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Chemical Compound Review

CALCIUM OXALATE     calcium ethanedioate

Synonyms: AG-E-77987, AG-F-97941, CHEBI:60579, AC1L1OTQ, CTK3J2056, ...
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Disease relevance of oxalic acid


Psychiatry related information on oxalic acid


High impact information on oxalic acid


Chemical compound and disease context of oxalic acid


Biological context of oxalic acid

  • In the presence of the inhibitor, the kinetics of calcium oxalate monohydrate crystal growth inhibitor showed that the macromolecule binds to the crystal surface according to a Langmuir adsorption isotherm with a dissociation constant, Kd = 5.3 X 10(-7) M [15].
  • A low level of endogenous casein kinase II activity was found in crude preparations of cardiac SR but did not co-purify with SR vesicles after calcium oxalate loading, suggesting that casein kinase II phosphorylation in vivo occurs at a site other than the SR [16].
  • 0. Ca2+ ions, which were transported into vesicles under conditions resulting in low coupling ratios, were retained as the calcium oxalate precipitate, following complete hydrolysis of substrate [17].
  • Once present on the cell surface, calcium oxalate monohydrate, calcium oxalate dihydrate, and hydroxyapatite crystals are quickly internalized by renal cells; alterations in gene expression and initiation of proliferation may then ensue [18].
  • It is characterized by an elevated anion gap metabolic acidosis, osmolal gap, calcium oxalate crystals in the urine, and a well-defined clinical picture [19].

Anatomical context of oxalic acid


Associations of oxalic acid with other chemical compounds


Gene context of oxalic acid


Analytical, diagnostic and therapeutic context of oxalic acid

  • Under the same conditions of dietary and fluid intake the urine samples of the patients with stone formation were more supersaturated with calcium oxalate (P less than 0.001) and had lower concentrations of protective inhibitors of crystallization (P less than 0.001) than those of the controls [9].
  • Arthritis associated with calcium oxalate crystals in an anephric patient treated with peritoneal dialysis [10].
  • Second, the concentration product ratio (CPR), the ratio of the measured calcium oxalate concentration product before to that after incubation of the sample with calcium oxalate monohydrate crystal, was measured in seven uremic and seven normal serum ultrafiltrates [32].
  • We describe 4 patients who, during the course of long-term hemodialysis, developed calcium oxalate crystal deposits in the synovium and skin [33].
  • Using ryanodine-mediated calcium oxalate loading of SR vesicles followed by density gradient centrifugation, we have shown that calnexin is a bona fide SR protein and an integral constituent of both junctional and free SR vesicles [34].


