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Gabexate

HCID 3447
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
39492-01-8
Standard SMILES
CCOC(=O)c1ccc(OC(=O)CCCCCN=C(N)N)cc1
InChIKey
YKGYIDJEEQRWQH-UHFFFAOYSA-N
Molecular formula
C16H23N3O4
Average molar mass
321.37 g/mol
Monoisotopic mass
321.16885622

Overview

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

Names & identifiers

Preferred name
Gabexate
IUPAC
ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate
English name
GABEXATE
Molecular formula
C16H23N3O4
Molecular weight
321.37

Names & synonyms

gabexate39492-01-8GabexatoGabexatumethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoateEthyl p-hydroxybenzoate 6-guanidinohexanoate4V7M9137X9DTXSID9048566Benzoic acid, 4-((6-((aminoiminomethyl)amino)-1-oxohexyl)oxy)-, ethyl esterethyl 4-(6-(diaminomethylideneamino)hexanoyloxy)benzoateMesilate, GabexateMesylate, Gabexate
Show more names
Gabexate USP/EP/BPGabexateMesylateBase4-[(6-Guanidinohexanoyl)oxy]benzoic acid ethyl esterdiaminomethylidene-[6-(4-ethoxycarbonylphenoxy)-6-oxohexyl]ammonium4-[[6-[[Amino(imino)methyl]amino]-1-oxohexyl]oxy]benzoic acid ethyl esterBenzoic acid, 4-[[6-[(aminoiminomethyl)amino]-1-oxohexyl]oxy]-, ethylester[N'-[5-(4-ethoxycarbonylphenoxy)carbonylpentyl]carbamimidoyl]azanium methanesulfonate
RefChem:142027Methanesulfonate, GabexateMonomethanesulfonate, GabexateDTXCID2028195Gabexate Monomethanesulfonate, 14C Labeled Cpdethyl 4-((6-carbamimidamidohexanoyl)oxy)benzoateGabexate [INN]CHEMBL87563

Database identifiers

CAS
39492-01-8
PubChem CID
3447
DTXSID
DTXSID9048566
ChEMBL
CHEMBL87563
ChEBI
CHEBI:93036
UNII
4V7M9137X9
Nikkaji
J22.697A

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
117 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
11
Heavy atoms
23
Formal charge
0
Complexity
400

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Boiling point
472.2 · 472.2±55.0 °C(Predicted)
Density
1.2 · 1.20±0.1 g/cm3(Predicted)
storage temp.
Desiccate at RT
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
13.83 · 13.83±0.70(Predicted)
color
White
FDA UNII
4 V7M9137X9 · 4V7M9137X9

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Gabexate

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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.

MeSH Pharmacological Classification · 2 items

Agents that prevent BLOOD CLOTTING.

Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES.

Applications

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

Upstream & downstream products

Upstream raw materials

Sodium hydroxideEthyl benzoateThionyl chloridePyridine

Suppliers12 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Sinoway Industrial co., ltd.+86-0592-5800732 +86-13806035118 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]

Additional notes

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

Related reactions

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Compound notes

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