| Identification | More | [Name]
p-2-Thiazolylsulfamoylsuccinanilic acid | [CAS]
116-43-8 | [Synonyms]
2-(n(4)-succinylsulfanilamido)thiazole
2-(N-SUCCINYLSULFANILAMIDO)THIAZOLE
4'-(2-THIAZOLYLSULFAMOYL)-SUCCINANILIC ACID
colistatin
cremosuxidine
kaoxidin
KAOXIDINE
p-2-thiazolylsulfamoylsuccinanilic acid
rolsul
SST
SUCCINYLSULFATHIAZOLE
SULFASUXIDINE
SULFENTERONE
THIACYL
4’-(2-thiazolylsulfamoyl)-succinanilicaci
4-oxo-4-((4-((2-thiazolylamino)sulfonyl)phenyl)amino)-butanoicaci
succinylsulphathiazole
sulfadigesin
sulfasuccidin
sulfasuccidine | [EINECS(EC#)]
204-141-0 | [Molecular Formula]
C13H13N3O5S2 | [MDL Number]
MFCD00022437 | [Molecular Weight]
355.39 | [MOL File]
116-43-8.mol |
| Questions And Answer | Back Directory | [Synthesis]
The production of succinylsulfathiazole typically involves the condensation of succinic anhydride and sulfathiazole in a dry organic solvent, with a yield of approximately 92%. Hydrophilic solvents are preferred. Succinylsulfathiazole can also be synthesized in a solid-phase manner, still using succinic anhydride and sulfathiazole as starting materials. Solid-phase synthesis is significantly better than solvent condensation. Its advantages include: 1. No organic solvent required; 2. Simple equipment and easy operation; 3. Safe; 4. High yield and low cost; 5. Small difference in the ratio of succinic anhydride to sulfathiazole in the starting materials. The preparation reaction formula is shown in the figure below: 
Figure 1 Preparation reaction formula of succinylsulfathiazole |
| Chemical Properties | Back Directory | [Melting point ]
193.5°C | [density ]
1.4807 (rough estimate) | [refractive index ]
1.6390 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
1 M NaOH: soluble50mg/mL | [form ]
powder | [pka]
pKa 4.5 (Uncertain) | [color ]
white to off-white | [Water Solubility ]
0.49g/L(38 ºC) | [λmax]
282nm(H2O (pH 3.3 - 5))(lit.) | [Merck ]
8877 | [BRN ]
349989 | [CAS DataBase Reference]
116-43-8(CAS DataBase Reference) | [EPA Substance Registry System]
116-43-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
3249 | [WGK Germany ]
3
| [RTECS ]
WM4767000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29350090 |
| Hazard Information | Back Directory | [Originator]
Sulfasuxidine,MSD,US,1942 | [Uses]
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. | [Uses]
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. | [Uses]
Succinylsulfathiazole is antibacterial
| [Definition]
ChEBI: N-succinylsulfathiazole is a member of 1,3-thiazoles. It is functionally related to a sulfathiazole. | [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) | [storage]
Store at -20°C | [References]
[1] Pharmaceutical Chemistry Journal, 1997, vol. 31, # 9, p. 471 - 473
[2] Patent: US2007/292352, 2007, A1. Location in patent: Page/Page column 45
[3] Patent: US2324013, 1941,
[4] Journal of the American Chemical Society, 1942, vol. 64, p. 1572,1573, 1574
[5] Patent: US2324014, 1941, |
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