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UC260

Sigma-Aldrich

Carboxytolbutamide

Synonym(s):

N-Butyl-N´-(4-carboxyphenylsulfonyl)urea

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About This Item

Empirical Formula (Hill Notation):
C12H16N2O5S
CAS Number:
2224-10-4
Molecular Weight:
300.33
MDL number:
MFCD00272697
UNSPSC Code:
12161501
PubChem Substance ID:
329827662
NACRES:
NA.77

form

solid

color

white

mp

210-212 °C

solubility

methanol: soluble

storage temp.

2-8°C

SMILES string

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

InChI

1S/C12H16N2O5S/c1-2-3-8-13-12(17)14-20(18,19)10-6-4-9(5-7-10)11(15)16/h4-7H,2-3,8H2,1H3,(H,15,16)(H2,13,14,17)

InChI key

GCMVATDSSHTCOS-UHFFFAOYSA-N

Application

Carboxytolbutamide has been used as a standard to determine tolbutamide metabolites in urine samples[1].

Biochem/physiol Actions

In vivo tolbutamide metabolite. Major urinary metabolite of tolbutamide.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

Carboxytolbutamide is soluble in methanol.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
496-009-1V
1396561V
496-009-1
1396561
085K1359

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E W Cate et al.
Journal of clinical pharmacology, 26(5), 372-377 (1986-05-01)
This study was designed to compare the effects of equivalent therapeutic doses of two H2 antagonists, cimetidine and ranitidine, on tolbutamide pharmacokinetics. Twelve healthy men were given a 1-g oral dose of tolbutamide on three occasions. Subjects were randomly assigned
G A Cook
The Journal of biological chemistry, 262(11), 4968-4972 (1987-04-15)
The hypoglycemic sulfonylureas glyburide and tolbutamide were found to be excellent inhibitors of the rat liver, heart, and skeletal muscle carnitine palmitoyltransferases, but glyburide was by far the most potent inhibitor. Carboxytolbutamide, a sulfonylurea that has no hypoglycemic effect, produced
M A Bruce et al.
Drug metabolism and disposition: the biological fate of chemicals, 29(7), 1023-1028 (2001-06-16)
The in vivo effects of oral clarithromycin administration on the in vivo activity of cytochrome P450 1A2, 2C9, and 2D6 were determined. The cytochrome P450 probes caffeine (CYP1A2), tolbutamide (CYP2C9), and dextromethorphan (CYP2D6) were administered as an oral cocktail prior
G Raghow et al.
Journal of pharmaceutical sciences, 70(10), 1166-1168 (1981-10-01)
A high-performance liquid chromatographic method was developed for the simultaneous measurement of tolbutamide and its major metabolite, carboxytolbutamide, in plasma. The assay involves the ether extraction of 1 ml of plasma, using chlorpropamide and an internal standard. The extract is
T Y Nelson et al.
The Journal of biological chemistry, 262(6), 2608-2612 (1987-02-25)
The mechanisms by which glyburide and tolbutamide signal insulin secretion were examined using a beta cell line (Hamster insulin-secreting tumor (HIT) cells). Insulin secretion was measured in static incubations, free cytosolic Ca2+ concentration ([Ca2+]i) was monitored in quin 2-loaded cells
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