2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole

• ChemBase ID: 1000
• Molecular Formular: C18H21N3O3S
• Molecular Mass: 359.44264
• Monoisotopic Mass: 359.13036255
• SMILES: S(=O)(Cc1nccc(OCCCOC)c1C)c1[nH]c2c(n1)cccc2
• Canonical SMILES: COCCCOc1ccnc(c1C)CS(=O)c1nc2c([nH]1)cccc2
• InChI: InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)
• InChIKey: YREYEVIYCVEVJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• IUPAC Traditional name: rabeprazole; 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• Brand Name: AcipHex; Pariet
• Synonyms: 2-(((4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole; Irsogladine Maleate; Rebeprazole sodium; rabeprazole sodium; Rabeprazole

Database IDs

• CAS Number: 117976-89-3
• MDL Number: MFCD00868879
• PubChem SID: 160964463; 46506366
• PubChem CID: 5029

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.346711
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0682993
• LogD (pH = 7.4): 2.0861723
• Log P: 2.0907433
• Molar Refractivity: 98.0668 cm^3
• Polarizability: 39.284637 Å^3
• Polar Surface Area: 77.1 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.04
• LOG S: -3.03
• Solubility (Water): 3.36e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.6

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB01129

• Drug Groups: approved; investigational
• Description: Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. It is a prodrug - in the acid environment of the parietal cells it turns into active sulphenamide form. Rabeprazole inhibits the H+, K+ATPase of the coating gastric cells and dose-dependent oppresses basal and stimulated gastric acid secretion.
• Indication: For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
• Pharmacology: Rabeprazole prevents the production of acid in the stomach. It reduces symptoms and prevents injury to the esophagus or stomach in patients with gastroesophageal reflux disease (GERD) or ulcers. Rabeprazole is also useful in conditions that produce too much stomach acid such as Zollinger-Ellison syndrome. Rabeprazole may also be used with antibiotics to get rid of bacteria that are associated with some ulcers. Rabeprazole is a selective and irreversible proton pump inhibitor, suppresses gastric acid secretion by specific inhibition of the H^+, K^+ -ATPase, which is found at the secretory surface of parietal cells. In doing so, it inhibits the final transport of hydrogen ions (via exchange with potassium ions) into the gastric lumen.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absolute bioavailability is approximately 52%.
• Half Life: 1-2 hours (in plasma)
• Protein Binding: 96.3% (bound to human plasma proteins)
• Elimination: Following a single 20 mg oral dose of 14C-labeled rabeprazole, approximately 90% of the drug was eliminated in the urine, primarily as thioether carboxylic acid; its glucuronide, and mercapturic acid metabolites.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com