Rabeprazole Sodium

Base Information

• Chemical Name: Rabeprazole Sodium
• CAS No.: 117976-90-6
• Deprecated CAS: 226904-80-9,129982-41-8,1017795-22-0
• Molecular Formula: C18H20N3NaO3S
• Molecular Weight: 381.431
• Hs Code.: 2933399090
• European Community (EC) Number: 629-730-3
• UNII: 3L36P16U4R
• ChEMBL ID: CHEMBL1200930
• DSSTox Substance ID: DTXSID3044205
• NCI Thesaurus Code: C80692
• Nikkaji Number: J561.822C
• RXCUI: 226868
• Wikidata: Q27108142
• Mol file: 117976-90-6.mol

Synonyms:1H-Benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, sodium salt;2-((4-(3-methoxypropoxy)-3-methylpyridin-2-yl)methylsulfinyl)-1H-benzimidazole;Aciphex;dexrabeprazole;E 3810;E3810;LY 307640;LY-307640;LY307640;Pariet;rabeprazole;rabeprazole sodium;Sodium, Rabeprazole

Chemical Property of Rabeprazole Sodium

Chemical Property:

• Appearance/Colour: white or off white crystalline powder
• Melting Point: 140-141 °C
• Boiling Point: 603.9 °C at 760 mmHg
• Flash Point: 319.1 °C
• PSA: 93.41000
• Density: 0.45~0.55 g/mL
• LogP: 3.48420
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: H2O: soluble10mg/mL (clear solution)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 381.11230696
• Heavy Atom Count: 26
• Complexity: 446

Purity/Quality:

99%, ^*data from raw suppliers

Rabeprazole Sodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3[N-]2)OCCCOC.[Na+]
• Recent ClinicalTrials: A Study to Compare the Safety, Pharmacokinetics and Pharmacodynamics of YPI 011 to Rabeprazole in Healthy Adult Subjects
• Recent EU Clinical Trials: ASSOCIATION BETWEEN PROTON-PUMP INHIBITORS (PPI) and METRONOMIC CAPECITABINE (mCAP) AS SALVAGE TREATMENT FOR PATIENTS WITH ADVANCED GASTRO-INTESTINAL TUMOURS: A RANDOMIZED PHASE II STUDY
• Recent NIPH Clinical Trials: The efficacy and safety of rabeprazole sodium 20mg against reflux esophagitis associated with systemic scleroderma
• Uses: It belongs to national second-class drug that can be used for the treatment of gastric ulcer. It can be used for the treatment of peptic ulcer, gastroesophageal reflux disease, zollinger-ellison syndrome and other diseases. Rebeprazole sodium is a partially reversible gastric proton pump inhibitor anthelminthic, antiseptic, expectorant antibacterial and antifungal agent effective against gram-positive and gram-negative bacteria, yeast and fungi
• Description: Rebeprazole sodium was launched as Pariet in Japan, its first market, for the treatment of peptic ulcers including gastric and duodenal ulcers. From 4-chloro- 2,3-dimethylpyridine N-oxide, a six step synthesis allows access to the basic skeleton after successive condensations. Rabeprazole, a structural analog of Omeprazole, the first compound to have been marketed in this class up to now, is reported to be a more potent inhibitor of gastric H+/K+-adenosine triphosphate (ATPase) ; a common mechanism of action of this chemical class involves the conversion at low pH to a reactive sulphonamide that itself binds to cysteine residues located on the enzyme. Moreover, rabeprazole showed an antibacterial activity against Helicobacter Pylori, with a MIC90 of 1.56 μg/ml. Rebeprazole sodium has a faster onset of action compared with omeprazole, but a shorter duration of action, being extensively and rapidly metabolized in several animal species. In clinical studies in patients with gastric ulcers, 10 and 20 mg rabeprazole sodium once-daily significantly inhibited basal and stimulated acid output. Rabeprazole is awaiting registration in the US for treatment of gastrooesophageal reflux disease (GORD) and other pathologic hypersecretory conditions including Zollinger-Ellison syndrome. Rabeprazole is a proton pump inhibitor that selectively and irreversibly inhibits the gastric H+/K+ ATPase (IC50 = 72 nM). It can be activated more rapidly and over a greater pH range than other proton pump inhibitors such as omeprazole , lansoprazole , and pantoprazole . Rabeprazole (30 mg/kg) inhibits gastric acid secretion in pylorus-ligated rats and a rat model of gastric fistula. It also inhibits the growth of several strains of H. pylori in vitro (MIC50s = 1.57-3.13 μg/mL). Formulations containing rabeprazole have been used in the treatment of ulcers, pathological hypersecretory conditions, and gastroesophageal reflux disease (GERD).
• Clinical Use: Gastric acid suppression
• Drug interactions: Potentially hazardous interactions with other drugs 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 Rabeprazole Sodium

There total 18 articles about Rabeprazole Sodium 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: 100.0%

rabeprazole (117976-89-3,177795-59-4) → Rabeprazole sodium (117976-90-6)

Guidance literature:

With sodium hydroxide; In ethanol; Product distribution / selectivity;

Reference yield: 100.0%

2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylsulfinyl]-1H-benzimidazole, cyclopentylamine salt → Rabeprazole sodium (117976-90-6)

Guidance literature:

With sodium hydroxide; In water; Product distribution / selectivity;

Reference yield: 99.3%

2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methysulfinyl]-1H-benzimidazole, sec-butylamine salt → Rabeprazole sodium (117976-90-6)

Guidance literature:

With sodium hydroxide; In water; Product distribution / selectivity;

upstream raw materials:

rabeprazole

rabeprazole sulfide

LY 307640 sulfone

Benzimidazol-2-thiol

Downstream raw materials:

1-(2,5-dichlorophenylsulfonyl)-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole

1-phenacyl-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole

1-(4-nitrobenzyl)-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole

1-cinnamyl-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole

Refernces

• 1、 -. "Preparation method for key intermediate rabeprazole thioether". Paragraph 0026-0027. . Retrieved 2017/07/12.
• 2、 -. "A process for the preparation of sodium rebeilazole for". Paragraph 0021; 0022. . Retrieved 2016/10/07.