Abstract
The ideal drug for the treatment of hyperuricemia would be one which reduces uric acid synthesis without interfering with important anabolic pathways or normal regulatory functions. In theory, uric acid production may be inhibited at a number of different enzymatic steps, either those involved in the de novo pathway of purine biosynthesis or those concerned with the final stages of purine catabolism. Compounds such as azaserine and diazo-oxo-norleucine which block the early steps of purine biosynthesis reduce uric acid synthesis but also interfere with nucleic acid synthesis and are therefore cytotoxic (Grayzel et al., 1960; Zuckerman et al., 1959). Inhibition of xanthine oxidase, on the other hand, has proven to be a clinically safe and effective method of reducing uric acid formation.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Ablin, A., Stephens, B.G., Hirata, T., Wilson, K., Williams, H.E.: Nephropathy, xanthinuria, and orotic aciduria complicating Burkitt’s lymphoma treated with chemotherapy and allopurinol. Metabolism 21, 771–778 (1972)
Alberts, D.S., Van Dallen Wetters, T.: Allopurinol potentiates cyclophosphamide antileukemic activity. Proc. Amer. Ass. Cancer Res. 16, 84 (1975)
Alexander, J.A., Wheeler, G.P., Hill, D.D., Morris, H.P.: Effects of 4-hydroxypyrazolo(3,4-d)pyrimidine upon the catabolism of purines by various tissues of the rat and upon the rate of growth of Morris 5123-C hepatoma. Biochem. Pharmacol. 15, 881–889 (1966)
Alken, C.E., May, P., Braun, J.S.: Analysis of treatment results in uric acid lithiasis with and without hyperuricemia. Advanc. exp. Med. Biol. 41B, 535–540 (1974)
Auscher, C., Mercier, N., Pasquier, C.: Allopurinol and thiopurinol: effect in vivo on urinary oxypurine excretion and rate of synthesis of their ribonucleotides in different enzymatic deficiencies. Advanc. exp. Med. Biol. 41B, 657–662 (1974a)
Auscher, C., Pasquier, C., Mercier, N., Delbarre, F.: Urinary excretion of 6-hydroxylated metabolite and oxypurines in a xanthinuric man given allopurinol or thiopurinol. Advanc. exp. Med. Biol. 41B, 663–667 (1974)
Ayvazian, J.H.: Xanthinuria and hemochromatosis. New Engl. J. Med. 270, 18–22 (1964)
Badawy, A.A.-B., Evans, M.: The mechanism of rat liver tryptophan pyrrolase activity by 4-hydroxypyrazolo[3,4-d]pyrimidine (allopurinol). Biochem. J. 133, 585–591 (1973)
Badawy, A.A., Evans, M.: Tryptophan plus a pyrrolase inhibitor for depression? Lancet 1974 II, 1209–1210
Bagley, C.M., Jr., Bostick, F.W., De Vita, V.T., Jr.: Clinical pharmacology of cyclophosphamide. Cancer Res. 33, 226–233 (1973)
Baker, C. H.: Protection against irreversible haemorrhagic shock by allopurinol. Proc. Soc. exp. Biol. (N.Y.) 141, 694–698 (1972)
Balis, M.E., Krakoff, I.H., Berman, P.H., Dancis, J.: Urinary metabolites in congenital hyperuricosuria. Science 156, 1122–1123 (1967)
Band, P.R., Silverberg, D.S., Henderson, J.F, Ulan, R.A., Wensel, R.H., Bannerjee, T.K, Little, A.S.: Xanthine nephropathy in a patient with lymphosarcoma treated with allopurinol. New Engl. J. Med. 283, 354–357 (1970)
Beardmore, T.D., Cashman, J.S., Kelley, W.N.: Mechanism of allopurinol-mediated increase in cultured human fibroblasts. J. clin. Invest. 51, 1823–1832 (1972)
Beardmore, T.D., Kelley, W.N.: Mechanism of allopurinol-mediated inhibition of pyrimidine biosynthesis. J. Lab. clin. Med. 78, 696–704 (1971)
Becker, M.A., Argubright, K.F., Fox, R.M., Seegmiller, J.E.: Oxipurinol-associated inhibition of pyrimidine synthesis in human lymphoblasts. Molec. Pharmacol. 10, 657–668 (1974)
Becking, G.C., Johnson, W.J.: The inhibition of tryptophan pyrrolase by allopurinol, an inhibitor of xanthine oxidase. Canad. J. Biochem. 45, 1667–1672 (1967)
Becking, G.C., Johnson, W.J.: Pyrazolo-and triazolopyrimidines as inhibitors of tryptophan pyrrolase. Life Sci. 8II, 843–851 (1969)
Boston Collaborative Drug Surveillance Program: Excess of ampicillin rashes associated with allopurinol or hyperuricemia. New Engl. J. Med. 286, 505–507 (1972)
Boston Collaborative Drug Surveillance Program: Allopurinol and cytotoxic drugs. Interaction in relation to bone marrow depression. J. Amer. med. Ass. 227, 1036–1040 (1974)
Boyett, J.D., Vogler, W.R., Furtado, V. de P., Schmidt, F.H.: Allopurinol and iron metabolism in man. Blood 32, 460–468 (1968)
Brown, G.K., Fox, R.M., O’Sullivan, W.J.: Alteration of quaternary structural behavior of an hepatic orotate phosphoribosyltransferase-orotidine-5′-phosphate decarboxylase complex in rats following allopurinol therapy. Biochem. Pharmacol. 21, 2469–2477 (1972)
