Abstract
The discovery of the antibacterial activity of sulfonamides1 in 1930’s marked the beginning of the era of modern antibacterial drug research. Subsequent observation of variations in the activities of these compounds by structural changes brought into sharp focus the power of molecular modification in drug development. The elucidation of the relationship between sulfanilamide and p-aminobenzoic acid provided one long sought-after mechanistic basis for a biochemical approach to chemotherapy. Much of the subsequent work in chemotherapy, and drug research in general, has been based on consideration of these facts.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Alleaume, P. M., et J. DeCap: Affmement Tridimensionnel du Sulfanilamide. Acta Cryst. B24, 214 (1968).
Amstutz, E. D.: Studies in the sulfone series VII. The preparation of 2, 8-diaminophenoxathiin-5-dioxide and bis-(2-hydroxy-4-aminophenyl)sulfone. J. Am. Chem. Soc. 72, 3420 (1950).
Anand, N., G. N. Vyas, and M. L. Dhar: Studies in potential antimycobacterial agents: Part I. Synthesis of p-alkylamino-p′-(galactosylamino)-diphenylsulfones. J. Sci. Ind. Res. (India) 12B, 353 (1953).
Anand, N., P. S. Wadia, and M. L. Dhar: Studies in potential antimycobacterial agents: Part III. Synthesis of p-(ω-hydroxy-alkylamino, ω-alkoxyalkylamino & haloethylamino)-p′-aminodiphenyl-sulfones. J. Sci. Ind. Res. (India) 13B, 260 (1954).
Anderson, E. S.: Ecology and epidemiology of transferable drug resistance. Bacterial episomes & Plasmids. A Ciba Foundation Symposium, ed. by G.W.W. Wolstenholme and Maeve O’Connor, p. 102. London: J. & A. Churchill Ltd. 1969.
Angier, R. B., J. H. Boothe, B. L. Hutchings, J. H. Mowat, J. Semb, E. L. R. Stokstad, Y. SubbaRow, C. W. Waller, D. B. Cosulich, M. J. Fahrenbach, M. E. Hultquist, E. Kuh, E. H. Northey, D. R. Seeger, J. P. Sickless, and J. M. Smith, Jr.: The structure and synthesis of the liver L. casei factor. Science 103, 667 (1946).
Archibald, H. M., and C. M. A. Ross: Preliminary report on the effect of diaminodiphenylsulphone on malaria in northern Nigeria. J. Trop. Med. Hyg. 63, 25 (1960).
Baker, B. R., M. V. Querry, and A. F. Kadish: Sulfones II. Derivatives of 4, 4′-diaminodiphenylsulfone. J. Org. Chem. 15, 402 (1950).
Basu, P. C., N. N. Singh, and N. Singh: Potentiation of activity of diphenylsulfone and pyrimethamine against P. gallinaceum and P. cynomolgi bastianellii. Bull. World Health Organ. 31, 699 (1964).
Bell, P. H., and R. O. Roblin, Jr.: Studies in chemotherapy. VII. A theory of the relation of structure to activity of sulfanilamide type compounds. J. Am. Chem. Soc. 64, 2905 (1942).
Biocca, E.: Quimioterapia sulfonica da toxoplasmose. Arquiv. Biol. (Sao Paulo) 7, 27 (1943).
Bishop, A.: Some recent developments in the problem of drug resistance in malaria. Parasitology 53, 10p (1963).
Blanchardv, K. C.: The isolation of p-aminobenzoic acid from yeast. J. Biol. Chem. 140, 919 (1941).
Bratton, A. C., and E. K. Marshall, Jr.: A new coupling component for sulphanilamide determination. J. Biol. Chem. 128, 537 (1939).
Bridges, J. W., S. R. Walker, and R. T. Williams: Species difference in the metabolism of sulfasomidine and sulfamethomidine. Biochem. J. 111, 173 (1969).
Brown, G. M.: The biosynthesis of folic acid. Inhibition by sulfonamides. J. Biol. Chem. 237, 536 (1962).
Brown, G. M.: The biosynthesis of pteridines. Advan. Enzymol. 35, 35 (1971).
Brown, G. M., R. A. Weisman, and D. A. Molnar: The biosynthesis of folic acid: I. Substrate and cofactor requirements for enzymatic synthesis by cell-free extracts of Escherichia coli. J. Biol. Chem. 236, 2539 (1961).
Browne, S. G.: The evaluation of present antileprosy compounds. Advan. Pharmacol. Chemother. 7, 211 (1969).
Browne, S. G.: Dapsone-resistant M. leprae in a patient receiving dapsone in low doses. Intern. J. Leprosy 37, 296 (1969).
Browne, S. G., and T. F. Davey: Diaminodiphenylsulphoxide in the treatment of leprosy: A definitive report on expanded trials. Leprosy Rev. 32, 194 (1961).
