オメプラゾール
5-メトキシ-2-[(3,5-ジメチル-4-メトキシ-2-ピリジル)メチルスルフィニル]-1H-ベンゾイミダゾール · 5-メトキシ-2-[[(4-メトキシ-3,5-ジメチル-2-ピリジニル)メチル]スルフィニル]-1H-ベンゾイミダゾール · エンプラール · オメラップ · オメプラゾール · 5-メトキシ-2-[(3,5-ジメチル-4-メトキシ-2-ピリジニル)メチルスルフィニル]-1H-ベンゾイミダゾール · オメプトロール · オブランゼ
識別子と物理属性
| CAS No. | 668985-31-7 |
|---|---|
| 分子式 | C34H38MgN6O7S2 |
| 平均分子量 | 731.14 g/mol |
| SMILES | COc1ccc2nc(S(=O)Cc3ncc(C)c(OC)c3C)[nH]c2c1 |
| InChIKey | SUBDBMMJDZJVOS-UHFFFAOYSA-N |
| PubChem CID | 4594 |
| ChEBI | CHEBI:91766 |
| EC No. | 695-602-9 |
| 現地名 | オメプラゾール |
化学・物理的性質
| XLogP | 2.2 |
|---|---|
| 極性表面積 | 96.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 5 |
| 重原子数 | 24 |
| 形式電荷 | 0 |
| 複雑度 | 453 |
| 融点 | 156°C |
| 沸点 | 600.0±60.0 °C(Predicted) |
| 密度 | 1.332 g/cm3 |
| 引火点 | 9℃ |
| 貯蔵条件 | 2-8°C |
| 溶解度 | H2O: 0.5 mg/mL水 (0.5 mg/ml)、DMSO (25 mg/ml)、エタノール (4.5 mg/ml) に溶解。 |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | pKa 4.14/8.9(H2O,t =25,I=0.025) (Uncertain) |
| 色 | 白い |
| Merck | 14,6845 |
| BCS Class | 2 |
| 安定性 | 安定していますが、吸湿性と感光性があります。強力な酸化剤とは相容れない。光から遠ざけてください。 |
| 主な用途 | 法医学と毒物学医薬品（低分子化合物） |
| 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 |
| SMILES | COc1ccc2[nH]c(nc2c1)S(=O)Cc3ncc(C)c(OC)c3C |
| CAS データベース | 73590-58-6(CAS DataBase Reference) |
| EPAの化学物質情報 | 1H-Benzimidazole, 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- (73590-58-6) |
化学的特性
White Crystalline Solid
安全性と法規制
| 水環境危害等級（WGK） | 2 |
|---|---|
| RTECS 番号 | DD9087000 |
| 輸送番号（UN） | UN1230 - class 3 - PG 2 - Methanol, solution |
| 毒性 | LD50 in mice, rats (g/kg): 0.08, >0.05 i.v.>4, >4 orally (Ekman) |
| 税関コード | 29333990 |
| 危険文句（R） | 36/37/38-39/23/24/25-23/24/25-11 |
| 危険表示 | Xi,T,F |
| 安全措置（S） | 26-36-37/39-45-36/37-16-7 |
| 危険等級 | Acute Tox. 4 OralAquatic Chronic 2Skin Sens. 1 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 73590-58-6(Hazardous Substances Data) |
用途
用途
プロトンポンプ阻害剤です。 胃酸生成細胞である壁細胞に移行し、H+、 K+-ATPase活性を強く抑制して胃酸分泌を抑 制します。
説明
Omeprazole is a potent gastric antisecretory agent with selective inhibitory effect on the H+,K+-ATPase proton pump. It is highly effective in the treatment of duodenal ulcer and Zollinger-Ellison syndrome, and is reportedly superior to ranitidine in the management of reflux esophagitis.
来歴
Omeprazole was first approved by the FDA in 1989 in the form of extended-release capsules for the treatment of acid-related disorders. Brand name Prilosec, it was initially used over-the-counter (OTC) for adults to help control heartburn that occurs two or more days a week.
使用
Omeprazole is a proton pump inhibitor used to treat diseases like gastroesophageal reflux disease (GERD), used for gastric and duodenal ulcers, reflux or erosive esophagitis, and Zollinger-Ellison syndrome. It is also effective for gastric and duodenal ulcers that are ineffective with H2 receptor antagonists. Injections of Omeprazole can also be used for: 1 gastrointestinal bleeding, such as peptic and anastomic ulcer bleeding, and the prevention of severe diseases (such as cerebral hemorrhage, severe trauma, etc.) and gastric surgery caused by upper intestinal bleeding; 2 acute gastric mucosal damage complicated by stress or nonsteroidal anti-inflammatory drugs; 3 general anesthesia, post-surgery, or coma patients, to prevent acid reflux and aspiration pneumonia; 4 Combined with amoxicillin and clarithromycin, or with metronidazole and clarithromycin, it can effectively kill Helicobacter pylori (Hp).
一般的な説明
Omeprazole, 5-methoxy-2-(((4-methoxy-3, 5-dimethyl-2-pyridinyl)methyl) sulfinyl)-1Hbenzimidazole(Losec), is a white to off-white crystallinepowder with very slight solubility in water. Omeprazole isan amphoteric compound (pyridine N, pKa 4.06; benzimidazoleN-H, pKa 0.79), and consistent with the proposedmechanism of action of the substituted benzimidazoles, isacid labile. Hence, the omeprazole product is formulatedas delayed-release capsules containing enteric-coatedgranules.The absolute bioavailability of orally administeredorneprazole is 30% to 40% related to substantial first-passbiotransformation. The drug has a plasmahalf-life of about 1 hour. Most (77%) of an oral dose ofomeprazole is excreted in the urine as metabolites with insignificantantisecretory activity. The primary metabolitesof omeprazole are 5-hydroxyomeprazole (CYP2C19) andomeprazole sulfone (CYP3A4). The antisecretory actions ofomeprazole persist for 24 to 72 hours, long after the drughas disappeared from plasma, which is consistent with itssuggested mechanism of action involving irreversible inhibitionof the proton pump.Omeprazole is approved for the treatment of heartburn,GERD, duodenal ulcer, erosive esophagitis, gastric ulcer,and pathological hypersecretory conditions.
製法・合成法
製造方法
The antiulcer agent omeprazole is produced from 2,3,5-trimethylpyridine N-oxide.Synthesis and Structure of OmeprazoleSteps: 2-(Lithium methyl sulphinyl)-5-methoxy-1H benzimidazole 20g was reacted with 2-chloro-3,5-dimethyl-4-methoxy pyridine 21 g to form sulphide intermediate and then converted to Omeprazole when treated with m-CPBA which used as anoxidizingagents. The acetamide-sulfide compounds modification are oxidised to form the amide sulfinyl compound and gives the sulfinyl carboxylate or salts upon alkaline hydrolysis.On further decarboxylation leads to the target molecules. The residual, unreacted salt, inorganic by-products and other minor by-products can be easily purified by a simple washing from omeprazole or lansoprazole. The amide compounds containing crystalline solids as opposed to the sulphide and sulfoxides of the reported procedures.DOI: http://dx.doi.org/10.20902/IJPTR.2019.120307