Brown, G.K., Fox, R.M., O’Sullivan, W.J.: Interconversion of different molecular weight forms of human erythrocyte orotidylate decarboxylase. J. biol. Chem. 250, 7352–7358 (1975)
Buchanan, J.M., Flaks, J.G., Hartman, S.C., Levenberg, B., Lukens, L.N, Warren, L.: The enzymatic synthesis of inosinic acid de novo. In: Wolstenholme, G.E.W., O’Connor, C.M. (Eds.): Chemistry and Biology of Purines, Ciba Foundation Symposium, May 1956, pp. 233–252. Boston: Little Brown 1957
Burroughs Wellcome Co.: Unpublished reports
Byers, S.O.: Xanthine oxidase studies. J. Amer, pharm. Ass. sci. Ed. 41, 611–613 (1952)
Cartier, P.H., Hamet, M.: Mechanism of antiuric action of 4-oxy- and 4-thiopyrazolopyrimidines. Biochem. Pharmacol. 22, 3061–3075 (1973)
Chalmers, R.A., Krorner, H., Scott, J.T., Watts, R.W.E.: A comparative study of the xanthine oxidase inhibitors allopurinol and oxipurinol in man. Clin. Sci. 35, 353–362 (1968)
Chalmers, R.A., Parker, R., Simmonds, H.A., Snedden, W., Watts, R.W.E.: The conversion of 4-hydroxypyrazolo[3,4-d]pyrimidine (allopurinol) into 4,6-dihydroxypyrazolo[3,4-d]pyrimidine (oxipurinol) in vivo in the absence of xanthine-oxygen oxido reductase. Biochem. J. 112, 527–532(1969)
Chatterjee, S.N., Berne, T.V.: Protective effect of allopurinol in renal ischemia. Amer. J. Surg. 131, 658–659(1976)
Chytil, F.: Activation of liver tryptophan oxygenase by adenosine 3’,5’-phosphate and by other purine derivatives. J. biol. Chem. 243, 893–899 (1968)
Clifford, A., Riumallo, J.A., Baliga, B.S., Munro, H.N., Brown, P.R.: Liver nucleotide metabolism in relation to amino acid supply. Biochim. biophys. (Amst.) Acta 277, 443–458 (1972)
Coe, F. L., Kavalach, A.G.: Hypercalciuria and hyperuricosuria in patients with calcium nephrolithiasis. New Engl. J. Med. 291, 1344–1350 (1974)
Coe, F.L., Lawton, R.L., Goldstein, R.B., Tembe, V.: Sodium urate accelerates precipitation of calcium oxalate in vitro. Proc. Soc. exp. Biol. (N.Y.) 149, 926–929 (1975)
Coe, F.L., Raiser, L.: Allopurinol treatment of uric acid disorders in calcium stone formers. Lancet 1973 I, 129–131
Coffey, J. J., White, C.A., Lesk, A.B., Rogers, W.I., Serpick, A.A.: Effect of allopurinol on the pharmacokinetics of 6-MP in cancer patients. Cancer Res. 32, 1283–1289 (1972)
Crowell, J.W.: Oxygen transport in the hypotensive state. Fed. Proc. 29, 1848–1853 (1970)
Crowell, J.W., Jones, C.E., Smith, E.E.: Effect of allopurinol on hemorrhagic shock. Amer. J. Physiol. 216, 744–748 (1969)
Cunningham, S.K., Keaveny, T.V., Fitzgerald, P.: Effect of allopurinol on tissue ATP, ADP, and AMP concentrations in renal ischaemia. Brit. J. Surg. 61, 562–565 (1974)
Davis, P.S., Deller, D.J.: Effect of a xanthine oxidase inhibitor (allopurinol) on radio-iron absorption in man. Lancet 1966 II, 470–472
Dean, B.M., Perrett, D., Simmonds, H.A., Grahame, R.: Thiopurinol: comparative enzyme inhibition and protein binding studies with allopurinol, oxipurinol and 6-mercaptopurine. Brit. J. clin. Pharmacol. 1, 119–127 (1974)
Delbarre, F., Auscher, C., DeGery, A., Brouilhet, H., Olivier, J.-L.: Le traitement de la dyspurin-urie goutteuse par la mercapto-pyrazolopyrimidine (M.P.P.: thiopurinol). Presse méd. 76, 2329–2332 (1968)
Delbarre, F., Auscher, C., Thang, K.V., Brouilhet, H., De Gery, A.: Effet de retroaction de certaines pyrazolopyrimidines sur le métabolisme de l’acide urique. CR. Acad. Sci. (Paris) 267, 2231–2234 (1968a)
Delbarre, F., Cartier, P., Auscher, C., De Gery, A., Hamet, M.: Dyspurinies par déficit en hypoxanthine-guanine-phosphoribosyl-transferase. Fréquence et caractères cliniques de l’anenzymose. Presse méd. 78, 729–734 (1970)
De Vries, A., Frank, M.: Prophylaxis of idiopathic and gouty uric acid lithiasis by allopurinol. Urol. int. 22, 505–516 (1967)
De Vries, A., Frank, M., Libermon, U.A., Sperling, O.: Allopurinol in the prophylaxis of uric acid stones. Ann. rheum. Dis. 25, 691–693 (1966)
De Vries, A., Sperling, O.: Recent data on uric acid lithiasis. Adv. Nephrol. 3, 89–116 (1974)
De Wall, R.A., Vasko, K.A., Stanley, E.L., Kezdi, P.: The responses of the ischemic myocardium to allopurinol. Amer. Heart J. 82, 362–370 (1971)
Duggan, D.E., Noll, R.M., Baer, J.E., Novello, F.C., Baldwin, J.J.: 3,5-Disubstituted-1,2,4-triazoles, a new class of xanthine oxidase inhibitor. J. med. Chem. 18, 900–905 (1975)