Brownlee, G., A. F. Green, and M. Woodbine: Sulphetrone: A chemotherapeutic agent for tubercu- losis: Pharmacology and chemotherapy. Brit. J. Pharmacol. 3, 15 (1948).
Brueckner, A. H.: The effect of pH on sulphonamide activity. Yale J. Biol. Med. 15, 813 (1943).
Bushby, S. R. M., and A. J. Woiwood: Excretion products of 4: 4′-diamino-diphenylsulfone. Am. Rev. Tuberc. Pulmonary Diseases 72, 123 (1955).
Bushby, S. R. M., and A.J. Woiwood: The identification of the major diazotizable metabolite of 4: 4′-diaminodiphenylsulphone in rabbit urine. Biochem. J. 63, 406 (1956).
Buu-Hoi, N. P.: The selection of drug for chemotherapy in leprosy. Intern. J. Leprosy 22, 16 (1954).
Cammarata, A., and R. C. Allen: Observations concerning the correlation of in vitro sulfonamide activity with pKa and Hammett values. J. Pharm. Sci. 56, 640 (1967).
Cenedella, R. J., and J. J. Jarrell: Suggested new mechanisms of antimalarial action for DDS involving inhibition of glucose utilization by the intraerythrocytic parasite. Am. J. Trop. Med. Hyg. 19, 592 (1970).
Coggeshall, L. T., J. Maier, and C. A. Best: The effectiveness of two new types of chemotherapeutic agents in malaria: sodium p, p′- diaminodiphenylsulphone-N N′-di dextrosesulfonate (Promin) and 2-sulfanilamidopyrimidine (sulfadiazine). J. Am. Med. Assoc. 177, 1077 (1941).
Cohen, S. N., and C. A. Miller: Non-chromosomal antibiotic resistance in bacteria. III Isolation of the discrete transfer unit of the R-factor RI. Proc. Natl. Acad. Sci. U.S. 67, 510 (1970a).
Cohen, S. N., and C. A. Miller: Non-chromosomal antibiotic resistance in bacteria. II Molecular nature of R-factors isolated from Proteus mirabilis and E. coli. J. Mol. Biol. 50, 671 (1970b).
Connar, R. G., T. B. Ferguson, W. C. Sealy, and N. F. Conant: Report of a single case with recovery. J. Thorac. Surg. 22, 424 (1951).
Cowdry, E.V., and C. Ruangsiri: Influence of promin, starch and heptaldehyde in experimental leprosy in rats. Arch. Pathol. 32, 632 (1941).
Cowles, P. B.: Ionisation and the bacteriostatic action of sulfonamides. Yale J. Biol. Med. 14, 599 (1942).
Davenport, H. W., and A. E. Wilhelmi: Renal carbonic anhydrase. Proc. Soc. Exptl. Biol. Med. 48, 53 (1941).
Davis, B. D.: Binding of sulfonamide drugs by plasma proteins. Science 95, 78 (1942).
Deininger, R., and H. Gutbrod: The pharmacodynamic action of the new sulfonamide, 2-(p-aminobenzene-sulfonamido)-4,5-dimethyl-oxazole. Arzneimittel-Forsch. 10, 612 (1960).
Domagk, G.: Ein Beitrag zur Chemotherapie der bakteriellen Infektionen. Deut. Med. Wochschr. 61, 250 (1935).
Donovick, R., A. Bayan, and D. Hamre: The reversal of the activity of antituberculous compounds in vitro. Am. Rev. Tuberc. 66, 219 (1952).
Ellard, G. A.: Absorption, metabolism and excretion of Di(p-aminophenyl)sulphone (Dapsone) and Di(p-aminophenyl)sulphoxide in man. Brit. J. Pharmacol. 26, 212 (1966).
Elslager, E. F.: Progress in malaria chemotherapy. Part I. Repository antimalarial drugs. Progr. Drug. Res. Vol. 13, 170 (1969).
Elslager, E. F., and D. F. Worth: Repository antimalarial drugs: N,N′-diacetyl-4,4′-diaminodiphenylsulfone and related 4-acylaminodiphenylsulfones. Nature 206, 630 (1965).
Eyles, D. E.: Newer knowledge of the chemotherapy of toxoplasmosis. Ann. N. Y. Acad. Sci. 64, 252 (1956).
Eyles, D. E., and N. Coleman: An evaluation of the curative effects of pyrimethamine and sulfadiazine, alone and in combination, on experimental mouse toxoplasmosis. Antibiot. & Chemotherapy 5, 529 (1955).
Feldman, W. H., H. C. Hinshaw, and H. E. Moses: Promin in experimental tuberculosis. Am. Rev. Tuberc. 45, 303 (1942).
