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オメプラゾール 化学構造式
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;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)-6-メトキシ-1H-ベンゾイミダゾール;オメプラゾン;オメプロトン;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)-5-メトキシ-1H-ベンゾイミダゾール;オメプラール;5-メトキシ-2-[[(3,5-ジメチル-4-メトキシピリジン-2-イル)メチル]スルフィニル]-1H-ベンゾイミダゾール;オメプラゾ-ル;オメプラゾール標準品;オメプラゾール (JP17)
MOL File:

オメプラゾール 物理性質

融点 :
沸点 :
600.0±60.0 °C(Predicted)
比重(密度) :
1.332 g/cm3
闪点 :
貯蔵温度 :
H2O: 0.5 mg/mL
pKa 4.14/8.9(H2O,t =25,I=0.025) (Uncertain)
外見 :
水溶解度 :
Soluble in water (0.5 mg/ml), DMSO (25 mg/ml), and ethanol (4.5 mg/ml).
Merck :
Stable, but hygroscopic and photosensitive. Incompatible with strong oxidizing agents. Store in the dark.
CAS データベース:
73590-58-6(CAS DataBase Reference)
1H-Benzimidazole, 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- (73590-58-6)
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xi,T,F
Rフレーズ  36/37/38-39/23/24/25-23/24/25-11
Sフレーズ  26-36-37/39-45-36/37-16-7
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  2
RTECS 番号 DD9087000
HSコード  29333990
有毒物質データの 73590-58-6(Hazardous Substances Data)
毒性 LD50 in mice, rats (g/kg): 0.08, >0.05 i.v.; >4, >4 orally (Ekman)
注意喚起語 Danger
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H303 飲み込むと有害のおそれ 急性毒性、経口 5 P312
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H335 呼吸器への刺激のおそれ 特定標的臓器毒性、単回暴露; 気道刺激性 3 警告
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P304+P340 吸入した場合:空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P311 医師に連絡すること。
P405 施錠して保管すること。

オメプラゾール 価格 もっと(28)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-9785 オメプラゾール
73590-58-6 25g ¥21800 2020-09-21 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-9785 オメプラゾール
73590-58-6 5g ¥82600 2020-09-21 購入
東京化成工業 O0359 オメプラゾール >98.0%(HPLC)(T)
Omeprazole >98.0%(HPLC)(T)
73590-58-6 25g ¥30600 2020-09-21 購入
東京化成工業 O0359 オメプラゾール >98.0%(HPLC)(T)
Omeprazole >98.0%(HPLC)(T)
73590-58-6 5g ¥8600 2020-09-21 購入
Sigma-Aldrich Japan 19329 オメプラゾール analytical standard
Omeprazole analytical standard
73590-58-6 50mg ¥10300 2018-12-25 購入

オメプラゾール 化学特性,用途語,生産方法


白色~うすい黄褐色, 結晶性粉末~粉末




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。


胃酸分泌抑制薬, 消化性潰瘍薬, プロトンポンプ阻害薬


オメプラゾン (田辺三菱製薬); オメプラール (アストラゼネカ)




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.


White Crystalline Solid


Astra (Sweden)


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


diuretic, sweetener, diagnostic aid


A selective proton pump and CYP inhibitor


Omeprazole Pellets are used in the treatment of Gastroesophageal reflux disease (GERD): A condition in which backward flow of acid from the stomach causes heartburn and injury of the food pipe (esophagus)


ChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.

