Phthalylsulfathiazole
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| ECHA InfoCard | 100.001.480 |
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| Formula | C17H13N3O5S2 |
| Molar mass | 403.43 g·mol−1 |
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Phthalylsulfathiazole (also known as sulfathalidine)[1] is a sulfonamide broad-spectrum antimicrobial used primarily for treating gastrointestinal infections.[2][3]
Medical uses
[edit]Phthalylsulfathiazole is indicated for treating various intestinal conditions, including dysentery, colitis, gastroenteritis, and for preoperative preparation in intestinal surgery.[2][4] It may be administered in combination with other antimicrobials such as metronidazole, furazolidone, or neomycin for enhanced efficacy.[3]
Like all antibiotics, phthalylsulfathiazole should be carefully monitored to avoid promoting bacterial resistance.[3]
Available forms
[edit]Phthalylsulfathiazole is typically given orally in tablet form to target intestinal infections directly.[2] Due to the phthalic acid substitution on the aniline nitrogen, it remains unabsorbed in the bloodstream, focusing its action within the gut.[5]
Adverse Effects
[edit]Common side effects include nausea, stomach upset, and skin rash.[6] Rare but serious adverse effects may involve vitamin B deficiency, agranulocytosis, or aplastic anemia.[7]
Mechanism of action
[edit]Phthalylsulfathiazole acts by competitive antagonism with para-aminobenzoic acid, inhibiting the dihydropteroate synthetase enzyme crucial for dihydrofolic acid synthesis. This inhibition disrupts purine and pyrimidine synthesis, impairing bacterial growth and reproduction.[8] Once in the large intestine, phthalylsulfathiazole hydrolyzes to release sulfathiazole, the active antimicrobial component.[9]
References
[edit]- ^ Askue WE, Tufts E (April 1954). "Phthalylsulfathiazole (sulfathalidine) in the treatment of enterobiasis (pinworm infection)". The Journal of Pediatrics. 44 (4): 380–385. doi:10.1016/s0022-3476(54)80210-1. PMID 13152646.
- ^ a b c "Phthalylsulfathiazole". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. Retrieved 1 November 2024.
- ^ a b c "Phthalylsulfathiazole". DrugBank. University of Alberta. Archived from the original on 23 June 2024. Retrieved 1 November 2024.
- ^ Deng Z, Li X, Shi Y, Lu Y, Yao W, Wang J (14 December 2020). "A Novel Autophagy-Related IncRNAs Signature for Prognostic Prediction and Clinical Value in Patients With Pancreatic Cancer". Frontiers in Cell and Developmental Biology. 8: 606817. doi:10.3389/fcell.2020.606817. PMC 7769875. PMID 33384999.
- ^ Prescott JF (2013-09-20). "Sulfonamides, Diaminopyrimidines, and Their Combinations". In Giguère S, Prescott JF, Dowling PM (eds.). Antimicrobial Therapy in Veterinary Medicine (1st ed.). Wiley. pp. 279–294. doi:10.1002/9781118675014.ch17. ISBN 978-0-470-96302-9.
- ^ Singh P. Preetha SM (ed.). "Side effect(s) of Phthalylsulfathiazole". Medindia.
- ^ Turell R, Vallecillo LA, Paradny R, Danza AL (October 1955). "Preoperative preparation of the colon with sulfonamides or antibiotics". The Surgical Clinics of North America. 35 (Nationwide No): 1211–1220. doi:10.1016/s0039-6109(16)34682-5. PMID 13267698.
- ^ Varenina I, Bilandžić N, Kolanović BS, Božić Đ, Sedak M, Đokić M, et al. (2 March 2016). "Validation of a liquid chromatography-tandem mass spectrometry method for the simultaneous determination of sulfonamides, trimethoprim and dapsone in muscle, egg, milk and honey". Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment. 33 (4): 656–667. doi:10.1080/19440049.2016.1152569. PMID 26933907.
- ^ Rohilla S, Sharma D (January 2023). "Sulfonamides, quinolones, antiseptics, and disinfectants.". Medicinal Chemistry of Chemotherapeutic Agents. Academic Press. pp. 21–63. doi:10.1016/B978-0-323-90575-6.00015-6.
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