Fildes, P.: Rational approach to research in chemotherapy. Lancet 1940-1, 955.
Findlay, G. M.: The action of sulfanilamide on the virus of lymphogranuloma venereum. Brit. J. Exptl. Pathol. 21, 356(1940).
Flake, R. E., J. Griffin, E. Townsend, and E.M. Yow: Studies of the absorption, distribution and excretion of acetyl sulfisoxazole, an insoluble sulfonamide appearing as sulfisoxazole in the blood. J. Lab. Clin. Med. 44, 582 (1954).
Foernzler, E. C., and A. N. Martin: Molecular orbital calculations on sulfonamide molecules. J. Pharm. Sci. 56, 608 (1967).
Forster, W. G., and J. R. McGibony: Trachoma. Am. J. Ophthalmol. 27 C, 1107 (1944).
Fox, C. L. Jr., and H. M. Rose: Ionisation of sulfonamides. Proc. Soc. Exptl. Biol. Med. 50, 142 (1942).
Franke, H., und J. Fuchs: Ein neues antidiabetisches Prinzip (Ergebnisse klinischer Untersuchungen). Deut. Med. Wochschr. 80, 1449 (1955).
Friedkin, M.: Enzymatic aspects of folic acid. Ann. Rev. Biochem. 32, 185 (1963).
Fujita, T.: Hydrophobic bonding of sulfonamide drugs with serum albumin. J. Med. Chem. 15, 1049 (1972).
Fujita, T., and C. Hansch: Analysis of the structure-activity relationship of the sulfonamide drugs using substituent constants. J. Med. Chem. 10, 991 (1967).
Fuller, A. T.: Is p-aminobenzenesulfonamide an active agent in prontosil therapy? Lancet 1937-11, 194.
Fust, B., and E. Bohni: Tolerance and antibacterial properties of 2, 4-dimethoxy-6-sulfanilamido-l,3-diazine (Madribon) and some other sulfonamides. Antibiot. Med. Clin. Therapy 6, 3 (1959).
Fust, B., and E. Bohni: Vergleichende experimentelle Untersuchungen mit 5-Methy 1-3-sulfanilamido-isoxazol und anderen Sulfanilamiden und Antibiotica. Schweiz, med. Wochschr. 92, 1599 (1962).
Garrett, E. R., J. B. Mielck, J. K. Seydel, and H.J. Kessler: Kinetics and mechanisms of action of drugs on microorganisms. VIII. Quantification and prediction of the biological activities of m- and p-substituted N′-phenylsulfanilamides by microbial kinetics. J. Med. Chem. 12, 740 (1969).
Garrod, L. P., D. G. James, and A. A. G. Lewis: The synergy of trimethoprim and sulfonamides. Proc. of Conf. at Royal Coll. Physicians, May 1969, Postgrad. Med. J. (Supplement) 45, 1 (1969).
Glazko, A. J., W. A. Dill, R. G. Montalbo, and E.L. Holmes: A new analytical procedure for dapsone: Application to blood level and urinary-excretion studies in normal men. Am. J. Trop. Med. Hyg. 17 (3), 465 (1968).
Gots, J. S.: Occurrence of 4-amino-5-imidazolecarboxamide as a pentose derivative. Nature 172, 256 (1953).
Green, H. N.: The mode of action of sulfanilamide. Brit. J. Exptl. Pathol. 21, 38 (1940).
Greenberg, J.: The antimalarial activity of 2, 4-diamino-6,7-diphenylpterin; its potentiation by sulphadiazine and inhibition by pteroylglutamic acid. J. Pharmacol. Exptl. Therap. 97, 484 (1949).
Gupta, S. K., and R. N. Chakravarti: The therapeutic activity of some sulphones and sulphoxides in experimental tuberculosis of guineapigs. Brit. J. Pharmacol. 10, 113 (1955).
Gupta, S. K., and I. S. Mathur: Therapeutic activity of S.N.44 (p-ethylamino-p′-aminodiphenylsulphone) and S. N.47 (p-isobutylamino-p′-aminodiphenylsulphone) in experimental tuberculosis of mice. J. Sci. Ind. Res. (India) 16C, 192 (1957).
Gupta, S. K., and I. S. Mathur: The evaluation of some nuclear and side-chain substituted sulfones in experimental tuberculosis of guineapigs. Arch. Intern. Pharmacodyn. 64, 354 (1958).
Hays, W.: What are episomes and plasmids? Bacterial episomes and plasmids. A Ciba Foundation Symposium, ed. by G.W.W. Wostenholme & Maeve O’Connor, p. 4. London: J. & A. Churchill Ltd. 1969.
Henry, R. J.: The mode of action of sulphonamides. Bacteriol. Rev. 7, 175 (1943).
