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

• ChemBase编号: 1000
• 分子式: C18H21N3O3S
• 平均质量: 359.44264
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• IUPAC传统名: rabeprazole; 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• 商标名: AcipHex; Pariet
• 别名: 2-(((4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole; Irsogladine Maleate; Rebeprazole sodium; rabeprazole sodium; Rabeprazole

登记号

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

理论计算性质

JChem

• Acid pKa: 9.346711
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 2.0682993
• LogD (pH = 7.4): 2.0861723
• Log P: 2.0907433
• 摩尔折射率: 98.0668 cm^3
• 极化性: 39.284637 Å^3
• 极化表面积: 77.1 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.04
• LOG S: -3.03
• 溶解度: 3.36e-01 g/l

分子性质

理化性质

• 疏水性(logP): 0.6

产品相关信息

• 纯度: 95+%

详细说明

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