Chemical Properties
White Solid
Uses
Labelled Tolazamide, an antidiabetic.
Definition
ChEBI: An N-sulfonylurea that is 1-tosylurea in which a hydrogen attached to the nitrogen at position 3 is replaced by an azepan-1-yl group. A hypoglycemic agent, it is used for the treatment of type 2 diabetes mellitus.
General Description
Tolazamide is N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide; or 1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; or 1-(4-methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea (generic).Tolazamide incorporates a fully saturated azepine moietythat is but weakly basic, with a pKa of～3.32 The pKa of thesulfonylurea group lies within the typical range; thus, inareas of the duodenum wherein the pH falls within the rangeof 4 to 5, the uncharged form of the drug is the predominantspecies, and its lipophilicity lends to rapid absorption bypassive diffusion.
General Description
Tolazamide, 1-(hexahydro-1Hazepin-1-yl)-3-(p-tolylsulfonyl)urea (Tolinase), is an analogof tolbutamide and is reported to be effective, in general,under the same circumstances in which tolbutamide is useful.Tolazamide, however, appears to be more potent than tolbutamideand is nearly equal in potency to chlorpropamide. Instudies with radioactive tolazamide, investigators found that85% of an oral dose appeared in the urine as metabolites thatwere more soluble than tolazamide itself.
General Description
White to off-white crystalline powder. Odorless or with a slight odor.
Air & Water Reactions
TOLAZAMIDE may be sensitive to prolonged exposure to air. Insoluble in water.
Reactivity Profile
TOLAZAMIDE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). TOLAZAMIDE is incompatible with acids. .
Fire Hazard
Flash point data for TOLAZAMIDE are not available; however, TOLAZAMIDE is probably combustible.
China