Hill, R. A., and H. M. Goodwin, Jr.: 5th Med. J. Nashville 30, 1170 (1937) (quoted by Richards, 1970).
Hitchings, G. H., and J. J. Burchall: Inhibition of folate biosynthesis and function as a basis for chemotherapy. Advanc. Enzymol. 27, 417 (1965).
Hotchkiss, R. D., and A. H. Evans: Fine structure of a genetically modified enzyme as revealed by relative affinities for modified substrate. Federation Proc. 19, 912 (1960).
Irmscher, K., D. Gabe, K. Jahnke und W. Scholtan: Untersuchungen zur Serumeiweißbindung und zur renalen Elimination von isomeren Sulfonamiden (5-Sulfanilamido-3-athyl-l,2,4-thiodiazol und 5-Sulfanilamido-2-athyl-l,3,4-thiodiazol). Arzneimittel-Forsch. 16(8), 1019 (1966).
Iwai, K., and O. Okinaka: The biosynthesis of folic acid compounds in plants. II Some properties of dihydropteroate-synthesizing enzyme in pea seedlings. J. Vitaminol. (Kyoto) 14, 170 (1968).
Jaenicke, L., und P. C. Chan: Die Biosynthese der Folsäure. Angew. Chem. 72, 752 (1960).
Jafary, M. H., and G. J. Burke: Antibiotics and salmonella excretors. Brit. Med. J. 1970, 605, also see editorial review 3, 297 (1970).
Janbon, M., J. Chaptal, A. Vedel, and J. Schaap: Accidents hypoglycemiques granes par un sulfamidothiazol (le VK57 OU 2254 RP). Montpellier. Med. 21–22, 441 (1942).
Jawetz, E.: Chemotherapy of chlamydial infections. Advanc. Pharmacol. Chemother. 7, 253 (1969).
Jones, L. P., and F. D. Williams: Rhizopterin biosynthesis in Staphylococcus epidermidis. Can. J. Microbiol. 14, 933 (1968).
Joyner, L. P., S. F. M. Davies, and S. B. Kendall: Chemotherapy of coccidiosis. In: Experimental chemotherapy (ed. R.J. Schnitzer, and F. Hawking), p. 445. New York: Academic Press, 1963.
Kendall, S. B.: A comparison of the efficacy of sulphamezathine and sulphaquinozaline in the control of experimentally induced caecal coccidiosis in chicks. Vet. Record 62, 381 (1950).
Kendall, S. B., and L. P. Joyner: Potentiation of the coccidiostatic effects of sulphadimidine by five different folic acid, antagonists. Vet. Record 70, 632 (1958).
Khosla, M. C., P. S. Wadia, N. Anand, and M. L. Dhar: Studies in potential antimycobacterial agents: Part VIII — Metabolism and mode of excretion of p-ethylamino-p′-aminodiphenylsulfone and p-methylamino-p′-aminodiphenyl-sulphoxide. J. Sci. Ind. Res. (India) 14C, 152 (1955).
Klotz, I. M., and F. M. Walker: The binding of some sulfonamides by bovine serum albumin. J. Am. Chem. Soc. 70, 943 (1948).
Krüger-Thiemer, E.: Die Lösung pharmakologischer Probleme durch Rechenautomaten. Arzneimittel-Forsch. 16, 1431 (1966).
Krüger-Thiemer, E., und P. Bünger: Kumulation und Toxizität bei falscher Dosierung von Sulfanilamiden. Arzneimittel-Forsch. 11, 867 (1961).
Kurnosova, L. M., and M. M. Lenkevich: Mode of action of sulfonamides on trachoma virus. Acta Virol. 8, 350 (1964).
Lai, T. F., and R. E. Marsh: The crystal structure of p-aminobenzoic acid. Acta Cryst. 22, 855 (1967).
Lampen, J. O., and M. J. Jones: The antagonism of sulfonamide inhibition of certain lactobacilli and enterococci by pteroylglutamic acid and related compounds. J. Biol. Chem. 166, 435 (1946).
Lampen, J. O., and M. J. Jones: The growth-promoting and antisulfonamide activity of p-aminobenzoic acid, pteroylglutamic acid and related compounds for L. arahinosus and Strept. plantarum. J. Biol. Chem. 170, 133 (1947).
Landy, M., N. W. Larkun, E. J. Oswald, and F. Streightoff: Increased synthesis of p-aminobenzoic acid associated with the development of resistance in Staph. aureus. Science 97, 265 (1943).
Languillon, J.: La sulfamidotherapie dans le lepre. Sulfamethoxy-pyridazine, acetylsulfamethoxypyridazine, sulfadimethoxine, acetylsulfadimethoxine, R04-4393. Med. Trop. 24, 522 (1964).
