4-{[(butylcarbamoyl)amino]sulfonyl}benzoic acid

• ChemBase ID: 154330
• Molecular Formular: C12H16N2O5S
• Molecular Mass: 300.33084
• Monoisotopic Mass: 300.07799262
• SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C(=O)O
• Canonical SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C(=O)O
• InChI: InChI=1S/C12H16N2O5S/c1-2-3-8-13-12(17)14-20(18,19)10-6-4-9(5-7-10)11(15)16/h4-7H,2-3,8H2,1H3,(H,15,16)(H2,13,14,17)
• InChIKey: GCMVATDSSHTCOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(butylcarbamoyl)amino]sulfonyl}benzoic acid
• IUPAC Traditional name: 4-[(butylcarbamoyl)aminosulfonyl]benzoic acid
• Synonyms: 4-[[[(Butylamino)carbonyl]amino]sulfonyl]-benzoic Acid; p-[(Butylcarbamoyl)sulfamoyl]-benzoic Acid; Tolbutamide Carboxylic Acid; 1-Butyl-3-(p-carboxyphenyl)sulfonylurea; Carboxycarbutamide; 4-Carboxy Tolbutamide; N-Butyl-N′-(4-carboxyphenylsulfonyl)urea; Carboxytolbutamide

Database IDs

• CAS Number: 2224-10-4
• MDL Number: MFCD00272697
• PubChem SID: 162248469
• PubChem CID: 159651

CALCULATED PROPERTIES

• Acid pKa: 3.453933
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.292202
• LogD (pH = 7.4): -2.8651283
• Log P: 1.4394974
• Molar Refractivity: 72.485 cm^3
• Polarizability: 28.47792 Å^3
• Polar Surface Area: 112.57 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: white; White to Off-White Solid
• Melting Point: >300°C (dec.); 210-212 °C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C12H16N2O5S

DETAILS

Sigma Aldrich - UC260

Biochem/physiol Actions
In vivo tolbutamide metabolite. Major urinary metabolite of tolbutamide.

Toronto Research Chemicals - C183200

A metabolite of Tolbutamide. Formed by the cytochrome CYP2CIIC8 and IIC9 subfamily of P450 enzymes.

REFERENCES

• Relling, et al.: J. Pharmacol. Exp. Ther., 252, 442 (1990)
• Parent, et al.: J. Pharmacol. Exp. Ther., 261, 780 (1990)
• Ho, et al.: Life Sci., 52, 21 (1990)