6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

• ChemBase编号: 222
• 分子式: C17H19N3O3S
• 平均质量: 345.41606
• 单一同位素质量: 345.11471248
• SMILES: S(=O)(Cc1ncc(c(OC)c1C)C)c1[nH]c2c(n1)ccc(OC)c2
• Canonical SMILES: COc1ccc2c(c1)[nH]c(n2)S(=O)Cc1ncc(c(c1C)OC)C
• InChI: InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
• InChIKey: SUBDBMMJDZJVOS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole; 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
• IUPAC传统名: 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-3H-1,3-benzodiazole; 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole; antra; omeprazole
• 商标名: Nexiam; Nexium; Nexium IV; Lucen; Esopral; Axagon; Antra; Audazol; Aulcer; Belmazol; Ceprandal; Danlox; Demeprazol; Desec; Dizprazol; Dudencer; Elgam; Emeproton; Epirazole; Erbolin; Exter; Gasec; Gastrimut; Gastroloc; Gibancer; Indurgan; Inhibitron; Inhipump; Lensor; Logastric; Lomac; Losec; Mepral; Miol; Miracid; Mopral; Morecon; Nilsec; Nopramin; Ocid; Olexin; Omapren; Omebeta 20; Omed; Omegast; Omepral; Omeprazon; Omeprol; Omesek; Omezol; Omezolan; Omid; Omisec; Omizac; Ompanyt; Ortanol; Osiren; Ozoken; Paprazol; Parizac; Pepticum; Pepticus; Peptilcer; Prazentol; Prazidec; Prazolit; Prilosec; Procelac; Proclor; Prysma; Ramezol; Regulacid; Result; Sanamidol; Secrepina; Tedec Ulceral; Ulceral; Ulcesep; Ulcometion; Ulcozol; Ulcsep; Ulsen; Ultop; Ulzol; Victrix; Zefxon; Zegerid; Zepral; Zimor; Zoltum
• 别名: Esomeprazole Sodium; Esomperazole; esomeprazole; Esomeprazole; 6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole; (±)-Omeprazole; Gastrogard; Gastroloc; Mepral; Mopral; Omepral; Zoltum; Audazol; Belmazol; Logastric; Omapren; Omeprazen; Parizac; 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole; Omeprazol [INN-Spanish]; Omeprazolum [INN-Latin]; OMEP; OMZ; OMP; Omeprazole magnesium; omeprazole; Omeprazole; Prilosec; Zegerid; Prilosec OTC; 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole; Antra; Losec; Omeprazole; 5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole; 5-methoxy-2-((4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl)-3h-benzoimidazole

登记号

• CAS号: 161796-78-7; 73590-58-6; 131959-78-9
• MDL号: MFCD00002233; MFCD00083192
• PubChem SID: 160963685; 46509065; 24897870
• PubChem CID: 4594

理论计算性质

JChem

• Acid pKa: 9.294158
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 2.361715
• LogD (pH = 7.4): 2.4276938
• Log P: 2.433509
• 摩尔折射率: 93.6623 cm^3
• 极化性: 37.349922 Å^3
• 极化表面积: 77.1 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.66
• LOG S: -2.98
• 溶解度: 3.59e-01 g/l

分子性质

理化性质

• 溶解度: 82.3 mg/L; Acetonitrile; DMSO; DMSO: >19 mg/mL; Ethanol; ethanol: soluble4.5 mg/mL; H2O: soluble0.5 mg/mL; Very slightly soluble in water
• 外观: white solid; White to Off-White Solid
• 熔点: 148-150°C (dec.)
• 疏水性(logP): 0.6; 2.565

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: DD9087000
• 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: adrenergic receptor
• 相关基因信息: human ... ABCB1(5243), CYP1A2(1544)
• 生物活性机理: Inhibits gastric acid secretion; Proton pump inhibitor

产品相关信息

• 纯度: 95%; 98%
• 成盐信息: Free Base
• 应用领域: Antiulcer agent
• Pharmacopeia Traceability: traceable to BP 765; traceable to PhEur O0150000; traceable to USP 1478505
• Empirical Formula (Hill Notation): C17H19N3O3S

详细说明

DrugBank - DB00338

• Drug Groups: approved; investigational
• Description: A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and zollinger-ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of gastric parietal cells. [PubChem]
• Indication: For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
• Pharmacology: Omeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Omeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H^+/K^+ ATPase at the secretory surface of the gastric parietal cell. As a result, it inhibits acid secretion into the gastric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
• Toxicity: Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Absorption is rapid, absolute bioavailability (compared to intravenous administration) is about 30-40% at doses of 20-40 mg.
• Half Life: 0.5-1 hour
• Protein Binding: 95%
• Elimination: Urinary excretion is a primary route of excretion of omeprazole metabolites.
• Clearance: * total body cl=500-600 mL/min [healthy]; * 250 mL/min [Geriatric]; * 70 mL/min [Hepatic Impairment]; * 10 - 62 mL/min/1.73 m2 [Renal Impairment]
• References: Yang YX, Lewis JD, Epstein S, Metz DC: Long-term proton pump inhibitor therapy and risk of hip fracture. JAMA. 2006 Dec 27;296(24):2947-53. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

DrugBank - DB00736

• Drug Groups: approved; investigational
• Description: A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and zollinger-ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of gastric parietal cells. [PubChem]
• Indication: For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
• Pharmacology: Esomeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Esomeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H^+/K^+ ATPase at the secretory surface of the gastric parietal cell. By doing so, it inhibits acid secretion into the gsatric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
• Toxicity: Blurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating
• Affected Organisms: Humans and other mammals
• Biotransformation: Mainly hepatic. Esomeprazole is completely metabolized by the cytochrome P450 system via CYP2C19 and CYP3A4. Metabolism produces inactive hydroxy and desmethyl metabolites, which have no effect on gastric acid secretion. Less than 1% of the parent drug is excreted in urine.
• Absorption: 90%
• Half Life: 1-1.5 hours
• Protein Binding: 97%
• Elimination: Approximately 80% of the administered dose of esomeprazole is excreted as metabolites in urine and the remaining 20% is excreted in feces.
• Distribution: * 16 L [healthy volunteers]
• References: Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1389

Research Area: Gastro-oesophageal reflux
Biological Activity:
Omeprazole(Prilosec) is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD), laryngopharyngeal reflux (LPR), and Zollinger-Ellison syndrome. [1]

Sigma Aldrich - O104

Biochem/physiol Actions
Binds covalently to proton pump; inhibits gastric secretion.
Caution
Hygroscopic, photosensitive

Toronto Research Chemicals - O635000

Binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative.

参考文献

• Yang YX, Lewis JD, Epstein S, Metz DC: Long-term proton pump inhibitor therapy and risk of hip fracture. JAMA. 2006 Dec 27;296(24):2947-53. Pubmed
• Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. Pubmed
• http://en.wikipedia.org/wiki/Omeprazole
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