Manufacturing Process

3,5-Lutidine-N-Oxide Hydrogen peroxide (45%, 200 ml) was added dropwise at 60°-70°C during 2 hours to a mixture of 3,5-Lutidine (125 g, 1.16 mole) and acetic acid (400 ml). The mixture was heated to 90°C and maintained at 90°-100°C for 2 hours after which it was cooled to 60°C. Again hydrogen peroxide (45%, 200 ml) was added dropwise at 60°-70°C during 1 hour and then the mixture was heated to 90°C and maintained at 90°-100°C for 6 hours. Thereafter, acetic acid and water was distilled off under reduced pressure and the distillation residue obtained was used as a starting product for the nitration.
3,5-Dimethyl-4-nitropyridine-N-oxide To the distillation above obtained residue was added sulphuric acid (146 ml). Thereafter, a nitrating mixture consisting of sulphuric acid (250 ml) and nitric acid (280 ml) was added dropwise during 4 hours at 90°-100°C. The reactionmixture was heated further at 90°-100°C for 6 hours, after which it was cooled and poured over crushed ice (4 kg), Caustic lye (50%, 1150 ml) was added to the yellow solution and the precipitated crystalline compound was filtered under suction. The cake was washed with water and dried in vacuuo oven to yield the product which melted at 171°-173°C. Yield 78.5%. A sample crystallized from acetone had a melting point of 174°-174.5°C.
3,5-Dimethyl-4-nitropyridine-N-oxide-dimethyl sulfate adduct To a suspension of 3,5-dimethyl-4-nitropyridine-N-oxide (150 g, 0.80 mole) in acetone (450 ml) was added dimethyl sulfate (90 ml, 0.95 mole). The mixture was heated to reflux until a clear solution was obtained and then allowed to cool to ambient temperature. An off-white crystalline solid separated out, which was filtered, washed with acetone and dried to yield 220 g of the adduct. Yield was 83.8% of theoretical.
3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine 3,5-Dimethyl-4-nitropyridine-N-oxide-dimethyl sulfate adduct (220 g, 0.75 mole) was dissolved in methanol (1.0 ltr) and the solution heated to reflux. A solution of ammonium persulfate (140 gm) in water (200 ml) was added dropwise over 4 hours after which reflux was continued for 4 hours. Methanol was distilled off under reduced pressure and the residue was basified to pH 10 by addition of caustic lye (105 ml). The mixture was extracted with dichloromethane (2 times 400 ml). The dichloromethane layer was dried over sodium sulfate and filtered. The product was used as its solution in dichloromethane for the next reaction.
2-Chloromethyl-3,5-dimethyl-4-nitropyridine hydrochloride To the cooled dichloromethane solution of 3,5-dimethyl-2-hydroxymethyl-4nitropyridine was added thionyl chloride (60 ml, 0.85 mole) dropwise over a period of 2 hours and stirring was continued for a further 2 hours. Methanol (10 ml) was added to destroy excess thionyl chloride and separated product was filtered under suction and washed with dichloromethane. The cake was dried in vacuum oven to yield 55 g of a cream colored product. Melting point was 124°-126°C.
5-Methoxy-2-[(3,5-dimethyl-4-nitro-2-pyridinyl)methylthio]-1H-benzimidazole To a suspension of 5-methyl-2-mercaptobenzimidazole (36 g, 0.2 mole), 2chloromethyl-3,5-dimethyl-4-nitropyridine hydrochloride (47.4 g, 0.2 mole) and triethyl benzylammonium chloride (5 g) in a dichloromethane (500 ml) was added dropwise a solution of NaOH (17.6 gm, 0.44 mole) in water (30 ml). The addition was exothermic and the temperature was observed to rise to 40°C with reflux of dichloromethane - the reaction mixture was stirred for further 6 hours at ambient temperature and filtered. The cake was washed with water and dried in vacuum oven to yield 55.8 g of cream color product. Yield 81.1%; melting point 124°-128°C.
5-Methoxy-2-[(3,5-dimethyl-4-nitro-2-pyridinyl)methylthio]-1Hbenzimidazole(50 g, 0.145 mole) was dissolved in methanol and heated to 45°C. A solution of sodium methoxide (50 g, 0.925 mole) in methanol (150 ml) was added dropwise over a period of 3 hours at 45°-60°C. Stirring was continued for another 2 hours and then methanol was distilled off under reduced pressure. To the cooled residue was added water (200 ml) followed by concentrated HCl (65 ml) until the pH of the mixture was 7.5. The reaction mixture was extracted with dichloromethane and the dichloromethane layer was washed with water (2 times 100 ml). The dichloromethane layer was dried over sodium sulfate and concentrated to yield the product as an amber color syrup. Yield was 40.1 gm, about 83.8% of theoretical. A solid sample was obtained by trituration of the syrup several times with petroleum ether. Melting point was 87°-90°C.
5-Methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridinyl)methylthio]-1Hbenzimidazolehydrochloride HCl gas was bubbled into a cooled solution of 5-methoxy-2-[(3,5-dimethyl-4methoxy-2-pyridinyl)methylthiol]-1H-benzimidazole (50 g) in dichloromethane (250 ml) until no more precipitation was observed. The reaction mixture was warmed to 40°C and again cooled to 10°C. The solid was filtered under suction and washed with dichloromethane to yield the product (49 g) as a cream colored fine granular solid. Yield was 88.2% of theoretical. Melting point 144°-148°C.
Omeprazole from 5-methoxy-2-[(3,5-dimethyl-4-methoxy-2pyridinyl)methylthiol]-1H-benzimidazole To a solution of 5-methoxy-2-[(3,5-dimethyl-4-methoxy-2pyridinyl)methylthio]-1H-benzimidazole (32.9 g, 0.1 mole) in dichloromethane (200 ml) was added phthalic anhydride (20 g, 0.135 mole) and cooled in an ice salt bath. This was followed by addition of sodium carbonate (18 g, 0.17 mole) and water (20 ml). Hydrogen peroxide (12 ml, 45%, 0.16 mm mole) was added dropwise at -5°-0°C and the reaction mixture was stirred at the same temperature. When the reaction was complete as indicated by TLC, water (200 ml) was added, cooling bath was removed and the reaction mixture was stirred for 10 mins. The organic layer was separated and washed with 5% sodium carbonate solution. The separated dichloromethane solution was charcoalised and filtered through celite. The filtrate was concentrated to 100 ml and ethyl acetate 100 ml was added thereto. The separated solid was filtered, washed with ethyl acetate and dried in vacuum oven to yield 28.20 g of omeprazole. Yield 82.4% of theoretical. Melting point was 158°-160°C (dec.).

