UC160
4-Hydroxytolbutamide
≥98% (HPLC)
Synonym(s):
N-(Butylaminocarbonyl)-4-hydroxymethylbenzenesulfonamide
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About This Item
Empirical Formula (Hill Notation):
C12H18N2O4S
CAS Number:
Molecular Weight:
286.35
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12161501
MDL number:
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)
SMILES string
CCCCNC(=O)NS(=O)(=O)c1ccc(CO)cc1
InChI key
SJRHYONYKZIRPM-UHFFFAOYSA-N
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
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.
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.
Other Notes
Metabolite of tolbutamide; formed by the cytochrome CYP2CIIC8 and IIC9 subfamily of P450 enzymes.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Biotransformation of tolbutamide to 4'-hydroxytolbutamide by the fungus Cunninghamella blakesleeana.
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
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
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
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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