Ecabet
Identification
- Generic Name
- Ecabet
- DrugBank Accession Number
- DB05265
- Background
Ecabet is a prescription eye drop for the treatment of dry eye syndrome. Ecabet represents a new class of molecules that increases the quantity and quality of mucin produced by conjunctival goblet cells and corneal epithelia. Mucin is a glycoprotein component of tear film that lubricates while retarding moisture loss from tear evaporation. Ecabet is currently marketed in Japan as an oral agent for treatment of gastric ulcers and gastritis.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 380.498
Monoisotopic: 380.165744696 - Chemical Formula
- C20H28O5S
- Synonyms
- Ecabet
- Ecabetum
Pharmacology
- Indication
For the treatment of reflux oesophagitis and peptic ulcer disease.
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- Pharmacodynamics
Not Available
- Mechanism of action
Ecabet reduces the survival of H. pylori in the stomach and inhibits pepsin activity in the gastric juice of experimental animals. Here we have investigated the effects of ecabet on some of the factors involved in the dynamics of the mucosal barrier, i.e. pepsins and mucins. Pepsin, acid and Helicobacter pylori are major factors in the pathophysiology of peptic ulcer disease and reflux oesophagitis. Ecabet also acts as an inhibitor of H. pylori NADPH oxidase as well as urease. Inhibition of these enzymes prevents bacterial adhesion to gastric mucosa.
Target Actions Organism AUrease subunit alpha inhibitorEnterobacter aerogenes ANADPH oxidase organizer 1 antagonistHumans - 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
Not Available
- 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 softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Ecabet is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Ecabet is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Ecabet is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Ecabet is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Ecabet is combined with Bupivacaine. - Food Interactions
- Not Available
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 Ecabet sodium 51MO2B2OSB 86408-72-2 RCVIHORGZULVTN-YGJXXQMASA-M - International/Other Brands
- Gastrom (Tanabe Mitsubishi, Japan)
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Diterpenoids
- Direct Parent
- Diterpenoids
- Alternative Parents
- Hydrophenanthrenes / Tetralins / 1-sulfo,2-unsubstituted aromatic compounds / Sulfonyls / Organosulfonic acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 1-sulfo,2-unsubstituted aromatic compound / Abietane diterpenoid / Aromatic homopolycyclic compound / Arylsulfonic acid or derivatives / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Diterpenoid / Hydrocarbon derivative
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 2K02669KWP
- CAS number
- 33159-27-2
- InChI Key
- IWCWQNVIUXZOMJ-MISYRCLQSA-N
- InChI
- InChI=1S/C20H28O5S/c1-12(2)14-10-13-6-7-17-19(3,8-5-9-20(17,4)18(21)22)15(13)11-16(14)26(23,24)25/h10-12,17H,5-9H2,1-4H3,(H,21,22)(H,23,24,25)/t17-,19-,20-/m1/s1
- IUPAC Name
- (1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-6-sulfo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
- SMILES
- [H][C@@]12CCC3=CC(C(C)C)=C(C=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)S(O)(=O)=O
References
- Synthesis Reference
Shinji Narisawa, "Aqueous ecabet sodium solution preparation." U.S. Patent US20040259905, issued December 23, 2004.