Edmondson, D., Massey, V., Palmer, G., Beacham, L.M., III, Elion, G.B.: The resolution of active and inactive xanthine oxidase by affinity chromatography. J. biol. Chem. 247, 1597–1604 (1972)
Elion, G. B.: Unpublished
Elion, G.B.: Enzymatic and metabolic studies with allopurinol. Ann. rheum. Dis. 25, 608–614 (1966)
Elion, G.B.: Interaction of anticancer drugs with enzymes. In: Pharmacological Basis of Cancer Chemotherapy, pp. 547–564. Baltimore Maryland: Williams and Wilkins Co. 1975
Elion, G.B., Benezra, F.M., Canellas, I., Carrington, L.O., Hitchings, G.H.: Effects of xanthine oxidase inhibitors on purine catabolism. Israel J. Chem. 6, 787–796 (1968)
Elion, G.B., Bieber, S., Hitchings, G.H.: The fate of 6-mercaptopurine in mice. Ann. N.Y. Acad. Sci. 60, 297–303 (1954)
Elion, G.B., Callahan, S.W., Hitchings, G.H., Rundles, R.W., Laszlo, J.: Experimental, clinical, and metabolic studies of thiopurines. Cancer Chemother. Rep. 16, 197–202 (1962)
Elion, G.B., Callahan, S., Nathan, H., Bieber, S., Rundles, R. W., Hitchings, G.H.: Potentiation by inhibition of drug degradation: 6-substituted purines and xanthine oxidase. Biochem. Pharmacol. 12, 85–93 (1963)
Elion, G.B., Callahan, S., Rundles, R.W., Hitchings, G.H.: Relationship between metabolic fates and antitumor activities of thiopurines. Cancer Res. 23, 1207–1217 (1963a)
Elion, G.B., Hitchings, G.H.: Azathioprine. In: Sartorelli, A.C., Johns, D.G. (Eds.): Handbook of experimental pharmacology, New Series, Vol. 38, Pt. 2, pp. 404–425. Berlin-Heidelberg-New York: Springer 1975
Elion, G.B., Kovensky, A., Hitchings, G.H., Metz, E., Rundles, R.W.: Metabolic studies of allopurinol, an inhibitor of xanthine oxidase. Biochem. Pharmacol. 15, 863–880 (1966)
Elion, G.B., Mueller, S., Hitchings, G.H.: Studies on condensed pyrimidine systems XXI. The isolation of synthesis of 6-mercapto-2,8-purinediol (6-thiouric acid). J. Amer. chem. Soc. 81, 3042–3045 (1959)
Elion, G.B., Nelson, D.J.: Ribonucleotides of allopurinol and oxipurinol in rat tissues and their significance in purine metabolism. Advanc. exp. Med. Biol. 41B, 639–652 (1974)
Elion, G.B., Yu, T.-F., Gutman, A.B., Hitchings, G.H.: Renal clearance of oxipurinol, the chief metabolite of allopurinol. Amer. J. Med. 45, 69–77 (1968)
Ellis, C.H., Touw, K.B., Dickerson, S.W.: Some acute hemodynamic effects of large doses of sodium allopurinol in open-chested dogs. Arch. int. Pharmacodyn. Therap. 205, 355–367 (1973)
Emmerson, B.T.: Effect of allopurinol on iron metabolism in man. Ann. rheum. Dis. 25, 700–703 (1966)
Engelman, K., Watts, R.W.E., Klineberg, J.R., Sjoerdsma, A., Seegmiller, J.E.: Clinical, physiological and biochemical studies of a patient with xanthinuria and pheochromocytoma. Amer. J. Med. 37, 839–861 (1964)
Fox, I.H., Kelley, W.N.: Phosphoribosylpyrophosphate in man: biochemical and clinical significance. Ann. intern. Med. 74, 424–433 (1971)
Fox, I.H., Wyngaarden, J.B., Kelley, W.N.: Depletion of erythrocyte phosphoribosylpyrophosphate in man—a newly observed effect of allopurinol. New Engl. J. Med. 283, 117–1182 (1970)
Fox, R.M., Royse-Smith, D., O’Sullivan, W.J.: Orotidinuria induced by allopurinol. Science 168, 861–862(1970)
Fox, R.M., Wood, M.H., O’Sullivan, W.J.: Studies on the coordinate activity and lability of orotidylate phosphoribosyl transferase and decarboxylase in human erythrocytes, and the effects of allopurinol administration. J. clin. Invest. 50, 1050–1060 (1971)
Fyfe, J.A., Miller, R.L., Krenitsky, T.A.: Kinetic properties and inhibition of orotidine 5’-phos-phate decarboxylase. J. biol. Chem. 248, 3801–3809 (1973)
Fyfe, J.A., Nelson, D.J., Hitchings, G.H.: The molecular basis of the effects of allopurinol on pyrimidine metabolism. Adv. exp. Med. Biol. 41B, 621–628 (1974)
Gevirtz, N.R.: Allopurinol and iron metabolism. Lancet 1967 II, 715
Glogner, P.: Metabolism of tolbutamide and cyclamate. Hum. Genet. 9, 230–232 (1970)
Goldfinger, S., Klinenberg, J.R., Seegmiller, J.E.: The renal excretion of oxypurines. J. clin. Invest. 44, 623–628(1965)
Grace, N.D., Greenwald, M.A., Greenberg, M.S.: Effect of allopurinol on iron mobilization. Gastroenterology 59, 103–108 (1970)
Grahame, R., Simmonds, H.A., Cadenhead, A., Dean, B.M.: Metabolic studies of thiopurinol in man and pig. Advanc. exp. Biol. Med. 41B, 597–605 (1974)
Grahame, R., Simmonds, H.A., Cameron, J.S., Cadenhead, A.: Thiopurinol: dose related effect on urinary oxypurine excretion. J. clin. Chem. clin. Biochem. 14, 291 (1976)
