116-43-8

Basic information

• Product Name: p-2-Thiazolylsulfamoylsuccinanilic acid
• Synonyms: colistatin;cremosuxidine;kaoxidin;KAOXIDINE;2-(n(4)-succinylsulfanilamido)thiazole;2-(N-SUCCINYLSULFANILAMIDO)THIAZOLE;4'-(2-THIAZOLYLSULFAMOYL)-SUCCINANILIC ACID;THIACYL
• CAS NO: 116-43-8
• Molecular Formula: C₁₃H₁₃N₃O₅S₂
• Molecular Weight: 355.39
• EINECS: 204-141-0
• Product Categories: Antibiotics for Research and Experimental Use;Biochemistry;Sulfonamides (Antibiotics for Research and Experimental Use);Antibacterial;Antibiotics;Antibiotics A to;Antibiotics N-SAntibiotics;Chemical Structure Class;Inhibits an EnzymeAntibiotics;Interferes with DNA SynthesisSpectrum of Activity;L - ZAntibiotics;Mechanism of Action;Sulfonamides;SULFASUXIDINE
• Mol File: 116-43-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 193.5°C
• Appearance: white to off-white/
• Density: 1.4807 (rough estimate)
• Refractive Index: 1.6390 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: 1 M NaOH: soluble50mg/mL
• PKA: pKa 4.5 (Uncertain)
• Water Solubility: 0.49g/L(38 oC)
• Merck: 14,8877
• BRN: 349989
• CAS DataBase Reference: p-2-Thiazolylsulfamoylsuccinanilic acid(CAS DataBase Reference)
• NIST Chemistry Reference: p-2-Thiazolylsulfamoylsuccinanilic acid(116-43-8)
• EPA Substance Registry System: p-2-Thiazolylsulfamoylsuccinanilic acid(116-43-8)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-36/37-45
• RIDADR: 3249
• WGK Germany: 3
• RTECS: WM4767000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 116-43-8(Hazardous Substances Data)

Usage

Originator

Sulfasuxidine,MSD,US,1942

Uses

Different sources of media describe the Uses of 116-43-8 differently. You can refer to the following data:
1. Succinylsulfathiazole is antibacterial
2. Succinylsulfathiazole is a sulfonamide antibiotic that was shown to inhibit bacteria that are responsible for folate production. Succinylsulfathiazole was used in various folate deficiency studies to block the synthesis of folic acid.
3. Succinylsulfathiazole is a sulfonamide antibiotic that was shown to inhibit bacteria that are responsible for folate production. Succinylsulfathiazole was used in various folate deficiency studies to block the synthesis of folic acid.

Manufacturing Process

3.92 g of succinic anhydride was added to a boiling suspension of 10 g of 2- sulfanilamidothiazole in 100 cc of alcohol. The mixture was then refluxed for five minutes after the addition was complete at which time all of the solids were in solution. The solution was then cooled and diluted with an equal volume of water. The white solid precipitate which formed was filtered and recrystallized from dilute alcohol, yielding 2-N4-succinylsulfanilamidothiazole, melting at 184°C to 186°C.

Therapeutic Function

Antibacterial (intestinal)

InChI:InChI=1/C13H13N3O5S2/c17-11(5-6-12(18)19)15-9-1-3-10(4-2-9)23(20,21)16-13-14-7-8-22-13/h1-4,7-8H,5-6H2,(H,14,16)(H,15,17)(H,18,19)

Upstream product

• 72-14-0 Sulfathiazole 
• 36340-57-5 N,N-succinyl-sulfanilic acid thiazol-2-ylamide 
• 108-30-5 succinic acid anhydride 
• 96-50-4 2-thiazolylamine 
• 5694-39-3 N-(4-chlorosulfonyl-phenyl)-succinamic acid 
• 110-15-6 succinic acid 

Downstream Products

• 485-47-2 indan-1,2,3-trione hydrate 
• 14945-45-0 N-[4-(3-xanthen-9-yl-3H-thiazol-2-ylidenesulfamoyl)-phenyl]-succinamic acid 
• 36340-57-5 N,N-succinyl-sulfanilic acid thiazol-2-ylamide 
• 1429036-21-4 C₁₇H₁₆N₄O₇S₂ 

Relevant articles and documents

X-ray structural studies and physicochemical characterization of the 1- butanol, 1-pentanol, and 1,4-dioxane solvates of succinylsulfathiazole

The crystal structures and thermal decomposition of three solvated forms of the antibacterial drug succinylsulfathiazole (SST) have been studied. The solvates, with 1:1 host-guest stoichiometry, are SST-1-butanol (1) SST-1- pentanol (2), and SST-1,4-dioxane (3). Solvates 1 and 2 crystallize in the triclinic system, space group P1, with two formula units per cell, and are nearly isostructural. The OH groups of the guest molecules in both solvates engage in hydrogen bonding to the host SST and occupy cavities in the crystals. Solvate 3 is triclinic, space group P1, with two formula units per cell, but the two independent solvent molecules are located in crystallographically distinct channels. In one channel, solvent molecules are hydrogen bonded to the host while, in the other, they are held by van der Waals interactions only. The structural results are in accord with thermogravimetric and differential scanning calorimetric data which indicate one-step desolvation for 1 and 2 but two-step desolvation for 3. X-ray powder diffraction was used to attempt identification of the polymorphic forms of SST resulting from desolvation of 1-3. Desolvation of 1 and 3 appears to yield pure polymorphs of SST while 2 yields a mixture of polymorphs. The activation energies for the desolvation of the nearly isomorphous solvates 1 and 2 were found by dynamic thermogravimetry to be 155 and 149 kJ mol-1, respectively.

Synthesis and antiviral activity of N[p-(R-sulfamoyl)phenyl]succinamic acids and their salts with 2-amino-2-thiazoline

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