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Pathway Description
Acetyl sulfisoxazole Action Pathway
Escherichia coli (strain K12)
Category:
Metabolite Pathway
Sub-Category:
Drug Action
Created: 2023-08-29
Last Updated: 2025-05-31
Acetyl sulfisoxazole is an antibacterial from the sulfanilamide drug class. It is a broad-spectrum antibiotic indicated against urinary tract infections, meningococcal meningitis, acute otitis media, inclusion conjunctivitis, toxoplasmosis, and many others. Acetyl sulfisoxazole is a synthetic bacteriostatic, meaning that it stops the bacteria from growing. This drug binds competitively to the dihydropteroate synthase enzyme. This enzyme is essential to produce dihydrofolic acid in bacteria, when it is inhibited, the bacteria cannot grow anymore because they cannot produce DNA with the folic acid. Thus drug is administered as an oral tablet. N1-acetyl sulfisoxazole is metabolized to sulfisoxazole by digestive enzymes in the gastrointestinal tract and is absorbed as sulfisoxazole (the active compound).
References
Acetyl sulfisoxazole Pathway References
Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M: DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D1074-D1082. doi: 10.1093/nar/gkx1037.
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Suber RL, Lee C, Torosian G, Edds GT: Pharmacokinetics of sulfisoxazole compared in humans and two monogastric animal species. J Pharm Sci. 1981 Sep;70(9):981-4. doi: 10.1002/jps.2600700903.
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Pubmed: 16000430
Komatsu K, Ito K, Nakajima Y, Kanamitsu Si, Imaoka S, Funae Y, Green CE, Tyson CA, Shimada N, Sugiyama Y: Prediction of in vivo drug-drug interactions between tolbutamide and various sulfonamides in humans based on in vitro experiments. Drug Metab Dispos. 2000 Apr;28(4):475-81.
Pubmed: 10725317
Swedberg G, Fermer C, Skold O: Point mutations in the dihydropteroate synthase gene causing sulfonamide resistance. Adv Exp Med Biol. 1993;338:555-8. doi: 10.1007/978-1-4615-2960-6_113.
Pubmed: 8304179
Dallas WS, Gowen JE, Ray PH, Cox MJ, Dev IK: Cloning, sequencing, and enhanced expression of the dihydropteroate synthase gene of Escherichia coli MC4100. J Bacteriol. 1992 Sep;174(18):5961-70. doi: 10.1128/jb.174.18.5961-5970.1992.
Pubmed: 1522070
Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-62. doi: 10.1126/science.277.5331.1453.
Pubmed: 9278503
Bognar AL, Osborne C, Shane B: Primary structure of the Escherichia coli folC gene and its folylpolyglutamate synthetase-dihydrofolate synthetase product and regulation of expression by an upstream gene. J Biol Chem. 1987 Sep 5;262(25):12337-43.
Pubmed: 3040739
Kimlova LJ, Pyne C, Keshavjee K, Huy J, Beebakhee G, Bognar AL: Mutagenesis of the folC gene encoding folylpolyglutamate synthetase-dihydrofolate synthetase in Escherichia coli. Arch Biochem Biophys. 1991 Jan;284(1):9-16. doi: 10.1016/0003-9861(91)90254-g.
Pubmed: 1989505
Nonet ML, Marvel CC, Tolan DR: The hisT-purF region of the Escherichia coli K-12 chromosome. Identification of additional genes of the hisT and purF operons. J Biol Chem. 1987 Sep 5;262(25):12209-17.
Pubmed: 3040734
Bennett CD, Rodkey JA, Sondey JM, Hirschmann R: Dihydrofolate reductase: the amino acid sequence of the enzyme from a methotrexate-resistant mutant of Escherichia coli. Biochemistry. 1978 Apr 4;17(7):1328-37. doi: 10.1021/bi00600a030.
Pubmed: 350268
Stone D, Phillips AW, Burchall JJ: The amino-acid sequence of the dihydrofolate reductase of a trimethoprim-resistant strain of Escherichia coli. Eur J Biochem. 1977 Feb;72(3):613-24. doi: 10.1111/j.1432-1033.1977.tb11284.x.
Pubmed: 320005
Smith DR, Calvo JM: Nucleotide sequence of the E coli gene coding for dihydrofolate reductase. Nucleic Acids Res. 1980 May 24;8(10):2255-74. doi: 10.1093/nar/8.10.2255.
Pubmed: 6159575
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