Grayzel, A., Seegmiller, J.E., Lane, E.: Suppression of uric acid synthesis in the gouty human by the use of 6-diazo-5-oxo-L-norleucine. J. clin. Invest. 39, 447–454 (1960)
Green, A.R., Curzon, G.: Decrease of 5-hydroxytryptamine in the brain provoked by hydrocortisone and its prevention by allopurinol. Nature (Lond.) 220, 1095–1097 (1968)
Green, R., Levin, N.W., Samassa, D., Charlton, R.W., Bothwell, T.H.: The effect of allopurinol on iron metabolism. S. Afr. med. J. 42, 776–779 (1968)
Green, A.R., Woods, H.F., Joseph, M.H.: Tryptophan metabolism in the isolated perfused liver of the rat: effects of tryptophan concentration, hydrocortisone and allopurinol on tryptophan concentration, hydrocortisone and allopurinol on tryptophan pyrrolase activity and kynurenine formation. Brit. J. Pharmacol. 57, 103–114 (1976)
Greenberg, R.: Discussion. In: Wolstenholme, G.E.W., O’Conner, C.M. (Eds.): Chemistry and Biology of Purines, Ciba Foundation Symposium, May 1956, p. 267. Boston: Little Brown 1957
Greene, M.L., Fujimoto, W.Y., Seegmiller, J.E.: Urinary xanthine stones—a rare complication of allopurinol therapy. New Engl. J. Med. 280, 426–427 (1969)
Grindey, G.B., Moran, R.G.: Effects of allopurinol on the therapeutic efficacy of methotrexate. Cancer Res. 35, 1702–1705 (1975)
Grobner, W., Kelley, W.N.: Effect on allopurinol and its metabolic derivatives on the configuration of human orotate phosphoribosyltransferase and orotidine 5’-phosphate decarboxylase. Biochem. Pharmacol. 24, 379–384 (1975)
Gutman, A.B., Yii, T.-F.: Uric acid nephrolithiasis. Amer. J. Med. 45, 756–779 (1968)
Hamilton, L., Elion, G.B.: The fate of 6-mercaptopurine in man. Ann. N.Y. Acad. Sci. 60, 304–314(1954)
Haskovec, L., Dostal, T., Jirak, R.: The action of allopurinol as an inhibitor of liver tryptophan pyrrolase in depressions. Activ. nerv. sup. (Praha) 14, 131–132 (1972)
Hatfield, D., Wyngaarden, J.B.: 3-ribosylpurines. I. Synthesis (3-ribosyluric acid)5′-phosphate and (3-ribosylxanthine)5′-phosphate by a pyrimidine ribonucleotide pyrophosphorylase of beef erythrocytes. J. biol. Chem. 239, 2580–2586 (1964)
Hatfield, D., Wyngaarden, J.B.: II. Studies on (3-ribosylxanthine)-5′-phosphate and on ribonucleotide derivatives of certain uracil analogues. J. biol. Chem. 239, 2587–2592 (1964a)
Hayes, C.P., Jr., Metz, E.N., Robinson, R.R., Rundles, R.W.: The use of allopurinol (HPP) to control hyperuricemia in patients on chronic intermittent hemodialysis. Trans. Amer. Soc. artif. internal Org. 11, 247–251 (1965)
Hillier, J., Hillier, J.G., Redfern, P.H.: Liver tryptophan pyrrolase activity and metabolism of brain 5-HT in rat. Nature (Lond.) 253, 566–567 (1975)
Hitchings, G.H.: Effects of allopurinol in relation to purine biosynthesis. Ann. rheum. Dis. 25, 601–607(1966)
Hitchings, G.H.: Allopurinol, an inhibitor of xanthine oxidase; physiological and biochemical studies. In: Shugar, D. (Ed.): FEBS Symposium, Biochemical Aspects of Antimetabolites and of Drug Hydroxylation, Vol. 16, pp. 11–22. London-New York: Academic Press 1969
Hitchings, G.H.: Crystals in skeletal muscle. Brit. med. J. 1971 IV, 555 (1971)
Hitchings, G.H.: Indications for control mechanisms in purine and pyrimidine biosynthesis as revealed by studies with inhibitors. In: Advances in enzyme regulation, Vol. 12, pp. 121–129. Oxford: Pergamon 1974
Hitchings, G.H.: Pharmacology of allopurinol. Arthr. and Rheum. 18, 863–870 (1975)
Hitchings, G.H., Elion, G.B.: Mechanisms of action of purine and pyrimidine analogues. In: Brodsky, I., Kahn, S.B., Mover, J.H. (Eds.): Cancer Chemotherapy II, 22nd Hahnemann Symposium, pp. 23–32. New York: Grune and Stratton 1972
Hoenig, V., Brodanonva, M., Strejcek, J., Kordac, V.: Allopurinol and iron metabolism. Lancet 1967 I, 387
Holmes, E.W., Mason, D.H., Goldstein, L.I., Blount, R.E., Kelley, W.N.: Xanthine oxidase deficiency: studies of a previously unreported case. Clin. Chem. 20, 1076–1079 (1974)
Hopkins, R.W., Abraham, J., Simeone, F.A., Damewood, C.A.: Effect of allopurinol on hepatic adenosine nucleotides in hemhorrhagic shock. J. Surg. Res. 19, 381–390 (1975)
Imai, S., Riley, A.L., Berne, R.M.: Effect of ischemia on adenine nucleotides in cardiac and skeletal muscle. Circulat. Res. 15, 443–450 (1964)
Iwata, H., Yamamoto, J., Huh, K.: Sex differences in allopurinol oxidizing enzyme activity in mouse liver supernatant fraction. Biochem. Pharmacol. 23, 1144–1146 (1974)
Iwata, H., Yamamoto, J., Muraki, K., Goda, E.: Sex differences of acute toxicity in rats and mice. In: 1st Symp. on Drug Metabolism and Action, Chiba, Japan, Nov. 1969, pp. 124–129
