| Revision as of 17:32, 2 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to watched fields - updated 'ChemSpiderID_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WikiProject_Pharmacology|er← Previous edit |
Latest revision as of 05:52, 2 November 2024 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,946 edits →Medical uses: wikify |
| (30 intermediate revisions by 20 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
|
{{cs1 config|name-list-style=vanc|display-authors=6}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 437150526 |
|
| verifiedrevid = 448072105 |
|
| IUPAC_name = 2-phenyl}amino)carbonyl]benzoic acid |
|
| IUPAC_name = 2-phenyl}amino)carbonyl]benzoic acid |
|
| image = phthalylsulfathiazole.png |
|
| image = Phthalylsulfathiazole.svg |
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = |
|
| tradename = |
| Line 17: |
Line 19: |
|
| legal_status = |
|
| legal_status = |
|
| routes_of_administration = |
|
| routes_of_administration = |
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!--Pharmacokinetic data--> |
|
| bioavailability = |
|
| bioavailability = |
| Line 24: |
Line 25: |
|
| elimination_half-life = |
|
| elimination_half-life = |
|
| excretion = |
|
| excretion = |
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|changed|??}} |
|
| CAS_number = |
|
| CAS_number = 85-73-4 |
|
| ATC_prefix = A07 |
|
| ATC_prefix = A07 |
|
| ATC_suffix = AB02 |
|
| ATC_suffix = AB02 |
|
| PubChem = 4806 |
|
| PubChem = 4806 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = |
|
| DrugBank = DB13248 |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 1524273 |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = 6875L5852V |
|
| UNII = 6875L5852V |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = D02440 |
|
| KEGG = D02440 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 4641 |
|
|
| smiles = C1=CC=C(C(=C1)C(=O)NC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3)C(=O)O |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 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) |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = PBMSWVPMRUJMPE-UHFFFAOYSA-N |
|
|
|
|
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=17 | H=13 | N=3 | O=5 | S=2 |
|
| C=17 | H=13 | N=3 | O=5 | S=2 |
|
| molecular_weight = 403.43222 g/mol |
|
|
}} |
|
}} |
|
|
|
|
|
|
'''Phthalylsulfathiazole''' (also known as '''sulfathalidine''')<ref>{{cite journal | vauthors = Askue WE, Tufts E | title = Phthalylsulfathiazole (sulfathalidine) in the treatment of enterobiasis (pinworm infection) | journal = The Journal of Pediatrics | volume = 44 | issue = 4 | pages = 380–385 | date = April 1954 | pmid = 13152646 | doi = 10.1016/s0022-3476(54)80210-1 }}</ref> is a sulfonamide ] used primarily for treating gastrointestinal infections.<ref name="Pubchem">{{cite web |title=Phthalylsulfathiazole |url=https://pubchem.ncbi.nlm.nih.gov/compound/Phthalylsulfathiazole |access-date=1 November 2024 |website=] |publisher=National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine }}</ref><ref name = "DrugBank">{{cite web |title=Phthalylsulfathiazole |url=https://www.drugbank.ca/drugs/DB13248 |url-status=live |archive-url=https://web.archive.org/web/20240623000716/https://go.drugbank.com/drugs/DB13248 |archive-date=23 June 2024 |access-date=1 November 2024 |work=] |publisher=University of Alberta}}</ref> |
|
'''Phthalylsulfathiazole''' belongs to the group of drugs called ]. The drug is a broad spectrum antimicrobial that can treat different types of infections including intestinal. The mechanism of action depends is based on competitive antagonism with ] and ] activity, that in turn leads to impaired synthesis of ] and as a result its active metabolite that is necessary for the synthesis of ] and ]. |
|
|
|
|
|
|
|
== Medical uses == |
|