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  2. Calcium oxalate urolithiasis in mice lacking anion transporter Slc26a6. Jiang, Z., Asplin, J.R., Evan, A.P., Rajendran, V.M., Velazquez, H., Nottoli, T.P., Binder, H.J., Aronson, P.S. Nat. Genet. (2006) [Pubmed]
  3. Absence of Oxalobacter formigenes in cystic fibrosis patients: a risk factor for hyperoxaluria. Sidhu, H., Hoppe, B., Hesse, A., Tenbrock, K., Brömme, S., Rietschel, E., Peck, A.B. Lancet (1998) [Pubmed]
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  7. A key stone cop regulates oxalate homeostasis. Kleta, R. Nat. Genet. (2006) [Pubmed]
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  9. Saturation-inhibition index as a measure of the risk of calcium oxalate stone formation in the urinary tract. Robertson, W.G., Peacock, M., Marshall, R.W., Marshall, D.H., Nordin, B.E. N. Engl. J. Med. (1976) [Pubmed]
  10. Arthritis associated with calcium oxalate crystals in an anephric patient treated with peritoneal dialysis. Rosenthal, A., Ryan, L.M., McCarty, D.J. JAMA (1988) [Pubmed]
  11. Isolation from human calcium oxalate renal stones of nephrocalcin, a glycoprotein inhibitor of calcium oxalate crystal growth. Evidence that nephrocalcin from patients with calcium oxalate nephrolithiasis is deficient in gamma-carboxyglutamic acid. Nakagawa, Y., Ahmed, M., Hall, S.L., Deganello, S., Coe, F.L. J. Clin. Invest. (1987) [Pubmed]
  12. The presence of protein-bound gamma-carboxyglutamic acid in calcium-containing renal calculi. Lian, J.B., Prien, E.L., Glimcher, M.J., Gallop, P.M. J. Clin. Invest. (1977) [Pubmed]
  13. Piridoxilate-associated calcium oxalate urinary calculi: a new metabolic drug-induced nephrolithiasis. Daudon, M., Reveillaud, R.J., Jungers, P. Lancet (1985) [Pubmed]
  14. Body size and risk of kidney stones. Curhan, G.C., Willett, W.C., Rimm, E.B., Speizer, F.E., Stampfer, M.J. J. Am. Soc. Nephrol. (1998) [Pubmed]
  15. Purification and characterization of the principal inhibitor of calcium oxalate monohydrate crystal growth in human urine. Nakagawa, Y., Abram, V., Kézdy, F.J., Kaiser, E.T., Coe, F.L. J. Biol. Chem. (1983) [Pubmed]
  16. GRP94 resides within cardiac sarcoplasmic reticulum vesicles and is phosphorylated by casein kinase II. Cala, S.E., Jones, L.R. J. Biol. Chem. (1994) [Pubmed]
  17. Effects of pH, temperature, and calcium concentration on the stoichiometry of the calcium pump of sarcoplasmic reticulum. Meltzer, S., Berman, M.C. J. Biol. Chem. (1984) [Pubmed]
  18. Nucleation, adhesion, and internalization of calcium-containing urinary crystals by renal cells. Lieske, J.C., Deganello, S. J. Am. Soc. Nephrol. (1999) [Pubmed]
  19. Acidosis and coma after hemodialysis. Taylor, R., Bower, J., Salem, M.M. J. Am. Soc. Nephrol. (1997) [Pubmed]
  20. Microsomal T system: a stereological analysis of purified microsomes derived from normal and dystrophic skeletal muscle. Scales, D.J., Sabbadini, R.A. J. Cell Biol. (1979) [Pubmed]
  21. Uptake of calcium by the endoplasmic reticulum of the frog photoreceptor. Ungar, F., Piscopo, I., Letizia, J., Holtzman, E. J. Cell Biol. (1984) [Pubmed]
  22. Primary role of sarcoplasmic reticulum in phasic contractile activation of cardiac myocytes with shunted myolemma. Chiesi, M., Ho, M.M., Inesi, G., Somlyo, A.V., Somlyo, A.P. J. Cell Biol. (1981) [Pubmed]
  23. Cloning and preliminary characterization of a calcium-binding protein closely related to nucleolin on the apical surface of inner medullary collecting duct cells. Sorokina, E.A., Kleinman, J.G. J. Biol. Chem. (1999) [Pubmed]
  24. Inhibition by citrate of spontaneous precipitation of calcium oxalate in vitro. Nicar, M.J., Hill, K., Pak, C.Y. J. Bone Miner. Res. (1987) [Pubmed]
  25. Temporal changes in mRNA expression for bikunin in the kidneys of rats during calcium oxalate nephrolithiasis. Iida, S., Peck, A.B., Johnson-Tardieu, J., Moriyama, M., Glenton, P.A., Byer, K.J., Khan, S.R. J. Am. Soc. Nephrol. (1999) [Pubmed]
  26. Dissolved urate salts out calcium oxalate in undiluted human urine in vitro: implications for calcium oxalate stone genesis. Grover, P.K., Marshall, V.R., Ryall, R.L. Chem. Biol. (2003) [Pubmed]
  27. Increased expression of monocyte chemoattractant protein-1 (MCP-1) by renal epithelial cells in culture on exposure to calcium oxalate, phosphate and uric acid crystals. Umekawa, T., Chegini, N., Khan, S.R. Nephrol. Dial. Transplant. (2003) [Pubmed]
  28. The association of androgen- and oestrogen-receptor gene polymorphisms with urolithiasis in men. Chen, W.C., Wu, H.C., Lin, W.C., Wu, M.C., Hsu, C.D., Tsai, F.J. BJU international. (2001) [Pubmed]
  29. Crystal-induced inflammation of the kidneys: results from human studies, animal models, and tissue-culture studies. Khan, S.R. Clin. Exp. Nephrol. (2004) [Pubmed]
  30. Vascular endothelial growth factor gene polymorphism is associated with calcium oxalate stone disease. Chen, W.C., Chen, H.Y., Wu, H.C., Wu, M.C., Hsu, C.D., Tsai, F.J. Urol. Res. (2003) [Pubmed]
  31. Arginine form of p21 gene codon 31 is less prominent in patients with calcium oxalate stone. Chen, W.C., Lu, H.F., Chen, H.Y., Hsu, C.D., Tsai, F.J. Urol. Res. (2001) [Pubmed]
  32. Evidence that serum calcium oxalate supersaturation is a consequence of oxalate retention in patients with chronic renal failure. Worcester, E.M., Nakagawa, Y., Bushinsky, D.A., Coe, F.L. J. Clin. Invest. (1986) [Pubmed]
  33. Arthropathy and cutaneous calcinosis in hemodialysis oxalosis. Reginato, A.J., Ferreiro Seoane, J.L., Barbazan Alvarez, C., Mitja Piferrer, J., Vidal Meijon, L., Pascual Turon, R., Vasconez, F., Rivera, E.R., Clayburne, G., Rothfuss, S. Arthritis Rheum. (1986) [Pubmed]
  34. Purification of a 90-kDa protein (Band VII) from cardiac sarcoplasmic reticulum. Identification as calnexin and localization of casein kinase II phosphorylation sites. Cala, S.E., Ulbright, C., Kelley, J.S., Jones, L.R. J. Biol. Chem. (1993) [Pubmed]
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