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T2408

Sigma-Aldrich

Tolazamide

Synonym(s):

1-(Hexahydro-1H-azepin-1-yl)-3-(p-toluenesulfonyl)urea

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About This Item

Empirical Formula (Hill Notation):
C14H21N3O3S
CAS Number:
1156-19-0
Molecular Weight:
311.40
EC Number:
214-588-3
MDL number:
MFCD00083504
UNSPSC Code:
12352200
PubChem Substance ID:
24277741

solubility

0.1 M NaOH: soluble 4.3 mg/ml
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble 2.7 mg/ml
DMSO: soluble 32.5 mg/ml
acetone: soluble 50 mg/ml, clear, colorless to light yellow

SMILES string

Cc1ccc(cc1)S(=O)(=O)NC(=O)NN2CCCCCC2

InChI

1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)

InChI key

OUDSBRTVNLOZBN-UHFFFAOYSA-N

Gene Information

human ... ALB(213) , KCNJ1(3758)

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Application

Tolazamide has been used as a KATP channel inhibitor to study changes in mean arterial blood pressure (MAP) in rat models of severe hemorrhagic shock2.

Biochem/physiol Actions

Stimulates pancreatic islet cells to secrete insulin; blocks ATP-sensitive K+ channels.

Preparation Note

Tolazamide is soluble in acetone at 50 mg/ml and yields a clear, colorless to light yellow solution. Furthermore, tolazamide is soluble in DMSO at 32.5 mg/ml, in 0.1 N NaOH at 4.3 mg/ml and in 45% (w/v)aqueous 2-hyroxypropyl-β-cyclodextrin at 2.7 mg/ml. It is insoluble in water.

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
SLBD0732V
SLBB6397V
110M1735V
110M1735
050M1278

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B L True et al.
The American journal of psychiatry, 144(9), 1220-1221 (1987-09-01)
Cases of profound hypoglycemia after the initiation of tricyclic antidepressant therapy in two patients taking sulfonylureas are described. To the authors' knowledge, this is the first report of a potential drug interaction between tricyclic antidepressants and sulfonylureas.
J A Pugh et al.
Diabetes care, 15(8), 953-959 (1992-08-01)
To assess the efficacy of combination therapy with insulin and sulfonylurea in the treatment of NIDDM. Studies published between January 1966 and January 1991 were identified through a computerized Medline search and by hand searching the bibliographies of identified articles.
C Szabó et al.
Shock (Augusta, Ga.), 5(6), 391-394 (1996-06-01)
Potassium channels closed by increases in intracellular ATP levels (KATP channels) have been described in vascular smooth muscle cells and other cell types. These channels are responsive to the metabolic state of the cells, and can be opened by a
P H Wang et al.
The Journal of clinical investigation, 84(1), 62-67 (1989-07-01)
The extrapancreatic actions of sulfonylureas on the glucose transport system were studied in the L6 line of cultured rat skeletal muscle cells. Insulin (10(-7) M) increased 2-deoxyglucose uptake in differentiated L6 myotubes by 30-40% after 8 h of incubation. The
S Heffelfinger et al.
Human pathology, 18(7), 751-754 (1987-07-01)
A unique hepatic adenoma developed in a 26-year-old woman who had used oral contraceptives for 10 years and Tolinase (tolazamide sulfonylurea) for adult-onset diabetes mellitus for five years. Clinically, radiographically, and grossly, the neoplasm showed the usual features of a
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