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Merck
CN

46968

Tolbutamide

VETRANAL®, analytical standard

Synonym(s):

1-Butyl-3-(4-methylphenylsulfonyl)urea, N-[(Butylamino)carbonyl]-4-methylbenzenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C12H18N2O3S
CAS Number:
64-77-7
Molecular Weight:
270.35
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329757278
EC Number:
200-594-3
Beilstein/REAXYS Number:
1984428
MDL number:
MFCD00027169

Key Documents

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InChI key

JLRGJRBPOGGCBT-UHFFFAOYSA-N

InChI

1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

SMILES string

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

grade

analytical standard

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

clinical testing

format

neat

Quality Level

200

Gene Information

human ... ABCC8(6833), KCNJ1(3758), KCNJ11(3767)

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Anti-diabetic agent. Metabolized by CYP2C9 (tolbutamide hydroxylase).

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF4700
BCBV8457

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Kevin S C Hamming et al.
Diabetes, 59(7), 1686-1693 (2010-04-24)
The sodium-calcium exchanger isoform 1 (NCX1) regulates cytoplasmic calcium (Ca(2+)(c)) required for insulin secretion in beta-cells. NCX1 is alternatively spliced, resulting in the expression of splice variants in different tissues such as NCX1.3 and -1.7 in beta-cells. As pharmacological inhibitors
Yasinalli Tamboli et al.
Bioorganic & medicinal chemistry letters, 22(11), 3810-3815 (2012-05-09)
We describe a new class of NO-donor hypoglycemic products obtained by joining tolbutamide, a typical hypoglycemic sulfonylurea, with a NO-donor moiety through a hard link. As NO-donors we chose either furoxan (1,2,5-oxadiazole 2-oxide) derivatives or the classical nitrooxy function. A
Ruurdtje Hoekstra et al.
Drug metabolism and disposition: the biological fate of chemicals, 41(3), 562-567 (2012-12-15)
The human liver cell line HepaRG has been recognized as a promising source for in vitro testing of metabolism and toxicity of compounds. However, currently the hepatic differentiation of these cells relies on exposure to dimethylsulfoxide (DMSO), which, as a
Claire E Hills et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 30(3), 575-586 (2012-07-27)
The extracellular calcium-sensing receptor (CaR) is expressed in pancreatic β-cells where it is thought to facilitate cell-to-cell communication and augment insulin secretion. However, it is unknown how CaR activation improves β-cell function. Immunocytochemistry and western blotting confirmed the expression of
Genetic factors influencing the metabolism of tolbutamide.
D J Back et al.
Pharmacology & therapeutics, 44(2), 147-155 (1989-01-01)
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