brand name

. Prilosec (AstraZeneca).

Therapeutic Function



Omeprazole was introduced in the 1980s. It belongs to a group of agents that have an inhibitory effect on the secretion of hydrochloric acid in the stomach (gastric acid proton pump inhibitors) and is used in the treatment of upper gastrointestinal tract disorders. The Committee for Proprietary Medicinal Products of the European Commission has concluded that a causal association between the reactions reported in Germany and the use of omeprazole had not been established. Nevertheless oral administration should be preferred. (Reference: (CPMPPO) Pharmacovigilance Opinion, No.16 , , 25 July 1994)


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.


H + ,K + -ATPase inhibitor (IC 50 = 5.8 μ M) that displays antisecretory and antiulcer activity. Inhibits gastric acid secretion (IC 50 = 0.16 μ M for histamine-induced acid formation) and reduces gastric lesion formation induced by a variety of ulcerative stimuli. Antibacteral against Helicobacter pylori in vitro . Also inhibits CYP2C19, CYP2C9 and CYP3A (K i values are 3.1, 40.1 and 84.4 μ M respectively) and blocks swelling-dependent chloride channels (ICIswell).

Veterinary Drugs and Treatments

Omeprazole is potentially useful in treating both gastroduodenal ulcer disease and to prevent or treat gastric erosions caused by ulcerogenic drugs (e.g., aspirin). An oral paste product is labeled for the treatment and prevention of recurrence of gastric ulcers in horses.


When male humans are given 14C-omeprazole orally, an average of 79% of the dose is recovered in the urine in 96 h. Omeprazole is completely metabolized and at least six metabolites are identified. Two major metabolites are hydroxyomeprazole and omeprazole acid.

オメプラゾール 上流と下流の製品情報



オメプラゾール 生産企業

Global( 487)Suppliers
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Jiangsu Zhongbang Pharmaceutical Co., Ltd.
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86-0551-65418684 18949823763
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QQ:800182836 CHINA 2886 58
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Accela ChemBio Inc.
(+1)-858-876-1948 United States 19969 58


  • 73590-58-6
  • 1h-benzimidazole,5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulf
  • 2-Chloromethyl-3,5-dinmethyl-4-methoxypyridine
  • 5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl)benzimidazol
  • audazol
  • aulcer
  • belmazol
  • ceprandal
  • elgam
  • emeproton
  • gastrimut
  • indurgan
  • miol
  • omapren
  • ompanyt
  • parizac
  • pepticum
  • prysma
  • sanamidol
  • secrepina
  • ulceral
  • ulcometion
  • ulcsep
  • zimor
  • H 168/68
  • 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
  • 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)-6-メトキシ-1H-ベンゾイミダゾール
  • オメプラゾン
  • オメプロトン
  • 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)-5-メトキシ-1H-ベンゾイミダゾール
  • オメプラール
  • 5-メトキシ-2-[[(3,5-ジメチル-4-メトキシピリジン-2-イル)メチル]スルフィニル]-1H-ベンゾイミダゾール
  • オメプラゾ-ル
  • オメプラゾール標準品
  • オメプラゾール (JP17)
  • 胃液分泌抑制薬
  • 消化性潰瘍薬
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