Gabexate
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Gabexate
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CAS No:
39492-01-8
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Formula:
C16H23N3O4
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Chemical Name:
Gabexate
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Synonyms:
Benzoic acid,4-[[6-[(aminoiminomethyl)amino]-1-oxohexyl]oxy]-,ethyl ester;p-Carbethoxyphenyl ε-guanidinocaproate;Gabexate;p-Carbethoxyphenyl ε-guanidineocaproate
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CAS No:
Description
4-[6-(diaminomethylideneamino)-1-oxohexoxy]benzoic acid ethyl ester is a benzoate ester.|Gabexate is a synthetic serine protease inhibitor which has been used as an anticoagulant. It also known to decrease production of inflammatory cytokines. Gabexate has been investigated for use in cancer, ischemia-reperfusion injury, and pancreatitis.|A serine proteinase inhibitor used therapeutically in the treatment of pancreatitis, disseminated intravascular coagulation (DIC), and as a regional anticoagulant for hemodialysis. The drug inhibits the hydrolytic effects of thrombin, plasmin, and kallikrein, but not of chymotrypsin and aprotinin.
Drug Information
No approved indication.
Gabexate bind and inhibits serine proteases in the coagulation cascade to prevent blood clotting. It also prevents proteolytic destruction of IkappaB resulting in suppression of the nuclear factor kappa-B signalling pathway. Ultimately this decreases the production of inflammatory cytokines such as tumor necrosis factor alpha which are produced as a result of NFkappaB activation.
Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES. (See all compounds classified as Serine Proteinase Inhibitors.)|Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)
Gabexate inhibits kallikrein, plasmin, and thrombin by binding to their active sites. The inhibition of these components of the coagulation cascade ultimately prevents the formation of fibrin which must be present and polymerized to form a clot. Gabexate decreases the production of inflammatory cytokines by attenuating NFkappaB and c-Jun N-terminal kinase (JNK) pathway activity. The exact mechanism for this is unknown but it is thought that gabexate prevents the proteolyytic destruction of IkappaB which deactivates NFkappaB and interferes with activator protein 1 binding to DNA.
Foy
Computed Properties
Molecular Weight:321.37
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:11
Exact Mass:321.16885622
Monoisotopic Mass:321.16885622
Topological Polar Surface Area:117
Heavy Atom Count:23
Complexity:400
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes