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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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
D J Back et al.
British journal of pharmacology, 81(3), 557-562 (1984-03-01)
The effects of various drugs on the pharmacokinetics of tolbutamide have been examined in the rat. Phenobarbitone pretreatment caused a significant decrease in half life and area under the curve (AUC) and a significant increase in clearance and volume of
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