Lascelles, J., and D. D. Woods: The synthesis of “folic acid" by Bacterium coli and Staphylococcus aureus and its inhibition by sulphonamides. Brit. J. Exptl. Pathol. 33, 288 (1952).
Lehr, D.: Inhibition of drug precipitation in the urinary tract by the use of sulfonamides mixtures. I. Sulfathiazole-sulfadiazine mixture. Proc. Soc. Exptl. Biol. Med. 58, 11 (1945).
Levine, P. P.: The effect of sulfanilamide on the course of experimental avian coccidiosis. Cornell Vet. 29, 309 (1939).
Levine, P. P.: The effect of sulfapyridine on experimental avian coccidiosis. J. Parasitol. 26, 233 (1940).
Linnell, W. H., and J. B. Stenlake: Nuclear derivatives of 4, 4′-diaminodiphenylsulfone. J. Pharm. Pharmacol. 2, 937 (1950).
Lockwood, J. S.: Action of sulfanilamide and its applications to surgical infections. J. Am. Med. Assoc. 111, 2259 (1938).
Maier, J., and E. Riley: Inhibition of antimalarial action of sulfonamides by p-aminobenzoic acid. Proc. Soc. Exptl. Biol. Med. 50, 152 (1942).
Mallett, E., and D. Musselwhite: The use of septrin in the treatment of upper respiratory tract infections. Practitioner 205, 807 (1970).
Mann, T., and D. Keilin: Sulfanilamide as a specific inhibitor of carbonic anhydrase. Nature 146, 164 (1940).
Marshall, E. K. (Jr.): Determination of sulfanilamide in blood and urine. J. Biol. Chem. 122, 263 (1937).
Martinek, K.: Wein. Med. Wochenschr. 120, 278 (1970).
McCallum, F. O., and G. M. Findlay: Chemotherapeutic experiments on the virus of lymphogranuloma inguinale in the mouse. Lancet 1938-II, 136.
Mietzsch, F., und J. Klarer: Herstellung von Azoverbindungen. Deutsches Reichspatent 607537 (1934).
Miller, A. K.: Folic acid and biotin synthesis by sulphonamide-sensitive and sulphonamide-resistant strains of Escherichia coli. Proc. Soc. Exptl. Biol. Med. 57, 151 (1944).
Miller, A. K., P. Bruno, and R. M. Berglund: The effect of sulfathiazole on the in vitro synthesis of certain vitamins by Escherichia coli. J. Bacteriol. 54, 9 (1947).
Miller, C. S.: Dialkylsulfamyl, benzoic acid. U.S. Patent, 2,608,507, Aug. 1952.
Miller, G. H., P. H. Doukas, and J. K. Seydel: Sulfonamide structure-activity relationship in a cell-free system. Correlation of inhibition of folate synthesis with antibacterial activity and physicochemical parameters. J. Med. Chem. 15, 700 (1972).
Mitsuda, H., and Y. Suzuki: Pteridines in plants. III. Biogenesis of folic acid in green leaves; inhibitors acting on the biosynthetic pathway for the formation of dihydropteroic acid from guanylic acid. J. Vitaminol. (Kyoto) 14, 106 (1968).
Morgan, H. R.: Studies on the relationship of pteroylglutamic acid to the growth of Psittacosis virus (strain 6BC). J. Exptl. Med. 88, 285 (1948).
Moriguchi, I., and N. Kaneniwa: Spectroscopic studies on molecular interactions. IV. Chargetransfer properties and antibacterial activity of sulfonamides. Chem. Pharm. Bull. (Tokyo) 17, 2554 (1969).
Moriguchi, I., and S. Wada: Protein bindings. IV. Relations of an index for electronic structure to binding constant with serum albumin and bacteriostatic activities of sulfonamides. Chem. Pharm. Bull. (Tokyo) 16, 734 (1968).
Moriguchi, I., S. Wada, and T. Nishizawa: Protein bindings. III. Binding of sulfonamides to bovine serum albumin. Chem. Pharm. Bull. (Tokyo) 16, 601 (1968).
Morrison, N. E.: Sulfone resistant states. Intern. J. Leprosy 36, Abst. No. 199 (1968).
Moulder, J. W.: The biochemistry of intracellular parasitism, p. 105. Chicago: University of Chicago Press 1962.
Mowat, J. H., J. H. Boothe, B. L. Hutchings, E. L. R. Stokstad, C. W. Waller, R. B. Angier, J. Semb, D. B. Cosulich, and Y. SubbaRow: Structure and synthesis of the pteridine degradation products of the fermentation L. casei factor. Ann. N. Y. Acad. Sci. 98, 279 (1946).
Nichols, R. L., W. F. Jones, and M. Finland: Sulfamethoxypyridazine: preliminary observations on absorption and excretion, a new long-acting antibacterial sulfonamide. Proc. Soc. Exptl. Biol. Med. 92, 637 (1956).
