3-butyl-1-[4-(hydroxymethyl)benzenesulfonyl]urea

• ChemBase ID: 132829
• Molecular Formular: C12H18N2O4S
• Molecular Mass: 286.34732
• Monoisotopic Mass: 286.09872807
• SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)CO
• Canonical SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)CO
• InChI: InChI=1S/C12H18N2O4S/c1-2-3-8-13-12(16)14-19(17,18)11-6-4-10(9-15)5-7-11/h4-7,15H,2-3,8-9H2,1H3,(H2,13,14,16)
• InChIKey: SJRHYONYKZIRPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-butyl-1-[4-(hydroxymethyl)benzenesulfonyl]urea
• IUPAC Traditional name: hydroxytolbutamide
• Synonyms: N-(Butylaminocarbonyl)-4-hydroxymethylbenzenesulfonamide; N-(Butylamnocarbonyl)-4-hydroxymethylbenzenesulfonamide; Hydroxytolbutamide; Hydroxymethylcarbutamide; 1-Butyl-3-(p-hydroxymethylphenyl)sulfonylurea; Hydroxy Tolbutamide; 4-Hydroxytolbutamide; N-(丁基氨基甲酰)-4-羟甲基苯磺酰胺; 4-羟基甲苯磺丁脲

Database IDs

• CAS Number: 5719-85-7
• MDL Number: MFCD00144466
• PubChem SID: 24724642; 162227106
• PubChem CID: 3656

CALCULATED PROPERTIES

• Acid pKa: 4.3286376
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.24496257
• LogD (pH = 7.4): 0.07447111
• Log P: 1.0145646
• Molar Refractivity: 72.0447 cm^3
• Polarizability: 28.535568 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble4 mg/mL; DMSO; ethanol: soluble12 mg/mL; H2O: insoluble; Methanol
• Apperance: white; White Solid
• Melting Point: 100-102 °C; 101-103°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H18N2O4S

DETAILS

Sigma Aldrich - T145

Other Notes
甲苯磺丁脲的代谢物；通过 P450 酶的细胞色素 CYP2CIIC8 和 IIC9 亚家族形成。

Sigma Aldrich - UC160

Other Notes
Metabolite of tolbutamide; formed by the cytochrome CYP2CIIC8 and IIC9 subfamily of P450 enzymes.

Toronto Research Chemicals - H969850

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

REFERENCES

• Relling, etl 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)