39492-01-8

Gabexate Mesylate,Shangai Lansheng

Gabexate mesylate is used in combination with somatostatin and octreotide in the treatment of severe acute pancreatitis in elderly patients.

ChEBI: 4-[6-(diaminomethylideneamino)-1-oxohexoxy]benzoic acid ethyl ester is a benzoate ester.

Guanidinocaproic acid p-tosyl salt and thionyl chloride were mixed together to react at the room temperature. An endothermic reaction occurred and the caproic acid gradually dissolved. Then the reaction mixture was left standing for 1 to 2 h and was extracted with ether. The lower oily layer and the ether layer were separated from each other and the lower layer was repeatedly washed with ether. Then the oily substance (caproic acid chloride) was added with benzoic acid ethyl ester in tetrahydrofuran, and the mixture was stirred. After the mixture became a uniform solution, of pyridine were gradually added. An exothermic reaction occurred and an oily substance came to be separated in the lower layer. After the completion of the reaction, the oily substance was washed with water and then recrystallized from hot water once or twice. Thus 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester salt was obtained as white crystals.
To obtained the base 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester the 4-(6-guanidino-hexanoyloxy)-benzoic acid ethyl ester salt must be treated by, for example, sodium hydroxide.
In practice it is usually used as mesylate.

Enzyme inhibitor

Serine protease inhibitor; inhibits trypsin, plasmin, plasma kallikrein and thrombin (IC 50 values are 9.4, 30, 41 and 110 mM respectively). Antithrombotic in vitro and in vivo . Also inhibits LPS-induced TNF- α production, probably by inhibiting NF- κ B and AP-1 activation.