Phthalylsulfathiazole

Phthalylsulfathiazole
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A07AB02 (WHO) ;
Identifiers
	IUPAC name 2-[({4-[(1,3-Thiazol-2-ylamino)sulfonyl]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−1
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)^[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

^ 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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[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.

[Pubchem-2] "Phthalylsulfathiazole". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. Retrieved 1 November 2024.

[DrugBank-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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