Nimmo-Smith, R. H., J. Lascelles, and D. D. Woods: Synthesis of folic acid by streptobacterium plantarum and its inhibition by sulfonamides. Brit. J. Exptl. Pathol. 29, 264 (1948).
Northey, E. H.: The sulfonamides and allied compounds. New York: Reinhold 1948.
Ortiz, P. J.: Dihydrofolate and dihydropteroate synthesis by partially purified enzymes from wild-type and sulfonamide-resistant pneumococcus. Biochemistry 9, 355 (1970).
Ortiz, P. J., and R. D. Hotchkiss: The enzymatic synthesis of dihydrofolate and dihydropteroate in cell-free preparations from wild-type and sulfonamide-resistant pneumococcus. Biochemistry 5, 67 (1966).
Pato, M. L., and G. M. Brown: Mechanisms of resistance of Escherichia coli to sulfonamides. Arch. Biochem. Biophys. 103, 443 (1963).
Pearson, J. M. H., J. H. S. Petit, and R. J. W. Rees: Studies on sulfone resistance in leprosy.3. A case of partial resistance. Intern. J. Leprosy 36, 171 (1968).
Pullman, B., and A. Pullman: Quantum biochemistry, p. 108. New York: Interscience Publishers 1963.
Ramakrishnan, S. P., P. C. Basu, H. Singh, and N. Singh: Studies on the toxicity and action of diaminodiphenylsulfone (DDS) in avian and simian malaria. Bull. World Health Organ. 27, 213 (1962).
Ramakrishnan, S. P., P. C. Basu, H. Singh, and B. L. Wattal: A study on the joint action of diaminodiphenylsulfone (DDS) and pyrimethamine in the sporogony cycle of Plasmodium gallinaceum: Potentiation of the sporontocidal activity of pyrimethamine by DDS. Indian J. Malariol. 17, 141 (1963).
Reber, M., G. Rutishauser und H. Tholen: Clearance-Untersuchungen am Menschen mit Sulfamethoxazol und Sulforthodimothoxin, 3rd int. Congr. Chemother., Stuttgart 1963, vol. 1, p. 648 (eds. H. P. Kuemmerle and Preziosi). Stuttgart: Thieme 1964.
Richards, W. H. G.: The combined action of pyrimidines and sulfonamides or sulfones in the chemotherapy of malaria and other protozoal infections. Advanc. Pharmacol. Chemother. 8, 121 (1970).
Richey, D. P., and G. M. Brown: The biosynthesis of folic acid. IX. Purification and properties of the enzymes required for the formation of dihydropteroic acid. J. Biol. Chem. 244, 1582 (1969).
Rieder, J.: Physikalisch-chemische und biologische Untersuchungen an Sulfonamiden. Arzneimittel-Forsch. 13, 81, 89, 95 (1963).
Rist, N.: Action du p-aminophenylsulfamide et de la p,p′-diamino-diphenylsulfone sur la culture des bacilles tuberculeux des mammiferes et des oiseaux. Compt. Rend. Soc. Biol. 130, 972 (1939).
Rubbo, S. D., and J. M. Gillepsie: p-Aminobenzoic acid as a bacterial growth factor. Nature 146, 838 (1940).
Sabin, A. B., and J. Warren: Therapeutic effect of the sulfonamides on infection by an intracellular protozoan (Toxoplasma). J. Bacteriol. 41, 80 (1941).
Schmelkes, F. C.: The mechanism of sulfonamide potentiation through ionisation and oxidation. J. Bacteriol. 45, 67 (1943).
Schnaare, R. S., and A. N. Martin: Quantum chemistry in drug design. J. Pharm. Sci. 54, 1707 (1965).
Schneider, J., and J. Languillon: The retard-action sulfonamides in the treatment of leprosy and the efficient action of acetyl-sulfamethoxypyridazine. Abstr. 8th Intern. Cong. Leprology, Rio de Janairo, 1963, p. 36 (1964).
Scholtan, W.: Die Bindung der Sulfonamide an Eiweißkörper. Arzneimittel-Forsch. 14, 348 (1964).
Scholtan, W.: Die hydrophobe Bindung der Pharmaka an Human-Albumin und Ribonucleinsäure. Arzneimittel-Forsch. 18, 505 (1968).
Schwartz, W. B.: The effect of sulfanilamide on salt and water excretion in congestive heart failure. New Engl. J. Med. 240, 173 (1949).
Seeler, A. O., O. Graessle, and E. D. Dusenbery: The effect of PAB on the chemotherapeutic activity of sulfonamides in lympho-granuloma venereum and in duck malaria. J. Bacteriol. 45, 205 (1943).
