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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:
5719-85-7
Molecular Weight:
286.35
NACRES:
NA.77
PubChem Substance ID:
24724642
UNSPSC Code:
12161501
MDL number:
MFCD00144466
Assay:
≥98% (HPLC)
Form:
solid
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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

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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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)
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
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
View All Related Papers

Global Trade Item Number

SKUGTIN
UC160-10MG04061837410161
UC160-5MG04061837410178