CAS 116-43-8|3-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)propanoic acid|SUCCINYLSULFATHIAZOLE|succinylsulfathiazole|Succinylsulfathiazole|Colistatin|Sulfasuxidine|Kaoxidin|3-({4-[(1,3-thiazo...

General Information

Structure

Molecular Formula

C₁₃H₁₃N₃O₅S₂

Molecular Mass

355.38942

Exact Mass

355.02966253

Charge

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

Canonic Smiles

O=C(Nc1ccc(cc1)S(=O)(=O)Nc1nccs1)CCC(=O)O

Isomeric Smiles

OC(=O)CCC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1nccs1

Calculated Properties

JChem

Acid pKa

3.3619187

H Acceptors

H Donor

LogD (pH = 5.5)

-1.2780585

LogD (pH = 7.4)

-3.0957887

Log P

0.866527

Molar Refractivity

83.3282

Polarizability

32.270557

Polar Surface Area

125.46

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

SUCCINYLSULFATHIAZOLESuccinylsulfathiazoleColistatinSulfasuxidineKaoxidinSuccinylsulphathiazole

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

CAS Number

EC Number

PubChem SID

MDL Number

Beilstein Number

PubChem CID

Registration numbers

Properties

Product Information

Pharmacology Properties

Mechanism of Action

Dihydrofolate reductase inhibitor

Folate antagonist

Dihydrofolate synthesis inhibitor;

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

Molecule Details

References

PubChem Literature

From Data Sources

• Kram, T.C., J. Pharm. Sci., 1972, 61, 254, (hplc)

• Poth, E.J. et al., Arch. Surg. (Chicago), 1942, 44, 187-222, (pharmacol)

• 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

• Rodier, N. et al., Acta Cryst. B, 1978, 34, 218-221, (cryst struct)

• Moore, M.L. et al., J.A.C.S., 1942, 64, 1572-1576, (synth)

• Burger, A. et al., Sci. Pharm., 1989, 57, 293-305, (polymorph, struct, props)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 204

• Chang, C.J. et al., J. Med. Chem., 1975, 18, 505, (nmr)

• U.S. Pat., 1944, Sharp and Dohme, 2 324 013; CA, 38, 2193, (synth)

• Phillips, M.A., Chem. Ind. (London), 1945, 247, (synth)

• Moustafa, M.A. et al., J. Pharm. Sci., 1974, 63, 1103-1109, (polymorph)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

IUPAC name

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

Synonyms

SUCCINYLSULFATHIAZOLESuccinylsulfathiazoleColistatinSulfasuxidineKaoxidinSuccinylsulphathiazole

IUPAC Traditional name

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

Registration numbers

CAS Number

EC Number

PubChem SID

MDL Number

Beilstein Number

PubChem CID

Properties

Product Information

Pharmacology Properties

Mechanism of Action

Dihydrofolate reductase inhibitor

Folate antagonist

Dihydrofolate synthesis inhibitor;

Molecule Details

MP Biomedicals

02102976

Crystalline

Sigma Aldrich

S8752

References

PubChem Literature

From Data Sources

• Kram, T.C., J. Pharm. Sci., 1972, 61, 254, (hplc)

• Poth, E.J. et al., Arch. Surg. (Chicago), 1942, 44, 187-222, (pharmacol)

• 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

• Rodier, N. et al., Acta Cryst. B, 1978, 34, 218-221, (cryst struct)

• Moore, M.L. et al., J.A.C.S., 1942, 64, 1572-1576, (synth)

• Burger, A. et al., Sci. Pharm., 1989, 57, 293-305, (polymorph, struct, props)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 204

• Chang, C.J. et al., J. Med. Chem., 1975, 18, 505, (nmr)

• U.S. Pat., 1944, Sharp and Dohme, 2 324 013; CA, 38, 2193, (synth)

• Phillips, M.A., Chem. Ind. (London), 1945, 247, (synth)

• Moustafa, M.A. et al., J. Pharm. Sci., 1974, 63, 1103-1109, (polymorph)

Bioactivity

PubChem BioAssay

Molecule

ID:102766