Jones, C.E., Crowell, J.W., Smith, E.E.: Significance of increased blood uric acid following extensive hemhorrage. Amer. J. Physiol. 214, 1374–1377 (1968)
Julian, J., Chytil, E.: Participation of xanthine oxidase in the activation of liver tryptophan pyrrolase. J. biol. Chem. 245, 1161–1168 (1970)
Kann, H.E, Jr., Wells, J.H., Galleli, J.F., Schein, P.S., Cooney, D.A., Smith, E.R., Seegmiller, J.E., Carbone, P.P.: The development and use of an intravenous preparation of allopurinol. Amer. J. med. Sci. 256, 53–63 (1968)
Kelley, W.N., Beardmore, T.D.: Allopurinol: Alteration in pyrimidine metabolism in man. Both allopurinol and oxypurinol inhibit de novo pyrimidine biosynthesis. Science 169, 388–390 (1970)
Kelley, W.N., Beardmore, T.D., Fox, I.H., Meade, J.C.: Effects of allopurinol and oxipurinol on pyrimidine synthesis in cultured human fibroblasts. Biochem. Pharmacol. 20, 1471–1478 (1971)
Kelley, W.M., Wyngaarden, J.B.: Effects of allopurinol and oxipurinol on purine synthesis in cultured human cells. J. clin. Invest. 49, 602–609 (1970)
Klinenberg, J.R., Goldfinger, S.E., Seegmiller, J.E.: Effectiveness of the xanthine oxidase inhibitor allopurinol in the treatment of gout. Ann. intern. Med. 62, 639–647 (1965)
Kozma, C., Salvador, R.A., Elion, G.B.: Allopurinol and iron storage. Lancet 1967 II, 1040–1041
Kozma, C., Salvador, R.A., Elion, G.B.: Chronic allopurinol administration and iron storage in mice. Life Sci. 7, 341–348 (1968)
Krakoff, I.H., Meyer, R.L.: Prevention of hyperuricemia in leukemia and lymphoma. Use of allopurinol, a xanthine oxidase inhibitor. J. Amer. med. Ass. 193, 89–94 (1965)
Krakoff, I.H., Murphy, M.L.: Hyperuricemia in neoplastic disease in children: prevention with allopurinol, a xanthine oxidase inhibitor. Pediatrics 41, 52–56 (1968)
Krenitsky, T.A.: Purine nucleoside Phosphorylase: kinetics, mechanism, and specificity. Molec. Pharmacol. 3, 526–536 (1967)
Krenitsky, T.A.: Tissue distribution of purine ribosyl and phosphoribosyl-transferase in the Rhesus monkey. Biochim. biophys. Acta (Amst.) 179, 506–509 (1969)
Krenitsky, T.A., Elion, G.B., Henderson, A.M., Hitchings, G.H.: Inhibition of human purine nucleoside Phosphorylase. J. biol. Chem. 243, 2876–2881 (1968)
Krenitsky, T.A., Elion, G.B., Strelitz, R.A., Hitchings, G.H.: Ribonucleosides of allopurinol and oxoallopurinol. J. biol. Chem. 242, 2675–2682 (1967)
Krenitsky, T.A., Mellors, J.W., Barclay, R.K.: Pyrimidine nucleosidases. Their classification and relationship to uric acid ribonucleoside Phosphorylase. J. biol. Chem. 240, 1281–1286 (1965)
Krenitsky, T.A., Neil, S.M., Elion, G.B., Hitchings, G.H.: A comparison of the specificities of xanthine oxidase and aldehyde oxidase. Arch. Biochem. Biophys. 150, 585–599 (1972)
Krenitsky, T.A., Papaioannau, R., Elion, G.B.: Human hypoxanthine phosphoribosyltransferase. I. purification, properties, and specificity. J. biol. Chem. 244, 1263–1270 (1969)
Landgrebe, A.R., Nyhan, W.L., Coleman, M.: Urinary-tract stones resulting from the excretion of oxipurinol. New Engl. J. Med. 292, 626–627 (1975)
Lazarus, H.M., Owens, M.L., Hopfenbeck, A.: Allopurinol protection of hepatic nuclear function during hemorrhagic shock. Surg. Forum 25, 10–12 (1974)
Lefer, A.M., Daw, C.F., Berne, Q.M.: Cardiac and skeletal muscle metabolic energy stores in hemorrhagic shock. Amer. J. Physiol. 216, 483–486(1969)
Levin, N.W., Abrahams, O.L.: Allopurinol in patients with impaired renal function. Ann. rheum. Dis. 25, 681–687 (1966)
Levine, A.S., Sharp, H.L., Mitchell, J., Krewit, W., Nesbit, M.E.: Combination therapy with 6-mercaptopurine (NSC-755) and allopurinol (NSC-1390) during induction and maintenance of remission of acute leukemia in children. Cancer Chemother. Rep. 53, 53–57 (1969)
Lyon, G.M.: Allopurinol and cytotoxic agents. J. Amer. med. Ass. 228, 1371 (1974)
Manzke, H., Dorner, K.: Effect of allopurinol on erythrocyte ATP and a 2,3-diphosphoglycerate levels and hemoglobin oxygen affinity in man. Arch. clin. Pharmacol. Ther. 3, 107 (1975)
Massey, V., Komai, H., Palmer, G., Elion, G.B.: On the mechanism of inactivation of xanthine oxidase by allopurinol and other pyrazolo(3,4-d)pyrimidines. J. biol. Chem. 245, 2837–2844 (1970)
Massey, V., Komai, H., Palmer, G., Elion, G.B.: The existence of nonfunctional active sites in milk xanthine oxidase; reaction with functional active site inhibitors. Vitam. Horm. 28, 505–531 (1970 a)
