Pantoprazole Sodium CAS 138786-67-1
Introduction：Basic information about Pantoprazole Sodium CAS 138786-67-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Pantoprazole Sodium Basic information
| Product Name: | Pantoprazole Sodium |
| Synonyms: | 5-(DIFLUOROMETHOXY)-2-[[(3,4-DIMETHOXY-2-PYRIDINYL)METHYL]SULFINYL]-1H-BENZIMIDAZOLE;5-(difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl) sulfinyl)-1h-benzimidazole sodium;1h-benzimidazole,5-(difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl)sul;5-(difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-1h-benzi;midazolesodium;EUPANTOL;PANTOPRAZOLE SODIUM;PANTOPRAZOLE, SODIUM SALT |
| CAS: | 138786-67-1 |
| MF: | C16H14F2N3NaO4S |
| MW: | 405.35 |
| EINECS: | 604-093-4 |
| Product Categories: | Pantoprazole;Antibiotic Explorer;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Heterocycles;Sulfur & Selenium Compounds;Active Pharmaceutical Ingredients;138786-67-1 |
| Mol File: | 138786-67-1.mol |
Pantoprazole Sodium Chemical Properties
| Melting point | 199-202°C |
| storage temp. | Inert atmosphere,Store in freezer, under -20°C |
| solubility | DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly) |
| form | Solid |
| color | White to Pale Beige |
| Stability: | Hygroscopic |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1S/C16H14F2N3O4S.Na/c1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16;/h3-7,15H,8H2,1-2H3;/q-1;+1 |
| InChIKey | YNWDKZIIWCEDEE-UHFFFAOYSA-N |
| SMILES | C12C=C(C=CC=1N(C(S(=O)CC1N=CC=C(OC)C=1OC)=N2)[Na])OC(F)F |
| CAS DataBase Reference | 138786-67-1(CAS DataBase Reference) |
| CAS Number Unlabeled | 138786-67-1 |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20/21/22-37/38-41-48 |
| Safety Statements | 22-26-36/37/39-45 |
| WGK Germany | nwg |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Chemical Properties | White to Off-White Solid |
| Originator | Controloc,Byk Gulden ,Germany |
| Uses | Gastrointestinal |
| Uses | An antiulcerative. Gastric pump inhibitor. |
| Definition | ChEBI: Pantoprazole sodium is an organic sodium salt. It has a role as an EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor and an anti-ulcer drug. It contains a pantoprazole(1-). |
| Manufacturing Process | 2-Chloromethyl-4,5-dimethoxy-3-methylpyridinium chloride (about 1.5 g) are added to a solution of 5-difluoromethoxy-1H-benzimidazole-2-thiol in 10 ml of ethanol and 10 ml of 1 N sodium hydroxide solution. The yellow reaction mixture is stirred at 20°C for 1 hour, a further 10 ml of water are added,whereupon a colorless solid precipitates out, the mixture is stirred for a further 5 hours and filtered and the residue is rinsed with 1 N sodium hydroxide solution and water and dried to constant weight. The 5difluoromethoxy-2-[(4,5-dimethoxy-2-pyridyl)methylthio]-1H-benzimidazole is obtained as an oil. 5-Difluoromethoxy-2-[(4,5-dimethoxy-2-pyridyl)methylthio]-1H-benzimidazole (about 1 g) are dissolved in 10 ml of dioxane and 2 ml of 1 N sodium hydroxide solution. An equimolar amount of a titrated aqueous sodium hypochlorite solution, to which 1 mole per liter of sodium hydroxide solution has been added, is first added dropwise, while cooling with ice. After one hour a further equivalent and after 3 hours half the equimolar amount of sodium hypochlorite are added, to achieve complete reaction. After a reaction time of 4 hours, 5 ml of 5% strength sodium thiosulfate solution and another 25 ml of dioxane are added and the upper dioxane phase is separated off, washed once with 5 ml of sodium thiosulfate solution and concentrated on a rotary evaporator. The oily residue is dissolved in 20 ml of water and 10 ml of ethyl acetate and the solution is brought to pH 7 with about 100 ml of a buffer solution of pH 6.8. The solid which has precipitated out is filtered off with suction over a suction filter, washed with water, extracted by stirring at 0C with acetone and dried. 5-Difluoromethoxy-2-[(4,5-dimethoxy-2pyridyl)methanesulfinyl]-1H-benzimidazole is prepared; yield about 85%. |
| Brand name | Protonix (Wyeth). |
| Therapeutic Function | Antiulcer |
| General Description | Pantoprazole sodium, racemicsodium5-(difluoromethoxy)-2-[[3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole sesquihydrate is a white tooff-white crystalline powder that is freely soluble in water,very slightly soluble in phosphate buffer at pH 7.4, and practicallyinsoluble in n-hexane. The benzimidazole of this drughas a weakly basic nitrogen (pyridine N, pKa 3.83) and an benzimidazoleproton (pKa 0.11), facilitating formulation as asodium salt. The stability of the compound in aqueous solutionis pH dependent; the rate of degradation increases with decreasingpH. At ambient temperature, the degradation half-lifeis approximately 2.8 hours at pH 5.0 and approximately 220hours at pH 7.8. The absorption of pantoprazole is rapid (Cmax of2.5μg/mL, Tmax 2.5 hours) after single or multiple oral40-mg doses. Pantoprazole is well absorbed (77% bioavailability).Administration with food may delay its absorptionbut does not alter pantoprazole bioavailability. Pantoprazoleis distributed mainly in extracellular fluid. The serum proteinbinding of pantoprazole is about 98%, primarily to albumin.Pantoprazole is extensively metabolized in the liver throughthe CYP system, including O-demethylation (CYP2C19),with subsequent sulfation. Other metabolic pathways includesulfur oxidation by CYP3A4. There is no evidencethat any of the pantoprazole metabolites have significantpharmacological activity. Approximately 71% of a dose of pantoprazole is excreted in the urine, with 18% excretedin the feces through biliary excretion. |
| Biological Activity | Gastric proton pump inhibitor. It is used for short-term treatment of erosion and ulceration of the esophagus caused by gastroesophageal reflux disease. |
| References | [1] Patent: WO2004/111029, 2004, A2. Location in patent: Page 24 [2] Patent: CN107011252, 2017, A. Location in patent: Paragraph 0101; 0103 [3] Patent: WO2004/111029, 2004, A2. Location in patent: Page 24 [4] Patent: WO2009/75516, 2009, A2. Location in patent: Page/Page column 5 [5] Patent: WO2004/111029, 2004, A2. Location in patent: Page 24 |
Pantoprazole Sodium Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Sodium thiosulfate-->5-(Difluoromethoxy)-1H-Benzimidazole-2-thiol-->Sodium hypochlorite-->Pantoprazole-->5-(Difluoromethoxy)-2[[(4-chloro-3-methoxy-2-pyridinyl)methyl]-thio]-1H-benzimidazole-->5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole-->5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole-->2-[(4-chloro-3-methoxypyridin-2-yl)methanesulfinyl]-6-(difluoromethoxy)-1H-1,3-benzodiazole-->2-Chloromethyl-3,4-dimethoxypyridinium chloride |
