3-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)propanoic acid

• ChemBase ID: 102766
• Molecular Formular: C13H13N3O5S2
• Molecular Mass: 355.38942
• Monoisotopic Mass: 355.02966253
• SMILES: OC(=O)CCC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• Canonical SMILES: O=C(Nc1ccc(cc1)S(=O)(=O)Nc1nccs1)CCC(=O)O
• InChI: InChI=1S/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)
• InChIKey: SKVLYVHULOWXTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)propanoic acid
• IUPAC Traditional name: 3-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)propanoic acid; succinylsulfathiazole
• Synonyms: Succinylsulfathiazole; Succinylsulphathiazole; Kaoxidin; Sulfasuxidine; Colistatin; SUCCINYLSULFATHIAZOLE

Database IDs

• CAS Number: 116-43-8
• EC Number: 204-141-0
• MDL Number: MFCD00022437
• Beilstein Number: 349989
• PubChem SID: 24899811; 162090073
• PubChem CID: 5315

CALCULATED PROPERTIES

• Acid pKa: 3.3619187
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.2780585
• LogD (pH = 7.4): -3.0957887
• Log P: 0.866527
• Molar Refractivity: 83.3282 cm^3
• Polarizability: 32.270557 Å^3
• Polar Surface Area: 125.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: WM4767000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Mechanism of Action: Dihydrofolate reductase inhibitor; Dihydrofolate synthesis inhibitor;; Folate antagonist

Product Information

• Purity: ≥99%
• Application(s): Antidiarrheic; Antiseptic; Intestinal antibacterial agent

DETAILS

MP Biomedicals - 02102976

Crystalline

Sigma Aldrich - S8752

Application
Succinylsulfathiazole is used to block the synthesis of folic acid. It is used to study folate deficiency1. It is used to suppress folate production by bacteria in the intestine2.
Biochem/physiol Actions
Succinylsulfathiazole is a competitive inhibitor of dihydropteroate synthetase. It is a dihydrofolate reductase (DHFR) inhibitor.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S8752.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Poth, E.J. et al., Arch. Surg. (Chicago), 1942, 44, 187-222, (pharmacol)
• Moore, M.L. et al., J.A.C.S., 1942, 64, 1572-1576, (synth)
• U.S. Pat., 1944, Sharp and Dohme, 2 324 013; CA, 38, 2193, (synth)
• Phillips, M.A., Chem. Ind. (London), 1945, 247, (synth)
• Kram, T.C., J. Pharm. Sci., 1972, 61, 254, (hplc)
• Moustafa, M.A. et al., J. Pharm. Sci., 1974, 63, 1103-1109, (polymorph)
• Chang, C.J. et al., J. Med. Chem., 1975, 18, 505, (nmr)
• Rodier, N. et al., Acta Cryst. B, 1978, 34, 218-221, (cryst struct)
• Burger, A. et al., Sci. Pharm., 1989, 57, 293-305, (polymorph, struct, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 204
• Bourne, S.A. et al., J. Pharm. Sci., 1994, 83, 887-892, (cryst struct solvates)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 3391