Mazur, A., Carleton, A.: Hepatic xanthine oxidase and ferritin iron in the developing rat. Blood 26, 317–322(1965)
Mazur, A., Green, S., Saha, A., Carleton, A.: Mechanism of release of ferritin in vivo by xanthine oxidase. J. clin. Invest. 37, 1809–1817 (1958)
McCollister, R.J., Gilbert, W.R., Ashton, D.M., Wyngaarden, J.B.: Pseudofeedback inhibition of purine synthesis by 6-mercaptopurine ribonucleotide and other purine analogues. J. biol. Chem. 239, 1560–1563 (1964)
McDaniel, H.G., Podgainy, H., Bressler, R.: The metabolism of tolbutamide in rat liver. J. Pharmacol, exp. Ther. 167, 91–97 (1969)
Miller, R.L., Adamczyk, D.L.: Inosine 5-monophosphate dehydrogenase from sarcoma 180 cells-substrate and inhibitory specificity. Biochem. Pharmacol. 25, 883–888 (1976)
Moon, R. J.: Tryptophan oxygenase and tryptophan metabolism in endotoxin-poisoned and allopurinol treated mice. Biochim. biophys. Acta (Amst.) 230, 342–348 (1971)
Morita, M., Feller, D.R., Gillette, J.R.: Reduction of niridazole by rat liver xanthine oxidase. Biochem. Pharmacol. 20, 217–226 (1971)
Nelson, D. J.: Unpublished
Nelson, D.J., Bugge, C.J.L., Krasny, H.C., Elion, G.B.: Formation of nucleotides of 6-14C oxipu-rinol in rat tissues and effects on uridine nucleotide pools. Biochem. Pharmacol. 22, 2003–2033 (1973)
Nelson, D.J., Elion, G.B.: Metabolism of [6-14C] allopurinol-lack of incorporation of allopurinol into nucleic acids. Biochem. Pharmacol. 24, 1235–1237 (1975)
Oster, K.A.: Treatment of angina pectoris according to a new theory of its origin. Cardiol. Dig. 3, 29–34(1968)
Oster, K. A.: Plasmalogen diseases: a new concept of the etiology of the atherosclerotic process. Am. J. Clin. Res. 2, 30–35 (1971)
Owens, M.L., Lazarus, H.M., Wolcott, M.W., Maxwell, J.G., Taylor, J.B.: Allopurinol and hypo-xanthine pretreatment of canine kidney donors. Transplantation 17, 224–227 (1974)
Pak, C.Y.C., Arnold, L.H.: Heterogeneous nucleation of calcium oxalate by seeds of monosodium urate. Proc. Soc. exp. Biol. (N.Y.) 149, 930–932 (1975)
Parker, J. C, Smith, E.E.: Effects of xanthine oxidase inhibition in cardiac arrest. Surgery 71, 339–344 (1972)
Payne, M.R., Dancis, J., Berman, P.H., Balis, M.E.: Inosine kinase in leucocytes of Lesch-Nyhan patients. Exp. Cell Res. 59, 489–490 (1970)
Pomales, R., Bieber, S., Friedman, R., Hitchings, G.H.: Augmentation of the incorporation of hypoxanthine into nucleic acids by the administration of an inhibitor of xanthine oxidase. Biochim. biophys. Acta (Amst.) 72, 119–120 (1963)
Pomales, R., Elion, G.B., Hitchings, G.H.: Xanthine as a precursor of nucleic acid purines in the mouse. Biochim. biophys. Acta (Amst.) 95, 505–506 (1965)
Powell, L.W.: Effects of allopurinol in iron storage in the rat. Ann. rheum. Dis. 25, 697–699 (1966)
Powell, L.W., Emmerson, B.T.: Haemosiderosis associated with xanthine oxidase inhibition. Lancet 1966 I, 239–240
Prien, E.L., Prien, E.L.: Composition and structure of urinary stone. Amer. J. Med. 45, 654–672 (1968)
Ragab, A.H., Gilkerson, E., Myers, M.: The effect of 6-mercaptopurine and allopurinol on granulopoiesis. Cancer Res. 34, 2246–2249 (1974)
Rawlins, M.D., Smith, S. E.: Influence of allopurinol on drug metabolism in man. Brit. J. Pharmacol. 48, 693–698 (1973)
Rodnan, G.P., Robin, J.A., Tolchin, S.F., Elion, G.B.: Allopurinol and gouty hyperuricemia. Efficacy of a single daily dose. J. Amer. med. Ass. 231, 1143–1147 (1975)
Romas, N., Fingerhut, B., Feigelson, P., Veenema, R.: Apparent inhibition of bladder carcinogenesis in the rat by allopurinol. Proc. Amer. Ass. Cancer Res. 14, 95 (1973)
Rosenbloom, F.M., Kelley, W.N., Miller, J.M., Seegmiller, J.E.: An enzymatic biochemical basis for variation in response to allopurinol. Arthr. and Rheum. 10, 307 (1967)
Rundles, R.W.: Allopurinol in gouty nephropathy and renal dialysis. Ann. rheum. Dis. 25, 694–696 (1966)
Rundles, R.W.: Metabolic effects of allopurinol and alloxanthine. Ann. rheum. Dis. 25, 615–620 (1966a)
Rundles, R.W., Elion, G.B.: Unpublished Rundles, R.W., Elion, G.B., Hitchings, G.H.: Allopurinol in the treatment of gout and secondary hyperuricemia. Bull. rheum. Dis. 161, 400–403 (1966a)
Rundles, R.W., Metz, E., Silberman, H.R.: Allopurinol in the treatment of gout. Ann. intern. Med. 64, 229–258 (1966)
Rundles, R.W., Wyngaarden, J.B., Hitchings, G.H., Elion, G.B.: Drugs and uric acid. Ann. Rev. Pharmacol. 9, 345–362 (1969)
Rundles, R.W., Wyngaarden, J.B., Hitchings, G.H., Elion, G.B., Silberman, H.R.: Effects of a xanthine oxidase inhibitor on thiopurine metabolism, hyperuricemia and gout. Trans. Ass. Amer. Phycns 76, 126–140 (1963)