The drug is indicated in treatment of dysentery, colitis, gastroenteritis and intestinal surgery. Adverse effects may include allergic reactions, ] insufficiency, ] and aplastic anemia. |
|
|
|
Phthalylsulfathiazole is indicated for treating various intestinal conditions, including ], ], ], and for preoperative preparation in intestinal surgery.<ref name="Pubchem" /><ref>{{cite journal | vauthors = Deng Z, Li X, Shi Y, Lu Y, Yao W, Wang J | title = A Novel Autophagy-Related IncRNAs Signature for Prognostic Prediction and Clinical Value in Patients With Pancreatic Cancer | journal = Frontiers in Cell and Developmental Biology | volume = 8 | pages = 606817 | date = 14 December 2020 | pmid = 33384999 | pmc = 7769875 | doi = 10.3389/fcell.2020.606817 | doi-access = free }}</ref> It may be administered in combination with other antimicrobials such as ], ], or ] for enhanced efficacy.<ref name = "DrugBank" /> |
|
|
|
|
|
|
Like all antibiotics, phthalylsulfathiazole should be carefully monitored to avoid promoting ].<ref name = "DrugBank" /> |
|
|
|
|
|
=== Available forms === |
|
|
Phthalylsulfathiazole is typically given orally in tablet form to target intestinal infections directly.<ref name="Pubchem" /> Due to the ] substitution on the aniline nitrogen, it remains unabsorbed in the bloodstream, focusing its action within the gut.<ref>{{cite book | vauthors = Prescott JF | chapter = Sulfonamides, Diaminopyrimidines, and Their Combinations | date = 2013-09-20 | veditors = Giguère S, Prescott JF, Dowling PM | title = Antimicrobial Therapy in Veterinary Medicine | pages = 279–294 | edition = 1st | publisher = Wiley | language = en | doi = 10.1002/9781118675014.ch17 | isbn=978-0-470-96302-9 }}</ref> |
|
|
|
|
|
== Adverse Effects == |
|
|
Common side effects include nausea, stomach upset, and skin rash.<ref>{{cite web | vauthors = Singh P | veditors = Preetha SM | title = Side effect(s) of Phthalylsulfathiazole | work = Medindia | url = https://www.medindia.net/drugs/medication-side-effects/phthalylsulfathiazole.htm }}</ref> Rare but serious adverse effects may involve ] deficiency, ], or ].<ref>{{cite journal | vauthors = Turell R, Vallecillo LA, Paradny R, Danza AL | title = Preoperative preparation of the colon with sulfonamides or antibiotics | journal = The Surgical Clinics of North America | volume = 35 | issue = Nationwide No | pages = 1211–1220 | date = October 1955 | pmid = 13267698 | doi = 10.1016/s0039-6109(16)34682-5 }}</ref> |
|
|
|
|
|
== Mechanism of action == |
|
|
Phthalylsulfathiazole acts by competitive antagonism with ], inhibiting the ] enzyme crucial for ] synthesis. This inhibition disrupts ] and ] synthesis, impairing bacterial growth and reproduction.<ref>{{cite journal | vauthors = Varenina I, Bilandžić N, Kolanović BS, Božić Đ, Sedak M, Đokić M, Varga I | title = Validation of a liquid chromatography-tandem mass spectrometry method for the simultaneous determination of sulfonamides, trimethoprim and dapsone in muscle, egg, milk and honey | journal = Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment | volume = 33 | issue = 4 | pages = 656–667 | date = 2 March 2016 | pmid = 26933907 | doi = 10.1080/19440049.2016.1152569 }}</ref> Once in the large intestine, phthalylsulfathiazole hydrolyzes to release sulfathiazole, the active antimicrobial component.<ref>{{cite book | vauthors = Rohilla S, Sharma D | chapter = Sulfonamides, quinolones, antiseptics, and disinfectants. | title = Medicinal Chemistry of Chemotherapeutic Agents | date = January 2023 | pages = 21-63 | publisher = Academic Press | doi = 10.1016/B978-0-323-90575-6.00015-6 }}</ref> |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}} |
|
{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}} |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
] |
|
|
|
|
|
|
|
|
|
{{gastrointestinal-drug-stub}} |
|
{{gastrointestinal-drug-stub}} |