Selbie, F. R.: The inhibition of the action of sulfanilamide in mice by p-aminobenzoic acid. Brit. J. Exptl. Pathol. 21, 90 (1940).
Seydel, J. K.: Prediction of in vitro activity of sulfonamides, using Hammett constants or spectrophotometric data of the basic amines for calculation. Mol. Pharmacol. 2, 259 (1966).
Seydel, J. K.: Molecular basis for the action of chemotherapeutic drugs, structure-activity studies on sulfonamides. In: Physico-chemical aspects of drug action (ed. E.J. Ariens), p. 169. Pergamon Press 1968.
Seydel, J. K.: Physicochemical approaches to the rational development of new drugs. In: Drug design (ed. E.J. Ariens), p. 343. Vol. 1 Academic Press 1971a.
Seydel, J. K.: Prediction of the in vitro activity of sulfonamides synthesised from simple amines by use of electronic data obtained from the simple amines. J. Med. Chem. 14, 724 (1971b).
Seydel, J. K., E. Kruger-Thiemer, and E. Wempe: Relation between antibacterial activity and 1R of sulfanilamide. Z. Naturforsch. 15b, 628 (1960).
Shannon, J. A.: The relationship between chemical structure and physiological disposition of a series of substances allied to sulfanilamide. Ann. N. Y. Acad. Sci. 44, 455 (1943).
Shiota, T.: Enzymic synthesis of folic acid-like compounds by cell-free extracts of loctobacillus arabinosus. Arch. Biochem. Biophys. 80, 155 (1959).
Shiota, T.,C. M. Baugh, R. Jackson, and R. Dillard: The enzymatic synthesis of hydroxymethyldihydrofolate. Biochemistry 8, 5022 (1969).
Shiota, T., and M. M. Disraely: The enzymic synthesis of dihydrofolate from 2-amino-4-hydroxy-6-hydroxymethyl dihydropteridine and p-aminobenzoyl glutamate by extracts of Lactobacillus plantarum. Biochim. Biophys. Acta 52, 467 (1961).
Shiota, T., M. N. Disraely, and M. P. McCann: The enzymatic synthesis of folate-like compounds from hydroxymethyldihydropteridine pyrophosphate. J. Biol. Chem. 239, 2259 (1964).
Shive, W., W. C. Ackerman, M. Gordon, M. E. Getzendaner, and R. E. Eakin: 5(4)-Amino-4-(5)-imidazole-carboxamide, a precursor of purines. J. Am. Chem. Soc. 69, 725 (1947).
Shepard, C. C.: The experimental disease that follows the injection of human leprosy bacilli into the foot-pads of mice. J. Exptl. Med. 112, 445 (1960).
Shepard, C. C., D. H. McRae, and J. A. Habas: Sensitivity of M. leprae to low levels of 4, 4′-diaminodiphenylsulfone. Proc. Soc. Exptl. Biol. Med. 122, 893 (1966).
Shepard, C. C., J. G. Tolentino, and D. A. McRae: The therapeutic effect of 4,4-diacetyldiaminodiphenylsulfone (DADDS) in leprosy. Am. J. Trop. Med. Hyg. 17, 192 (1967).
Shepherd, R. G.: Sulfanilamides and other p-amino benzoic acid antagonists. In: Medicinal chemistry (ed. A. Burger), P. 255. Vol. 1: Wiley-Interscience 1970.
Shepherd, R. G., and A. Lewis: Synthesis of antibacterial agents. Ann. Rep. Med. Chem. 1966, 114.
Smith, M. I., M. J. Jackson, and H. Bauer: Evaluation of sulfones and streptomycin in experimental tuberculosis. Ann. N. Y. Acad. Sci. 52, 704 (1949).
Southworth, H.: Acidosis associated with the administration of sulfanilamide. Proc. Soc. Exptl. Biol. Med. 36, 58 (1937).
Stamp, T. C.: Bacteriostatic action of sulphanilamide in vitro. Lancet 1939–II, 10.
Stetten, M. R., and C. L. Fox: An amine formed by bacteria during sulphonamide bacteriostasis. J. Biol. Chem. 161, 333 (1945).
Stockstad, E. L. R.: The isolation of a nucleotide essential for the growth of L. casei. J. Biol. Chem. 139, 475 (1941).
Strauss, A. M., A. M. Kliggman, and D. M. Pillsbury: The chemotherapy of actinomycosis and nocardiosis. Am. Rev. Tuberc. 63, 441 (1951).
Struller, Th.: Long-acting and short-acting sulfonamides. Recent developments. Antibiot. Chemotherapia 14, 179 (1968).
Tandon, J. K., G. N. Vyas, and N. Anand: Studies in potential antimycobacterial agents. Part. XIV. Synthesis of p-alkylamino-p′-amino-o,m and m′-methoxy and hydroxy and m,m′-dimethoxy and dihydroxy-diphenylsulfones. J. Sci. Ind. Res. (India) 17B, 192 (1958).
