Chemistry:Phthalylsulfathiazole
Phthalylsulfathiazole (also known as sulfathalidine)[1] is a sulfonamide broad-spectrum antimicrobial used primarily for treating gastrointestinal infections.[2][3]
Medical uses
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
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
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
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
- ↑ "Phthalylsulfathiazole (sulfathalidine) in the treatment of enterobiasis (pinworm infection)". The Journal of Pediatrics 44 (4): 380–385. April 1954. doi:10.1016/s0022-3476(54)80210-1. PMID 13152646.
- ↑ 2.0 2.1 2.2 "Phthalylsulfathiazole". National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/Phthalylsulfathiazole.
- ↑ 3.0 3.1 3.2 "Phthalylsulfathiazole". DrugBank. University of Alberta. https://www.drugbank.ca/drugs/DB13248.
- ↑ "A Novel Autophagy-Related IncRNAs Signature for Prognostic Prediction and Clinical Value in Patients With Pancreatic Cancer". Frontiers in Cell and Developmental Biology 8. 14 December 2020. doi:10.3389/fcell.2020.606817. PMID 33384999.
- ↑ "Sulfonamides, Diaminopyrimidines, and Their Combinations" (in en). Antimicrobial Therapy in Veterinary Medicine (1st ed.). Wiley. 2013-09-20. pp. 279–294. doi:10.1002/9781118675014.ch17. ISBN 978-0-470-96302-9.
- ↑ "Side effect(s) of Phthalylsulfathiazole". Medindia. https://www.medindia.net/drugs/medication-side-effects/phthalylsulfathiazole.htm.
- ↑ "Preoperative preparation of the colon with sulfonamides or antibiotics". The Surgical Clinics of North America 35 (Nationwide No): 1211–1220. October 1955. doi:10.1016/s0039-6109(16)34682-5. PMID 13267698.
- ↑ "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. 2 March 2016. doi:10.1080/19440049.2016.1152569. PMID 26933907.
- ↑ "Sulfonamides, quinolones, antiseptics, and disinfectants.". Medicinal Chemistry of Chemotherapeutic Agents. Academic Press. January 2023. pp. 21-63. doi:10.1016/B978-0-323-90575-6.00015-6.
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