Ryckewaert, A.: Les indications du traitement de fond de la goutte. Cah. Med. 11, 669–673 (1970)
Scott, J.T. (Ed.): Symposium on allopurinol. Ann. rheum. Dis. 25(6), 599–718 (1966)
Scott, J.T., Hall, A.P., Grahame, R.: Allopurinol in the treatment of gout. Brit. med. J. 1966 II, 321–327
Seegmiller, J.E., Engelman, K., Klinenberg, J.R., Watts, R.W.E., Sjoerdsma, A.: Xanthine oxidase and iron. New Engl. J. Med. 270, 534–535 (1964)
Seegmiller, J.E., Rosenbloom, F.M., Kelley, W.N.: Enzyme defect associated with a sex-linked human neurological disorder and excess purine synthesis. Science 155, 1682–1684 (1967)
Serre, H., Simon, L., Claustre, J.: Les urico-freinateurs dans le traitement de la goutte: à propos de 126 cas. Sem. Hôp. Paris 46, 3295–3301 (1970)
Shatney, C.H., MacCarter, D.J., Lillehei, R.C.: Effect of allopurinol, propanolol, and methylpred-nisolone on infarct size in experimental myocardial infarction. Amer. J. Cardiol. 37, 572–580 (1976)
Simmonds, H.A.: Urinary excretion of purines, pyrimidines, pyrazolopyrimidines in patients treated with allopurinol or oxipurinol. Clin. chim. Acta 23(2), 353–364 (1969)
Simmonds, H.A., Cadenhead, A., Cameron, J.S., Rising, T.J., Grahame, R., Dean, B.M.: Thiopurinol and purine metabolism. Metabolic and radioisotope studies. Ann. rheum. Dis. 33, 548–553 (1974)
Simmonds, H.A., Levin, B., Cameron, J.S.: Variations in allopurinol metabolism by xanthinuric subjects. Clin. Sci. molec. Med. 47, 173–178 (1974a)
Simmonds, H.A., Van Acker, K.J., Cameron, J.S., McBurney, A., Snedden, W.: Purine excretion in complete adenine phosphoribosyltransferase deficiency: effect of diet and allopurinol therapy. J. clin. Chem. clin. Biochem. 14, 321 (1976)
Sjoberg, K.-H.: Allopurinol therapy of gout with renal complications. Ann. rheum. Dis. 14, 688–690 (1966)
Skipper, H.E, Robins, R.K., Thomson, J.R., Cheng, C.C., Brockman, R.W., Schabel, F.M. Jr.: Structure activity relationships observed on screening a series of pyrazalopyrimidines against experimental neoplasms. Cancer Res. 17, 579–596 (1957)
Smith, M.J.V.: Placebo vs. allopurinol for renal calculi. J. Urol. (in press) (1977)
Smith, M.J.V., Boyce, W.H.: Allopurinol and urolithiasis. J. Urol. 102, 750–753 (1969)
Sorensen, L.: Seminars on the Lesch-Nyhan syndrome; management and treatment, discussion. Fed. Proc. 27, 1097 (1968)
Spector, T.: Inhibition of urate production by allopurinol. Biochem. Pharmacol. 26, 355–358 (1977)
Spector, T., Johns, D.G.: Stoichiometric inhibition of reduced xanthine oxidase by hydroxypyrazolo[3,4-d]pyrimidines. J. biol. Chem. 245, 5079–5085 (1970)
Spector, T., Johns, D.G.: 4-Hydroxypyrazolo(3,4-d)pyrimidine as a substrate for xanthine oxidase: loss of conventional substrate activity with catalytic cycling of the enzyme. Biochem. Biophys. Res. Commun. 38, 583–589 (1970a)
Stanley, E.L.: Allopurinol, a generalized coronary vasodilator. Circulation 43–44, 229 (1971)
Sweetman, L.: Urinary and cerebrospinal fluid oxypurine levels and allopurinol metabolism in the Lesch-Nyhan syndrome. Fed. Proc. 27, 1055–1058 (1968)
Tatsumi, K., Yamaguchi, T., Yoshimura, H.: Metabolsm of drugs. LXXX. The metabolic fate of nitrofuran derivatives. (3) Studies on enzymes in small intestinal mucosa of rat catalyzing degradation of nitrofuran derivatives. Chem. Pharm. Bull. (Tokyo) 21, 622–628 (1973)
Tax, W. J.M., Veerkamp, J.H., Trijbels, F.J.M., Schretlen, E.D. A.M.: Mechanism of allopurinolmediated inhibition and stabilization of human orotate phosphoribosyltransferase and orotidine phosphate decarboxylase. Biochem. Pharmacol. 25, 2025–2032 (1976)
Tersigni, R., Toledo-Pereyra, L.H., Najarian, J.S.: Effects of methylprednisolone, glucagon, and allopurinol in the protection of pancreaticoduodenal allografts perfused for twenty-four hours. Surgery 78, 599–607 (1975)
Tjandramaga, T.B., Cucinell, S.A., Iscaili, Z.H., Perel, J.M., Dayton, P.G., Yii, T.-F., Gutman, A.B.: Observations on the disposition of probenecid in patients receiving allopurinol. Pharmacology 8(4–6), 259–272 (1972)
Toledo-Pereyra, L.H., Najarian, J.S.: Total recovery of ischemic kidneys treated with allopurinol before transplantation. Surg. Forum 24, 302–304 (1973)
Toledo-Pereyra, L.H., Najarian, J.S.: Allopurinol on renal preservation. Transplantation 20, 256 (1975)
Toledo-Pereyra, L.H., Simmons, R.L., Najarian, J.S.: Protection of the ischemic liver by donor pretreatment before transplantation. Amer. J. Surg. 129, 513–517 (1975)
