MilliporeSigma
All Photos(1)

UC160

Sigma-Aldrich

4-Hydroxytolbutamide

≥98% (HPLC)

Synonym(s):
N-(Butylaminocarbonyl)-4-hydroxymethylbenzenesulfonamide
Empirical Formula (Hill Notation):
C12H18N2O4S
CAS Number:
Molecular Weight:
286.35
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

color

white

mp

100-102 °C

solubility

ethanol: soluble 12 mg/mL
0.1 M NaOH: soluble 4 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

CCCCNC(=O)NS(=O)(=O)c1ccc(CO)cc1

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)

InChI key

SJRHYONYKZIRPM-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

4-Hydroxytolbutamide has been used as a standard to assay the fungal biotransformation of tolbutamide to 4′-hydroxytolbutamide.

Packaging

5, 10 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

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

Preparation Note

4-Hydroxytolbutamide is soluble in ethanol at 12 mg/mL and is also soluble in 0.1 M NaOH at 4 mg/ml. It is insoluble in water.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Use of tolbutamide as a substrate probe for human hepatic cytochrome P450 2C9.
J O Miners et al.
Methods in enzymology, 272, 139-145 (1996-01-01)
Alexander Jetter et al.
European journal of clinical pharmacology, 60(3), 165-171 (2004-03-27)
The hypoglycaemic drug tolbutamide is used for assessment of CYP2C9 activity in vivo. However, therapeutically active doses of 500 mg bear the risk of hypoglycaemia, and a tolbutamide-derived parameter based on a single plasma or urine concentration reflecting CYP2C9 activity
Haihua Huang et al.
Applied microbiology and biotechnology, 72(3), 486-491 (2006-02-24)
The hypoglycemic drug tolbutamide is commonly used as a probe drug to evaluate CYP2C9 enzyme activity in terms of production of 4'-hydroxytolbutamide. In the present study, an initial screening of seven filamentous fungi was carried out to identify which was
Ji-Hong Shon et al.
Pharmacogenetics, 12(2), 111-119 (2002-03-05)
Several recent in-vitro data have revealed that CYP2C19, in addition to CYP2C9, is also involved in the 4-methylhydroxylation of tolbutamide. We evaluated the relative contribution of CYP2C9 and CYP2C19 genetic polymorphisms on the disposition of blood glucose lowering response to
Julia Kirchheiner et al.
Pharmacogenetics, 12(2), 101-109 (2002-03-05)
Tolbutamide is known to be metabolized by cytochrome P450 2C9 (CYP2C9), and the effects of the CYP2C9 amino acid polymorphisms *2 (Arg144Cys) and *3 (Ile359Leu) could be important for drug treatment with tolbutamide and for use of tolbutamide as a

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service