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UC160

Sigma-Aldrich

4-Hydroxytolbutamide

≥98% (HPLC)

Synonym(s):

N-(Butylaminocarbonyl)-4-hydroxymethylbenzenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C12H18N2O4S
CAS Number:
5719-85-7
Molecular Weight:
286.35
MDL number:
MFCD00144466
UNSPSC Code:
12161501
PubChem Substance ID:
24724642
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

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Application

4-Hydroxytolbutamide has been used as a standard to assay the fungal biotransformation of tolbutamide to 4′-hydroxytolbutamide[1].

Packaging

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

11 - 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

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Certificates of Analysis (COA)

Lot/Batch Number
483-138-1
483-138-1V
034M3901V
034M3901
1407794V

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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
Y K Leung et al.
Journal of biochemical and biophysical methods, 36(2-3), 87-94 (1998-08-26)
A simple HPLC/fluorescence method to detect hydroxytolbutamide (a major metabolite of the anti-diabetic drug tolbutamide) has been developed. The effects of nicotine and some of its metabolites on tolbutamide hydroxylation is described. An extraction procedure with diethyl ether was followed
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