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Phthalylsulfathiazole

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A07AB02 (WHO)
Identifiers
IUPAC name 2-phenyl}amino)carbonyl]benzoic acid
CAS Number	85-73-4
PubChem CID	4806
DrugBank	DB13248
ChemSpider	4641
UNII	6875L5852V
KEGG	D02440
ChEMBL	ChEMBL1524273
CompTox Dashboard (EPA)	DTXSID8023470
ECHA InfoCard	100.001.480
Chemical and physical data
Formula	C17H13N3O5S2
Molar mass	403.43 g·mol
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C(=C1)C(=O)NC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3)C(=O)O
InChI 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) Key:PBMSWVPMRUJMPE-UHFFFAOYSA-N
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Phthalylsulfathiazole (also known as sulfathalidine) is a sulfonamide broad-spectrum antimicrobial used primarily for treating gastrointestinal infections.

Medical uses

Phthalylsulfathiazole is indicated for treating various intestinal conditions, including dysentery, colitis, gastroenteritis, and for preoperative preparation in intestinal surgery. It may be administered in combination with other antimicrobials such as metronidazole, furazolidone, or neomycin for enhanced efficacy.

Like all antibiotics, phthalylsulfathiazole should be carefully monitored to avoid promoting bacterial resistance.

Available forms

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

Adverse Effects

Common side effects include nausea, stomach upset, and skin rash. Rare but serious adverse effects may involve vitamin B deficiency, agranulocytosis, or aplastic anemia.

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. Once in the large intestine, phthalylsulfathiazole hydrolyzes to release sulfathiazole, the active antimicrobial component.

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. ^ "Phthalylsulfathiazole". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. Retrieved 1 November 2024.
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.

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