Pantoprazole

Base Information

• Chemical Name: Pantoprazole
• CAS No.: 102625-70-7
• Molecular Formula: C16H15F2N3O4S
• Molecular Weight: 383.376
• European Community (EC) Number: 600-331-6
• NSC Number: 759257
• UNII: D8TST4O562
• DSSTox Substance ID: DTXSID4023416
• Nikkaji Number: J324.079G
• Wikipedia: Pantoprazole
• Wikidata: Q286846
• NCI Thesaurus Code: C29346
• RXCUI: 40790
• Pharos Ligand ID: DFAW56J9FNCT
• Metabolomics Workbench ID: 38704
• ChEMBL ID: CHEMBL1502
• Mol file: 102625-70-7.mol

Synonyms:BY 1023;BY-1023;BY1023;pantoprazole;pantoprazole sodium;Protonix;SK and F 96022;SK and F-96022;SK and F96022;SKF 96022;SKF-96022;SKF96022

Chemical Property of Pantoprazole

Chemical Property:

• Appearance/Colour: almost white solid
• Vapor Pressure: 9.37E-14mmHg at 25°C
• Melting Point: 139-140oC, decomposes
• Refractive Index: 1.642
• Boiling Point: 586.9 °C at 760 mmHg
• PKA: pKa1 3.92; pKa2 8.19(at 25℃)
• Flash Point: 308.7 °C
• PSA: 105.54000
• Density: 1.51 g/cm³
• LogP: 3.75000
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 383.07513347
• Heavy Atom Count: 26
• Complexity: 490

Purity/Quality:

99% ^*data from raw suppliers

Pantoprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-37/38-41-48
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiulcer Agents
• Canonical SMILES: COC1=C(C(=NC=C1)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC(F)F)OC
• Recent ClinicalTrials: Neuro-immune Interactions and PPI
• Recent EU Clinical Trials: AN EXPLORATORY, MULTICENTER, RANDOMIZED, DOUBLE BLIND STUDY OF CLINICAL OUTCOMES, TOLERABILITY, AND SAFETY OF 2 DOSES OF ORAL PANTOPRAZOLE IN PEDIATRIC PARTICIPANTS AGED 1 TO 11 YEARS AND 12 TO 17 YEARS WHO REQUIRE MAINTENANCE THERAPY FOR HEALED EROSIVE ESOPHAGITIS
• Description: Pantoprazole, an irreversible proton pump inhibitor, reached its first market worldwide in Germany for acute treatment of gastric and duodenal ulcers and gastroesophageal reflux disease. Proton pump inhibitors are more effective than other strategies in inhibiting acid secretion since they function at the final step of acid production, therefore, provide superior symptom relief and healing in all acid related diseases. As the third substituted benzimidazole proton pump inhibitor marketed, pantoprazole not only has superior ulcer-preventing effect but also is more potent than omeprazole in healing acetic acid-induced gastric and duodenal ulcers with extremely low acute toxicity. The mechanism of action for this class of compounds has been suggested to be mediated via the protonated form of the molecule which selectively reacts with cysteines present on the extracytoplasmic face of the enzyme to form covalent disulfide bonds.
• Uses: proton pump inhibitor, gastric acid release inhibitor, antiulcer
• Therapeutic Function: Antiulcer
• Clinical Use: Pantoprazole
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: effect of coumarins possibly enhanced. Antifungals: absorption of itraconazole and ketoconazole reduced; avoid with posaconazole. Antivirals: concentration of atazanavir and rilpivirine reduced - avoid; concentration of raltegravir and saquinavir possibly increased - avoid. Clopidogrel: possibly reduced antiplatelet effect. Cytotoxics: possibly reduced excretion of methotrexate; avoid with dasatinib, erlotinib and vandetanib; possibly reduced lapatinib absorption; possibly reduced absorption of pazopanib. Ulipristal: reduced contraceptive effect, avoid with high dose ulipristal.

Technology Process of Pantoprazole

There total 22 articles about Pantoprazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

pantoprazole sulfide (102625-64-9) → 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (102625-70-7)

Guidance literature:

With sodium hydroxide; N-chlorophthalimide; In DMF (N,N-dimethyl-formamide); water; acetonitrile; at -10 - 20 ℃; for 1.75h;

Reference yield: 78.0%

5-(difluoromethoxy)-2-[[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (409098-86-8) + sodium methylate (124-41-4) → 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (102625-70-7)

Guidance literature:

In methanol; for 50h; Product distribution / selectivity; Heating / reflux;

Reference yield: 71.0%

pantoprazole sulfide (102625-64-9) → 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (102625-70-7) + Pantoprazole sulfone

Guidance literature:

With sodium hydroxide; sodium hypochlorite; In water; ethyl acetate; at -10 - 20 ℃; for 1.83333 - 3.25h;

upstream raw materials:

pantoprazole sulfide

5-(difluoromethoxy)-2-[[(3,4-dimethoxypyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole

3-methoxy-2-methyl-4-nitropyridine 1-oxide

3-methoxy-2-methylpyridin-4(1H)-one

Downstream raw materials:

pantoprazole sodium

2-{4-[(6-(difluoromethoxy)-2-{[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl}benzimidazol-1-yl)sulfonyl]phenoxy}-N-(2-pyridyl)acetamide

2-{4-[(5-(difluoromethoxy)-2-{[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl}benzimidazol-1-yl)sulfonyl]phenoxy}-N-(2-pyridyl)acetamide

5‐(difluoromethoxy)‐2‐[(3,4‐dimethoxy‐2‐pyridyl)methylsulfinyl]‐1H‐benzimidazole

Refernces

• 1、 -. "Method for preparing benzimidazole proton pump inhibitor". Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024-0041. . Retrieved 2018/09/08.
• 2、 -. "Method for preparing high-purity razole intermediate and medicine by using green technology instead of phosgene, thionyl chloride and other toxic and harmful substances". Paragraph 0101; 0102. . Retrieved 2017/09/01.