Identification
- Summary
Gabexate is a protease inhibitor indicated in the treatment of acute pancreatitis.
- Generic Name
- Gabexate
- DrugBank Accession Number
- DB12831
- Background
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.4,5,6
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Gabexate (DB12831)
- Weight
- Average: 321.377
Monoisotopic: 321.168856233 - Chemical Formula
- C16H23N3O4
- Synonyms
- Gabexate
- Gabexato
- Gabexatum
Pharmacology
- Indication
No approved indication.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute pancreatitis (ap) •••••••••••• •••••••••• ••••••• ••• •••••••• Treatment of Acute pancreatitis (ap) •••••••••••• •••••••••• ••••••• ••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Gabexate bind and inhibits serine proteases in the coagulation cascade to prevent blood clotting.3 It also prevents proteolytic destruction of IkappaB resulting in suppression of the nuclear factor kappa-B signalling pathway.1 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
Gabexate inhibits kallikrein, plasmin, and thrombin by binding to their active sites.2,3 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.1 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.
Target Actions Organism APlasma kallikrein inhibitorHumans AProthrombin inhibitorHumans APlasminogen inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
LD50 of 6480mg/kg observed in rats.MSDS
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of bleeding can be increased when Abciximab is combined with Gabexate. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Gabexate. Acemetacin The risk or severity of bleeding and hemorrhage can be increased when Gabexate is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Acenocoumarol is combined with Gabexate. Acetylsalicylic acid Acetylsalicylic acid may increase the anticoagulant activities of Gabexate. - Food Interactions
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Gabexate mesylate E3Q07L0649 56974-61-9 DNTNDFLIKUKKOC-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Benzoic acid esters
- Alternative Parents
- Phenol esters / Phenoxy compounds / Benzoyl derivatives / Fatty acid esters / Dicarboxylic acids and derivatives / Guanidines / Carboxylic acid esters / Carboximidamides / Organopnictogen compounds / Organic oxides show 3 more
- Substituents
- Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carbonyl group / Carboximidamide / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Fatty acid ester / Fatty acyl show 11 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4V7M9137X9
- CAS number
- 39492-01-8
- InChI Key
- YKGYIDJEEQRWQH-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H23N3O4/c1-2-22-15(21)12-7-9-13(10-8-12)23-14(20)6-4-3-5-11-19-16(17)18/h7-10H,2-6,11H2,1H3,(H4,17,18,19)
- IUPAC Name
- ethyl 4-[(6-carbamimidamidohexanoyl)oxy]benzoate
- SMILES
- CCOC(=O)C1=CC=C(OC(=O)CCCCCNC(N)=N)C=C1
References
- General References
- Yuksel M, Okajima K, Uchiba M, Okabe H: Gabexate mesilate, a synthetic protease inhibitor, inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production by inhibiting activation of both nuclear factor-kappaB and activator protein-1 in human monocytes. J Pharmacol Exp Ther. 2003 Apr;305(1):298-305. [Article]
- Menegatti E, Bolognesi M, Scalia S, Bortolotti F, Guarneri M, Ascenzi P: Gabexate mesylate inhibition of serine proteases: thermodynamic and computer-graphics analysis. J Pharm Sci. 1986 Dec;75(12):1171-4. [Article]
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
- Brandi G, Tavolari S, De Rosa F, Di Girolamo S, Agostini V, Barbera MA, Frega G, Biasco G: Antitumoral efficacy of the protease inhibitor gabexate mesilate in colon cancer cells harbouring KRAS, BRAF and PIK3CA mutations. PLoS One. 2012;7(7):e41347. doi: 10.1371/journal.pone.0041347. Epub 2012 Jul 24. [Article]
- Xie LB, Zeng DY, Wang XD, Lin T, Li YP, Lu YP: Preconditioning with gabexate is superior to inosine for ameliorating acute renal ischemia-reperfusion injury in rats. Transplant Proc. 2014 Jan-Feb;46(1):40-5. doi: 10.1016/j.transproceed.2013.10.037. [Article]
- Kim SC, Yang HR: Clinical efficacy of gabexate mesilate for acute pancreatitis in children. Eur J Pediatr. 2013 Nov;172(11):1483-90. doi: 10.1007/s00431-013-2068-6. Epub 2013 Jun 29. [Article]
- AIFA Product Information: Gabexate mesylate powder for solution for infusion [Link]
- External Links
- PubChem Compound
- 3447
- PubChem Substance
- 347828997
- ChemSpider
- 3329
- BindingDB
- 50104435
- ChEBI
- 93036
- ChEMBL
- CHEMBL87563
- ZINC
- ZINC000002002226
- Wikipedia
- Gabexate
- MSDS
- Download (79.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Terminated Supportive Care Liver Disease 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder, for solution Intravenous 100 MG Powder, for solution Intravenous 100 MG/5ML - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.109 mg/mL ALOGPS logP 1.83 ALOGPS logP 2.1 Chemaxon logS -3.5 ALOGPS pKa (Strongest Basic) 12.13 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 114.5 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 96.7 m3·mol-1 Chemaxon Polarizability 35.67 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 180.89796 predictedDeepCCS 1.0 (2019) [M+H]+ 183.25597 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.34923 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type endopeptidase activity
- Specific Function
- The enzyme cleaves Lys-Arg and Arg-Ser bonds. It activates, in a reciprocal reaction, factor XII after its binding to a negatively charged surface. It also releases bradykinin from HMW kininogen an...
- Gene Name
- KLKB1
- Uniprot ID
- P03952
- Uniprot Name
- Plasma kallikrein
- Molecular Weight
- 71369.205 Da
References
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Thrombospondin receptor activity
- Specific Function
- Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostas...
- Gene Name
- F2
- Uniprot ID
- P00734
- Uniprot Name
- Prothrombin
- Molecular Weight
- 70036.295 Da
References
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type peptidase activity
- Specific Function
- Plasmin dissolves the fibrin of blood clots and acts as a proteolytic factor in a variety of other processes including embryonic development, tissue remodeling, tumor invasion, and inflammation. In...
- Gene Name
- PLG
- Uniprot ID
- P00747
- Uniprot Name
- Plasminogen
- Molecular Weight
- 90568.415 Da
References
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Serine-type endopeptidase activity
- Specific Function
- Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
- Gene Name
- PRSS1
- Uniprot ID
- P07477
- Uniprot Name
- Trypsin-1
- Molecular Weight
- 26557.88 Da
References
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Serine-type endopeptidase activity
- Specific Function
- C1s B chain is a serine protease that combines with C1q and C1r to form C1, the first component of the classical pathway of the complement system. C1r activates C1s so that it can, in turn, activat...
- Gene Name
- C1S
- Uniprot ID
- P09871
- Uniprot Name
- Complement C1s subcomponent
- Molecular Weight
- 76683.905 Da
References
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Serine-type peptidase activity
- Specific Function
- C1r B chain is a serine protease that combines with C1q and C1s to form C1, the first component of the classical pathway of the complement system.
- Gene Name
- C1R
- Uniprot ID
- P00736
- Uniprot Name
- Complement C1r subcomponent
- Molecular Weight
- 80118.04 Da
References
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
Drug created at October 21, 2016 00:33 / Updated at June 12, 2021 10:54