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Identification
NameEcabet
Accession NumberDB05265
TypeSmall Molecule
GroupsApproved, Investigational
Description

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.

Structure
Thumb
Synonyms
Ecabet
Ecabet sodium
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
GastromTanabe Mitsubishi, Japan
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ecabet sodium
86408-72-2
Thumb
  • InChI Key: RCVIHORGZULVTN-YGJXXQMASA-M
  • Monoisotopic Mass: 402.14768942
  • Average Mass: 402.48
DBSALT000062
Categories
UNII2K02669KWP
CAS number33159-27-2
WeightAverage: 380.498
Monoisotopic: 380.165744696
Chemical FormulaC20H28O5S
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Abietane diterpenoid
  • Phenanthrene
  • Hydrophenanthrene
  • Tetralin
  • 1-sulfo,2-unsubstituted aromatic compound
  • Cumene
  • Arylsulfonic acid or derivatives
  • Benzenoid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of reflux oesophagitis and peptic ulcer disease.
PharmacodynamicsNot Available
Mechanism of actionEcabet 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9357
Blood Brain Barrier+0.8758
Caco-2 permeable-0.63
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8403
P-glycoprotein inhibitor IINon-inhibitor0.7504
Renal organic cation transporterNon-inhibitor0.8911
CYP450 2C9 substrateNon-substrate0.6979
CYP450 2D6 substrateNon-substrate0.8179
CYP450 3A4 substrateSubstrate0.5303
CYP450 1A2 substrateNon-inhibitor0.7918
CYP450 2C9 inhibitorNon-inhibitor0.8472
CYP450 2D6 inhibitorNon-inhibitor0.9023
CYP450 2C19 inhibitorNon-inhibitor0.718
CYP450 3A4 inhibitorNon-inhibitor0.8145
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9109
Ames testNon AMES toxic0.6719
CarcinogenicityCarcinogens 0.6053
BiodegradationNot ready biodegradable0.9876
Rat acute toxicity2.3482 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9382
hERG inhibition (predictor II)Non-inhibitor0.588
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00426 mg/mLALOGPS
logP1.5ALOGPS
logP4.93ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.07 m3·mol-1ChemAxon
Polarizability41.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Shinji Narisawa, “Aqueous ecabet sodium solution preparation.” U.S. Patent US20040259905, issued December 23, 2004.

US20040259905
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 the perception of gravity. Isoform 3 is more potent than isoform 1 in activating NOX3. Together with NOXA1, may also substitute to NCF1/p47phox and NCF2/p67phox in supporting the phagocyte NOX2/gp91ph...
Gene Name:
NOXO1
Uniprot ID:
Q8NFA2
Molecular Weight:
41252.315 Da
References
  1. 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. [PubMed:15458921 ]
Kind
Protein
Organism
Enterobacter aerogenes
Pharmacological action
yes
Actions
inhibitor
General Function:
Urease activity
Specific Function:
Not Available
Gene Name:
ureC
Uniprot ID:
P18314
Molecular Weight:
60304.12 Da
References
  1. 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. [PubMed:12749277 ]
  2. Takahashi S, Tanaka A: [Ecabet sodium]. Nihon Rinsho. 2002 Feb;60 Suppl 2:711-6. [PubMed:11979876 ]
  3. 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. [PubMed:11472321 ]
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Drug created on November 18, 2007 11:22 / Updated on May 16, 2016 11:07