Toledo-Pereyra, L.H., Simmons, R.L., Olson, L.C., Najarian, J.S.: Clinical effect of allopurinol on preserved kidney. A randomized double blind study. Ann. Surg. 185, 128–131 (1977)
Udall, V.: Hepatic iron storage. Ann. Rheum. Dis. 25, 704 (1966)
Utter, M.F.: Guanosine and inosine nucleotides. In: Boyer, P.D., Lardy, H., Myrbäck, K. (Eds.): The Enzymes, Vol. 2, pp. 75–88. New York: Academic Press 1960
Vasko, K.A., De Wall, R.A., Riley, A.M.: Effect of allopurinol in renal ischemia. Surgery 71, 787–790 (1972)
Vesell, E.S., Passanti, G.T., Greene, F.E.: Impairment of drug metabolism in man by allopurinol and nortryptyline. New Engl. J. Med. 283, 1484–1488 (1970)
Vogler, W.R., Bain, J.A., Huguley, C.M., Palmer, H.G. Jr., Lowrey, M.E.: Metabolic and therapeutic effects of allopurinol in patients with leukemia and gout. Amer. J. Med. 40, 548–549 (1966)
Walker, R.I., Horvath, W.L., Rule, W.S., Herion, J.C., Palmer, J.G.: The failure of allopurinol to enhance 6-mercaptopurine toxicity in rabbits. Cancer Res. 33, 755–758 (1973)
Wang, C.Y., Hayashida, S., Pamukcu, A.M., Brian, G.T.: Enhancing effect of allopurinol on the induction of bladder cancer in rats by N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide. Cancer Res. 36, 1551–1555(1976)
Watts, R.W.E., Engelman, K., Klinenberg, J.R., Sjoerdsma, A., Seegmiller, J.E.: Enzyme defect in a case of xanthinuria. Nature (Lond.) 201, 395–396 (1964)
Watts, R.W.E., Snedden, W., Parker, R.A.: A quantitative study of skeletal-muscle purines and pyrazolo(3,4-d)pyrimidines in gout patients treated with allopurinol. Clin. Sci. 41, 153–158 (1971)
Watts, R.W. E., Watts, J.E.M., Seegmiller, J.E.: Xanthine oxidase activity in human tissues and its inhibition by allopurinol (4-hydroxypyrazolo-[3,4-d]pyrimidine). J. Lab. clin. Invest. 66, 688–698 (1965)
Way, J.L., Parks, R.E., Jr.: Enzymatic synthesis of 5′-phosphate nucleotides of purine analogs. J. biol. Chem. 231, 467–480 (1958)
Welch, R.M.: Drug-protein binding: A method for studying the interaction of drugs with bishydroxycoumarin (dicoumarol) in dogs. Ann. N.Y. Acad. Sci. 226, 259–266 (1973)
Wenzelides, K., Guski, H., Seidler, E., Meyer, R.: The influence of allopurinol on the alterations in the myocardium and the frequency of myocardial infarction in the hearts of rats under various experimental conditions. Dtsch. Gesundh.-Wes. 30, 183 (1975)
Wenzelides, K., Meyer, R.: The influence of allopurinol upon the size of the experimental myocardial infarction in the rat. Dtsch. Gesundh.-Wes. 30, 229 (1975)
Westerfeld, W.W., Richert, D.A., Bloom, R.J.: Inhibition of xanthine and succinic oxidases by carbonyl reagents. J. biol. Chem. 234, 1889–1896 (1959)
Wood, M.H., O’Sullivan, W. J., Wilson, M., Tiller, D.J.: Potentiation of an effect of allopurinol on pyrimidine metabolism by chlorothiazide in man. Clin. exp. Pharmacol. Physiol. 1, 53–58 (1974)
Wood, M.H., Sebel, E., O’Sullivan, W.J.: Allopurinol and thiazides. Lancet 1972 I, 751
Worthy, T.E., Grobner,W., Kelley,W.N.: Hereditary orotic aciduria: evidence for structural gene mutation. Proc. nat. Acad. Sci. (Wash.) 71, 3031–3035 (1974)
Yii, T.-F., Balis, M.E., Krenitsky, T.A., Dancis, J., Silvers, D.N., Elion, G.B., Gutman, A.B.: Rarity of X-linked partial hypoxanthine-guanine phosphoribosyltransferase deficiency in a large gouty population. Ann. intern. Med. 76, 255–264 (1972)
Yu, T.-F., Gutman,A.B.: Study of the paradoxical effects of salicylate in low, intermediate, and high dosage on the renal mechanisms for excretion of urate in man. J. clin. Invest. 38, 1298–1315 (1959)
Yii, T.-F., Gutman, A.B.: Effect of allopurinol (4-hydroxypyrazolo(3,4-d)pyrimidine) on serum and urinary uric acid in primary and secondary gout. Amer. J. Med. 37, 885–898 (1964)
Zuckerman, R., Drell, W., Levin, M.H.: Urinary purines in gout: effect of azaserine. Arthr. And Rheum. 2, 46–47 (1959)
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1978 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Elion, G.B. (1978). Allopurinol and Other Inhibitors of Urate Synthesis. In: Kelley, W.N., Weiner, I.M. (eds) Uric Acid. Handbook of Experimental Pharmacology, vol 51. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-66867-8_21
Download citation
DOI: https://doi.org/10.1007/978-3-642-66867-8_21
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-66869-2
Online ISBN: 978-3-642-66867-8
eBook Packages: Springer Book Archive