2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole

• ChemBase编号: 331
• 分子式: C16H14F3N3O2S
• 平均质量: 369.3614696
• 单一同位素质量: 369.07588236
• SMILES: S(=O)(Cc1nccc(OCC(F)(F)F)c1C)c1[nH]c2c(n1)cccc2
• Canonical SMILES: O=S(c1nc2c([nH]1)cccc2)Cc1nccc(c1C)OCC(F)(F)F
• InChI: InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)
• InChIKey: MJIHNNLFOKEZEW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• IUPAC传统名: 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole; lansoprazole
• 商标名: Agopton; Amarin; Aprazol; Bamalite; Biuret; Biuret Gr; Biuret Reagent; Biuret Reagent Solution; Blason; Compraz; Dakar; Ilsatec; Ketian; Lancid; Lanproton; Lansopep; Lansoprazol [INN-Spanish]; Lansoprazole [Usan:Ban:Inn]; Lansoprazolum [INN-Latin]; Lanston; Lanz; Lanzol-30; Lanzopral; Lanzor; Lasoprol; Limpidex; Mesactol; Monolitum; Ogast; Ogastro; Opiren; Prevacid; Prevacid Iv; Prevacid Solutab; Prevpac; Prezal; Pro Ulco; Promp; Prosogan; Suprecid; Takepron; Ulpax; Zoprol; Zoton
• 别名: lansoprazole; AG 1749; Lansoprazole; 2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole; A-65006; AG-1749; Agopton; Lansox; Lanzor; Limpidex; Ogast; 2-[(R)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole; Dexlansoprazole; R-(+)-Lansoprazole; T 168390; TAK 390; (R)-Lansoprazole; Bamalite; Lanzo; Prezal; Takepron; Zoton; 2-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methylsulfinyl)-1h-benzoimidazole; Prevacid; Prevacid NapraPAC; Prevacid SoluTab; Lansoprazole; 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole

登记号

• CAS号: 103577-45-3; 138530-94-6
• MDL号: MFCD00866873
• PubChem SID: 24278520; 160963794; 46508975
• PubChem CID: 3883

理论计算性质

JChem

• Acid pKa: 9.34671
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 3.013967
• LogD (pH = 7.4): 3.0283315
• Log P: 3.0328553
• 摩尔折射率: 87.608 cm^3
• 极化性: 34.145214 Å^3
• 极化表面积: 67.87 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.84
• LOG S: -3.17
• 溶解度: 2.50e-01 g/l

分子性质

理化性质

• 溶解度: 0.97 mg/L; Chloroform; Methanol
• 外观: Brown Solid; off-white powder; White Solid
• 熔点: 178-182°C dec.; 66-68°C
• 疏水性(logP): 1.9

安全信息

• 保存条件: -20°C; -20°C Freezer; Hygroscopic, Refrigerator, Under inert atmosphere
• 保存注意事项: Hygroscopic
• RTECS编号: DD9487500
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 作用靶点: Proton pump
• 生物活性机理: H-K ATPASE inhibitor; Proton pump inhibitor

产品相关信息

• 纯度: ≥98% (TLC); 97%
• 成盐信息: Free Base
• 应用领域: Used as an antiulcerogenic agent for duodenal ulcers and gastroesophageal reflux disease

详细说明

DrugBank - DB00448

• Drug Groups: approved; investigational
• Description: Lansoprazole is a proton pump inhibitor which prevents the stomach from producing acid. It is manufactured by TAP Pharmaceutical Products. Lansoprazole has been marketed for many years and is one of several PPI's available.
• Indication: For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
• Pharmacology: Lansoprazole, an acid proton-pump inhibitor similar to omeprazole, is used as an untiulcer drug in the treatment and maintenance of healing of duodenal or gastric ulcers, erosive and reflux esophagitis, NSAID-induced ulcer, Zollinger-Ellison syndrome, and Barrett's esophagus. Lansoprozole is active against Helicobacter pylori. The plasma elimination half-life of lansoprazole does not reflect its duration of suppression of gastric acid secretion. Thus, the plasma elimination half-life is less than two hours, while the acid inhibitory effect lasts more than 24 hours.
• Toxicity: Symptoms of overdose include abdominal pain, nausea and diarrhea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Two metabolites have been identified in measurable quantities in plasma (the hydroxylated sulfinyl and sulfone derivatives of lansoprazole). These metabolites have very little or no antisecretory activity. Lansoprazole is thought to be transformed into two active species which inhibit acid secretion by (H^+,K^+)-ATPase within the parietal cell canaliculus, but are not present in the systemic circulation.
• Absorption: The absorption of lansoprazole is rapid, with mean C_max occurring approximately 1.7 hours after oral dosing, and relatively complete with absolute bioavailability over 80%.
• Half Life: 1.5 (± 1.0) hours
• Protein Binding: 97%
• Elimination: Following single-dose oral administration of PREVACID, virtually no unchanged lansoprazole was excreted in the urine. In one study, after a single oral dose of 14C-lansoprazole, approximately one-third of the administered radiation was excreted in the urine and two-thirds was recovered in the feces. This implies a significant biliary excretion of the lansoprazole metabolites.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1354

Research Area: Liver cancer
Biological Activity:
Lansoprazole is a proton-pump inhibitor (PPI) which prevents the stomach from producing gastric acid.It is used to treat duodenal and gastric ulcers, erosive esophagitis, and gastroesophageal reflux disease (GERD). Lansoprazole is also used to treat Zollinger-Ellison syndrome (ZES), which is a condition where the stomach produces too much acid. [1]

Sigma Aldrich - L8533

Biochem/physiol Actions
Gastric proton pump inhibitor.

Toronto Research Chemicals - L175000

Used as a gastric proton pump inhibitor. An antiulcerative.

Toronto Research Chemicals - L175010

The R-enantiomer of Lansoprazole; a gastric proton pump inhibitor. An antiulcerative.

参考文献

• http://www.rxlist.com/prevacid-drug.htm
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• Katsuki, H., et al.: Eur. J. Clin. Pharmacol., 57, 709 (2000)
• Barradell, L.B., et al.: Drugs, 44, 225 (2000)
• Kim, K., et al.: Clin. Pharmacol. Ther., 72, 90 (2000)
• Niioka, T., et al.: Ther. Drug Monit., 28, 3
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