Basic information
- CAS
85-73-4- Standard SMILES
O=C(O)c1ccccc1C(=O)Nc1ccc(S(=O)(=O)Nc2nccs2)cc1- InChIKey
PBMSWVPMRUJMPE-UHFFFAOYSA-N- Molecular formula
- C17H13N3O5S2
- Average molar mass
- 403.4 g/mol
- Monoisotopic mass
- 403.02966287
Overview
Phthalylsulfathiazole is a sulfonamide incorporating 2-carboxybenzamido and 1,3-thiazol-2-yl moieties that is a broad-spectrum antibiotic indicated in the treatment of dysentery, colitis, gastroenteritis and intestinal surgery. It is a sulfonamide, a dicarboxylic acid monoamide, a member of 1,3-thiazoles and a sulfonamide antibiotic. It is functionally related to a phthalic acid.
Names & identifiers
- Preferred name
- Phthalylsulfathiazole
- IUPAC
- 2-[[4-(1,3-thiazol-2-ylsulfamoyl)phenyl]carbamoyl]benzoic acid
- English name
- Phthalylsulfathiazole
- Molecular formula
- C17H13N3O5S2
- Molecular weight
- 403.43
Names & synonyms
phthalylsulfathiazole85-73-4SulfathalidinePhthalazolPhthalylsulphathiazolePhthalylsulfonazoleSulphaphthalylSulfaphthalazolePhthalylnorsulfazoleThalazoleFtalazolPhtalylsulfathiazol
Show more names
PSTPhthalysulfathiazoleN4-PHTHALYLSULFATHIAZOLEST1A1SIAT8DTSPST1ST8SIA4TalidineThalinil
PhthalazolumFtalilsulfatiazolPhthalylsulfathiazolum4'-(2-Thiazolylsulfamoyl)phthalanilic acidDTXSID8023470NSC-66454NSC-683525CHEBI:9336
Database identifiers
- CAS
85-73-4- PubChem CID
- 4806
- DTXSID
DTXSID8023470- ChEMBL
CHEMBL1524273- ChEBI
CHEBI:9336- UNII
- 6875L5852V
- EC Number
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 162 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 643
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Human DrugsPharmaceuticals
Collision Cross Section
188.63 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
194.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 198 · 198-204°C
- Boiling point
- 371.31 ℃[at · 371.31℃[at 101 325 Pa]
- Density
- 1.4235 · 1.4235 (rough estimate)
- vapor pressure
- 0 Pa · 0Pa at 25℃
- refractive index
- 1.639 · 1.6390 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Practically insoluble in water, freely soluble in dimethylformamide, slightly soluble in acetone and in ethanol (96 per cent).
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
H412 (33.3%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
REACH registered substance: Phthalylsulfathiazole (EC: 201-627-4)
Phthalylsulfathiazole: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Benzoic acid, 2-[[[4-[(2-thiazolylamino)sulfonyl]phenyl]amino]carbonyl]-: Environment tier I assessment
Hazard Classes and CategoriesAquatic Chronic 3 (33.3%)
Safety data
- wgk
- WGK 3
- tsca
- TSCA listed
- rtecs
- TH8575000
- ridadr
- 3249
- hs_code
- 29350090
- Toxicity
- LD50 i.p. in mice: 920 mg/kg (Mattis)
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08,GHS09
- safety_code
- 24/25
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Mechanism of ActionPhthalylsulfathiazole is a prodrug: Once administered, phthalylsulfathiazole releases its active metabolite, sulfathiazole, which targets the bacterial folate synthesis pathway by inhibiting the dihydropteroate synthase enzyme.
Uses & manufacturing
Use ClassificationPharmaceuticals
General Manufacturing InformationBenzoic acid, 2-[[[4-[(2-thiazolylamino)sulfonyl]phenyl]amino]carbonyl]-: INACTIVE
Applications
UsesPhthalylsulfathiazole is a sulfonamide antibacterial drug with similar and stronger effects than Sulfaguanidine and Succinylsulfathiazole. It is rarely absorbed orally and slowly decomposes in the intestine to release Sulfathiazole and exert intestinal antibacterial effects, and is used in the treatment of dysentery, colitis, and gastroenteritis.
Preparation methods
PreparationIt may be prepared by the interaction of sulfathiazole and phthalic anhydride in equimolar proportions.It exerts its bacteriostatic effect in the gastro-intestinal tract. It has been found to be twice as active as sulfaguanidine in the treatment of bowel irregularities. It is often effective in watery diarrhoeas and ulcerative colitis. It is also used in the pre-operative treatment of patients undergoing surgery of the intestinal tract. It may also be recommended in the treatment of acute bascillary dysentry of the Sonne, Flexner and Shiga species.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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