Phthalylsulfathiazole

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Phthalylsulfathiazole
Phthalylsulfathiazole.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • 2-[({4-[(1,3-Thiazol-2-ylamino)sulfonyl]phenyl}amino)carbonyl]benzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.480 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H13N3O5S2
Molar mass 403.43 g·mol−1
3D model (JSmol)
  • C1=CC=C(C(=C1)C(=O)NC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3)C(=O)O
  • InChI=1S/C17H13N3O5S2/c21-15(13-3-1-2-4-14(13)16(22)23)19-11-5-7-12(8-6-11)27(24,25)20-17-18-9-10-26-17/h1-10H,(H,18,20)(H,19,21)(H,22,23) X mark.svgN
  • Key:PBMSWVPMRUJMPE-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Phthalylsulfathiazole (also known as sulfathalidine) [1] is a sulfonamide broad-spectrum antimicrobial used primarily for treating gastrointestinal infections. [2] [3]

Contents

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

  1. 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.
  2. 1 2 3 "Phthalylsulfathiazole". PubChem . National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. Retrieved 1 November 2024.
  3. 1 2 3 "Phthalylsulfathiazole". DrugBank . University of Alberta. Archived from the original on 23 June 2024. Retrieved 1 November 2024.
  4. 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.
  5. 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.
  6. Singh P. Preetha SM (ed.). "Side effect(s) of Phthalylsulfathiazole". Medindia.
  7. 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.
  8. 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.
  9. 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.