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Phthalylsulfathiazole

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Chemical compound

Pharmaceutical compound
Phthalylsulfathiazole
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 2-[({4-[(1,3-Thiazol-2-ylamino)sulfonyl]phenyl}amino)carbonyl]benzoic acid
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.480Edit this at Wikidata
Chemical and physical data
FormulaC17H13N3O5S2
Molar mass403.43 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) ☒N
  • Key:PBMSWVPMRUJMPE-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Phthalylsulfathiazole (also known assulfathalidine)[1] is a sulfonamidebroad-spectrum antimicrobial used primarily for treating gastrointestinal infections.[2][3]

Medical uses

[edit]

Phthalylsulfathiazole is indicated for treating various intestinal conditions, includingdysentery,colitis,gastroenteritis, and for preoperative preparation in intestinal surgery.[2][4] It may be administered in combination with other antimicrobials such asmetronidazole,furazolidone, orneomycin for enhanced efficacy.[3]

Like all antibiotics, phthalylsulfathiazole should be carefully monitored to avoid promotingbacterial resistance.[3]

Available forms

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Phthalylsulfathiazole is typically given orally in tablet form to target intestinal infections directly.[2] Due to thephthalic acid substitution on the aniline nitrogen, it remains unabsorbed in the bloodstream, focusing its action within the gut.[5]

Adverse Effects

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Common side effects include nausea, stomach upset, and skin rash.[6] Rare but serious adverse effects may involvevitamin B deficiency,agranulocytosis, oraplastic anemia.[7]

Mechanism of action

[edit]

Phthalylsulfathiazole acts by competitive antagonism withpara-aminobenzoic acid, inhibiting thedihydropteroate synthetase enzyme crucial fordihydrofolic acid synthesis. This inhibition disruptspurine andpyrimidine synthesis, impairing bacterial growth and reproduction.[8] Once in the large intestine, phthalylsulfathiazole hydrolyzes to release sulfathiazole, the active antimicrobial component.[9]

References

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  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. ^abc"Phthalylsulfathiazole".PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. Retrieved1 November 2024.
  3. ^abc"Phthalylsulfathiazole".DrugBank. University of Alberta.Archived from the original on 23 June 2024. Retrieved1 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.
Rehydration
Intestinal anti-infectives
Intestinaladsorbents
Antipropulsives (opioids)
Intestinal anti-inflammatory agents
Antidiarrheal micro-organisms
Other antidiarrheals
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