Tarizzo, M. L.: Chemotherapy of trachoma. Chronicle World Health Organ. 26, 99 (1972).
Trefouel, J., Mme J. Trefouel, F. Nitti, and D. Bovet: Activite du p-aminophenylsulfamide surles infections streptococciques experimentales de la souris et du lapin. Compt. Rend. Soc. Biol. 120, 756 (1935).
Tripod, J., L. Neipp, W. Padowtz, and W. Sackmann: Relations experimentales entre l’action cura-
Tschesche, R.: A new explanation of the mode of action of the sulfonamides. Z. Naturforsch. 26b, 10 (1947).
Tsukamura, M.: The in vitro tuberculostatic action of sulfonamides. Chemotherapy (Japan) 3, 187 (1955).
Ueda, M., K. Orita, and T. Koizumi: Studies on metabolism of drug XIII. Quantitative separation of metabolites in human urine after oral administration of sulfisomezole and sulfaphenazole. Chem. Pharm. Bull. (Tokyo) 20, 2047 (1972).
Vyas, G. N., N. Anand, and M. L. Dhar: Studies in potential antimycobacterial agents: Part IV—Synthesis of p-alkylamino-p′-amino-o′-hydroxydiphenyl sulfones. J. Sci. Ind. Res. (India) 13B, 270 (1954).
Vyas, G. N., N. Anand, and M. L. Dhar: Studies in potential antimycobacterial agents: Part X—Synthesis of p-alkylamino-p′-amino-o,o′-dihydroxydiphenyl sulphones. J. Sci. Ind. Res. (India) 14C, 218 (1955).
Watanabe, T.: Infective heredity of multiple drug resistance in bacteria. Bacteriol. Rev. 27, 87 (1963).
Watanabe, T., and T. Fukasawa: Episomic resistance factors in Enterobacteriaceae. III. Elimination of resistance factors by treatment with acridine dyes. Med. Biol. (Tokyo) 56, 71 (1960).
Watanabe, T., and T. Fukasawa: Episome-mediated transfer of drug resistance in Enterobacteriaceae. III. Transduction of resistance factors. J. Bacteriol. 82, 202 (1961 a).
Watanabe, T., and T. Fukasawa: Episome-mediated transfer of drug resistance in Enterobacteriaceae. II. Elimination of resistance factors with acridine dyes. J. Bacteriol. 81, 679 (1961 b).
Weinstein, L., M. A. Madoff, and C. M. Samet: The sulfonamides. New Engl. J. Med. 263, 793, 842, 900(1960).
Weisman, R., and G. M. Brown: The biosynthesis of folic acid. V. Characteristics of the enzyme system that catalyzes the synthesis of dihydropteroic acid. J. Biol. Chem. 239, 326 (1964).
Welch, A. D., and C. A. Nichol: Water-soluble vitamins concerned with one- and two-C atom intermediates. Ann. Rev. Biochem. 21, 633 (1952).
Werner, A.: Tratemiento de la toxoplasmosis. Bol. Chileno Parasitol. 25, 65 (1970).
Williams, R. T., and D. V. Park: Metabolic fate of drugs. Ann. Rev. Pharmacol. 4, 85 (1964).
Wolf, B., and R. D. Hotchkiss: Genetically modified folic acid synthesizing enzymes of pneumococcus. Biochemistry 2, 145 (1963).
Woods, D. D.: Relation of p-aminobenzoic acid to mechanism of action of sulphanilamide. Brit. J. Exptl. Path. 21, 74 (1940).
Woods, D. D.: Metabolic relations between p-aminobenzoic and folic acids in micro-organisms. In: Chemistry and biology of pteridines, CIBA Foundation Symposium, p. 220. Boston, Mass.: Little Brown, 1954.
Yamazaki, M., N. Kakeya, T. Morishita, A. Kamada, and A. Aoki: Biological activity of drugs X. Relation of structure to the bacteriostatic activity of sulfonamides (1). Chem. Pharm. Bull. (Tokyo) 18, 702 (1970).
Yow, E. M.: A re-evaluation of sulfonamide therapy. Ann. Intern. Med. 43, 323 (1955).
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1975 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Anand, N. (1975). Sulfonamides and Sulfones. In: Corcoran, J.W., Hahn, F.E., Snell, J.F., Arora, K.L. (eds) Mechanism of Action of Antimicrobial and Antitumor Agents. Antibiotics, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46304-4_45
Download citation
DOI: https://doi.org/10.1007/978-3-642-46304-4_45
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-46306-8
Online ISBN: 978-3-642-46304-4
eBook Packages: Springer Book Archive