med. (1991) [Pubmed]
  6. Carbodiimide-mediated conjugation of hippuric acid to concanavalin A: retention of ligand binding and hemagglutinating activities. Preston, J.F., Hencin, R.S. Biochem. Cell Biol. (1986) [Pubmed]
  7. Plasma fibronectin synthesis in normal and injured humans as determined by stable isotope incorporation. Thompson, C., Blumenstock, F.A., Saba, T.M., Feustel, P.J., Kaplan, J.E., Fortune, J.B., Hough, L., Gray, V. J. Clin. Invest. (1989) [Pubmed]
  8. Uricosuric agents in uremic sera. Identification of indoxyl sulfata and hippuric acid. Boumendil-Podevin, E.F., Podevin, R.A., Richet, G. J. Clin. Invest. (1975) [Pubmed]
  9. Benzoic acid metabolism reflects hepatic mitochondrial function in rats with long-term extrahepatic cholestasis. Krähenbühl, L., Reichen, J., Talos, C., Krähenbühl, S. Hepatology (1997) [Pubmed]
  10. Identification of carboxypeptidase and tryptic esterase activities that are complexed to proteoglycans in the secretory granules of human cloned natural killer cells. Kamada, M.M., Michon, J., Ritz, J., Holldack, J., Serafin, W.E., Austen, K.F., MacDermott, R.P., Stevens, R.L. J. Immunol. (1989) [Pubmed]
  11. Ambulatory blood pressure and heart rate in relation to kidney structure and metabolic control in adolescents with Type I diabetes. Torbjörnsdotter, T.B., Jaremko, G.A., Berg, U.B. Diabetologia (2001) [Pubmed]
  12. Differential renal function in unilateral renal injury: possible effects of radiopharmaceutical choice. Taylor, A., Lallone, R. J. Nucl. Med. (1985) [Pubmed]
  13. Diagnostic use of angiotensin converting enzyme inhibitors in radioisotope evaluation of unilateral renal artery stenosis. Kremer Hovinga, T.K., de Jong, P.E., Piers, D.A., Beekhuis, H., van der Hem, G.K., de Zeeuw, D. J. Nucl. Med. (1989) [Pubmed]
  14. Protein-induced glomerular hyperfiltration: role of hormonal factors. Krishna, G.G., Newell, G., Miller, E., Heeger, P., Smith, R., Polansky, M., Kapoor, S., Hoeldtke, R. Kidney Int. (1988) [Pubmed]
  15. Effect of pantothenic acid on hippurate formation in sodium benzoate-treated HepG2 cells. Palekar, A. Pediatr. Res. (2000) [Pubmed]
  16. Characterization of freshly isolated Campylobacter coli strains and suitability of selective media for their growth. Ng, L.K., Taylor, D.E., Stiles, M.E. J. Clin. Microbiol. (1988) [Pubmed]
  17. Renal and hemodynamic effects of isradipine in essential hypertension. Persson, B., Andersson, O.K., Wysocki, M., Hedner, T., Aurell, M. Am. J. Med. (1989) [Pubmed]
  18. Kidney morphological changes in relation to long-term renal function and metabolic control in adolescents with IDDM. Berg, U.B., Torbjörnsdotter, T.B., Jaremko, G., Thalme, B. Diabetologia (1998) [Pubmed]
  19. The serotype and biotype distribution of clinical isolates of Campylobacter jejuni and Campylobacter coli over a three-year period. Karmali, M.A., Penner, J.L., Fleming, P.C., Williams, A., Hennessy, J.N. J. Infect. Dis. (1983) [Pubmed]
  20. Technetium-99m-labeled p-aminohippuric acid analog: a new renal agent: concise communication. Chervu, L.R., Sundoro, B.M., Blaufox, M.D. J. Nucl. Med. (1984) [Pubmed]
  21. Increased tubular organic ion clearance following chronic ACE inhibition in patients with type 1 diabetes. Thomas, M.C., Jerums, G., Tsalamandris, C., Macisaac, R., Panagiotopoulos, S., Cooper, M.E. Kidney Int. (2005) [Pubmed]
  22. Relationship between hepatic mitochondrial functions in vivo and in vitro in rats with carbon tetrachloride-induced liver cirrhosis. Krähenbühl, L., Ledermann, M., Lang, C., Krähenbühl, S. J. Hepatol. (2000) [Pubmed]
  23. Methenamine hippurate in urinary tract infections in children: prophylaxis, treatment and side effects. Elo, J., Sarna, S., Ahava, K., Lepo, A. J. Antimicrob. Chemother. (1978) [Pubmed]