US20040259905- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015613
- KEGG Drug
- D07885
- PubChem Compound
- 65781
- PubChem Substance
- 99443230
- ChemSpider
- 59201
- ChEBI
- 135593
- ChEMBL
- CHEMBL2104585
- ZINC
- ZINC000003779720
- PharmGKB
- PA165958350
- Drugs.com
- Drugs.com Drug Page
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 4 Unknown Status Treatment Delayed Bleeding / Quality of Ulcer / Ulcer Healing 1 2 Completed Treatment Dry Eye Syndrome (DES) 2 2, 3 Completed Treatment Dry Eye Syndrome (DES) 1 Not Available Completed Treatment Gastro-esophageal Reflux Disease (GERD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00426 mg/mL ALOGPS logP 1.5 ALOGPS logP 4.93 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) -1.5 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 91.67 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 100.07 m3·mol-1 Chemaxon Polarizability 41.24 Å3 Chemaxon Number of Rings 3 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
Property Value Probability Human Intestinal Absorption + 0.9357 Blood Brain Barrier + 0.8758 Caco-2 permeable - 0.63 P-glycoprotein substrate Substrate 0.5 P-glycoprotein inhibitor I Non-inhibitor 0.8403 P-glycoprotein inhibitor II Non-inhibitor 0.7504 Renal organic cation transporter Non-inhibitor 0.8911 CYP450 2C9 substrate Non-substrate 0.6979 CYP450 2D6 substrate Non-substrate 0.8179 CYP450 3A4 substrate Substrate 0.5303 CYP450 1A2 substrate Non-inhibitor 0.7918 CYP450 2C9 inhibitor Non-inhibitor 0.8472 CYP450 2D6 inhibitor Non-inhibitor 0.9023 CYP450 2C19 inhibitor Non-inhibitor 0.718 CYP450 3A4 inhibitor Non-inhibitor 0.8145 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9109 Ames test Non AMES toxic 0.6719 Carcinogenicity Carcinogens 0.6053 Biodegradation Not ready biodegradable 0.9876 Rat acute toxicity 2.3482 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9382 hERG inhibition (predictor II) Non-inhibitor 0.588
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0i2c-0098000000-8616f99fe7bf5b6d3cf2 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001r-0009000000-5e3a702af1b10f5e9b80 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-faf3d7c2eece323705ec Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f8l-0079000000-7ebf07431783488e5784 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-c3becaba557535fc8523 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-8291000000-8ffaba93f374e19367dc Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0091000000-a34ec9484e7d582880f4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.6552978 predictedDarkChem Lite v0.1.0 [M-H]- 193.37985 predictedDeepCCS 1.0 (2019) [M+H]+ 195.73784 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.71994 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Enterobacter aerogenes
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Urease activity
- Specific Function
- Not Available
- Gene Name
- ureC
- Uniprot ID
- P18314
- Uniprot Name
- Urease subunit alpha
- Molecular Weight
- 60304.12 Da
References
- Koizumi W, Tanabe S, Imaizumi H, Kida M, Ohida M, Koshida Y, Mitomi H, Hosaka Y, Nagaba S, Sasaki T, Higuchi K, Saigenji K: Inhibition of peptic ulcer relapse by ranitidine and ecabet independently of eradication of Helicobacter pylori: a prospective, controlled study versus ranitidine. Hepatogastroenterology. 2003 Mar-Apr;50(50):577-81. [Article]
- Takahashi S, Tanaka A: [Ecabet sodium]. Nihon Rinsho. 2002 Feb;60 Suppl 2:711-6. [Article]
- Adachi K, Ishihara S, Hashimoto T, Hirakawa K, Ishimura N, Niigaki M, Kaji T, Kawamura A, Sato H, Fujishiro H, Hattori S, Watanabe M, Kinoshita Y: Efficacy of ecabet sodium for Helicobacter pylori eradication triple therapy in comparison with a lansoprazole-based regimen. Aliment Pharmacol Ther. 2001 Aug;15(8):1187-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Superoxide-generating nadph oxidase activator activity
- Specific Function
- Constitutively potentiates the superoxide-generating activity of NOX1 and NOX3 and is required for the biogenesis of otoconia/otolith, which are crystalline structures of the inner ear involved in ...
- Gene Name
- NOXO1
- Uniprot ID
- Q8NFA2
- Uniprot Name
- NADPH oxidase organizer 1
- Molecular Weight
- 41252.315 Da
References
- Kusumoto K, Kawahara T, Kuwano Y, Teshima-Kondo S, Morita K, Kishi K, Rokutan K: Ecabet sodium inhibits Helicobacter pylori lipopolysaccharide-induced activation of NADPH oxidase 1 or apoptosis of guinea pig gastric mucosal cells. Am J Physiol Gastrointest Liver Physiol. 2005 Feb;288(2):G300-7. Epub 2004 Sep 30. [Article]
Drug created at November 18, 2007 18:22 / Updated at January 02, 2024 23:47