  24. An uncommon Helicobacter isolate from blood: evidence of a group of Helicobacter spp. pathogenic in AIDS patients. Weir, S.C., Gibert, C.L., Gordin, F.M., Fischer, S.H., Gill, V.J. J. Clin. Microbiol. (1999) [Pubmed]
  25. Differences in excretion of hippurate, as a metabolite of benzoate and as an administered species, in the single-pass isolated perfused rat kidney explained. Geng, W., Pang, K.S. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  26. A surgical model for determination of true absorption and biliary excretion of manganese in conscious swine fed commercial diets. Finley, J.W., Caton, J.S., Zhou, Z., Davison, K.L. J. Nutr. (1997) [Pubmed]
  27. A furan fatty acid and indoxyl sulfate are the putative inhibitors of thyroxine hepatocyte transport in uremia. Lim, C.F., Bernard, B.F., de Jong, M., Docter, R., Krenning, E.P., Hennemann, G. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  28. A difference in the incorporation of 14C into hippurate glycine from DL-(2-14C)-glutamate and DL-(5-14C)glutamate in guinea pigs. Rowsell, K.V., Ali, T.A. Biochem. J. (1975) [Pubmed]
  29. Studies on dialysate mixing in the Genius single-pass batch system for hemodialysis therapy. Dhondt, A.W., Vanholder, R.C., De Smet, R.V., Claus, S.A., Waterloos, M.A., Glorieux, G.L., Delanghe, J.R., Lameire, N.H. Kidney Int. (2003) [Pubmed]
  30. Movement of fluorescein and its glucuronide across retinal pigment epithelium-choroid. Koyano, S., Araie, M., Eguchi, S. Invest. Ophthalmol. Vis. Sci. (1993) [Pubmed]
  31. Assay of procarboxypeptidase U, a novel determinant of the fibrinolytic cascade, in human plasma. Schatteman, K.A., Goossens, F.J., Scharpé, S.S., Neels, H.M., Hendriks, D.F. Clin. Chem. (1999) [Pubmed]
  32. Pilot study of peripheral markers of catecholaminergic systems among workers occupationally exposed to toluene. Smargiassi, A., Mutti, A., Bergamaschi, E., Bélanger, S., Truchon, G., Mergler, D. Neurotoxicology (1996) [Pubmed]
  33. Distribution of urinary hippuric acid concentrations by ALDH2 genotype. Kawamoto, T., Murata, K., Koga, M., Hattori, Y., Kodama, Y. Occupational and environmental medicine. (1994) [Pubmed]
  34. Phylogenetic analysis and PCR-restriction fragment length polymorphism identification of Campylobacter species based on partial groEL gene sequences. Kärenlampi, R.I., Tolvanen, T.P., Hänninen, M.L. J. Clin. Microbiol. (2004) [Pubmed]
  35. Evaluation of genetic damage in Brazilian footwear-workers: Biomarkers of exposure, effect, and susceptibility. Heuser, V.D., Erdtmann, B., Kvitko, K., Rohr, P., da Silva, J. Toxicology (2007) [Pubmed]
  36. Diagnosis of impaired renal function after kidney transplantation using renal scintigraphy, renal plasma flow and urinary excretion of hippurate. Diethelm, A.G., Dubovsky, E.V., Whelchel, J.D., Hartley, M.W., Tauxe, W.N. Ann. Surg. (1980) [Pubmed]
  37. Nondipping and its relation to glomerulopathy and hyperfiltration in adolescents with type 1 diabetes. Torbjörnsdotter, T.B., Jaremko, G.A., Berg, U.B. Diabetes Care (2004) [Pubmed]
  38. Predictive value of exercise renography for presurgical evaluation of nephrogenic hypertension. Clorius, J.H., Allenberg, J., Hupp, T., Strauss, L.G., Schmidlin, P., Irngartinger, G., Wagner, R., Mukhopadhyay, C. Hypertension (1987) [Pubmed]
  39. Effect of diet on serum accumulation and renal excretion of aryl acids and secretory activity in normal and uremic man. Cathcart-Rake, W., Porter, R., Whittier, F., Stein, P., Carey, M., Grantham, J. Am. J. Clin. Nutr. (1975) [Pubmed]
  40. A liquid chromatography-assisted assay for angiotensin-converting enzyme (peptidyl dipeptidase) in serum. Chiknas, S.G. Clin. Chem. (1979) [Pubmed]
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