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HomeProduct name listRebeprazole sodium

Rebeprazole sodium

Synonym(s):2-([4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole;Pariprazole;Rabeprazole sodium

  • CAS NO.:117976-90-6
  • Empirical Formula: C18H21N3O3S.Na
  • Molecular Weight: 382.43
  • MDL number: MFCD02092688
  • EINECS: 629-730-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 13:32:20
Rebeprazole sodium Structural

What is Rebeprazole sodium?

Description

Rebeprazole sodium, marketed as Pariet in Japan, was initially launched for the treatment of peptic ulcers, including both gastric and duodenal ulcers. It is synthesized through a six-step process starting from 4-chloro-2,3-dimethylpyridine N-oxide, which allows the formation of its basic skeleton through successive condensations.

Description

Rabeprazole is a proton pump inhibitor with the ability to selectively and irreversibly inhibit the gastric H+/K+ ATPase enzyme, showing an IC50 value of 72 nM. It demonstrates a faster activation and a broader pH range of effectiveness compared to other proton pump inhibitors such as omeprazole, lansoprazole, and pantoprazole.

In studies, rabeprazole has been shown to inhibit gastric acid secretion in animal models, specifically in pylorus-ligated rats and a rat model of gastric fistula, when administered at a dosage of 30 mg/kg. Additionally, it has been found to inhibit the growth of several strains of Helicobacter pylori in vitro, with MIC50 values ranging from 1.57 to 3.13 μg/mL.

Formulations containing rabeprazole are utilized in the treatment of various conditions, including ulcers, pathological hypersecretory conditions, and gastroesophageal reflux disease (GERD).

Chemical properties

Rebeprazole sodium is White Crystalline Solid

Originator

Eisai (Japan)

The Uses of Rebeprazole sodium

Rebeprazole sodium is a partially reversible gastric proton pump inhibitor

The Uses of Rebeprazole sodium

anthelminthic, antiseptic, expectorant

The Uses of Rebeprazole sodium

antibacterial and antifungal agent effective against gram-positive and gram-negative bacteria, yeast and fungi

What are the applications of Application

Rabeprazole Sodium Salt is a proton pump inhibitor

Definition

ChEBI: Rabeprazole sodium is an organic sodium salt. It contains a rabeprazole(1-).

brand name

Aciphex (Eisai Medical Research) .

General Description

Rabeprazole sodium, 2[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole sodium salt (Aciphex), is a white toslightly yellowish white solid. It is very soluble in water andmethanol, freely soluble in ethanol, chloroform, and ethyl acetate,and insoluble in ether and hexane. Rabeprazole is aweak base (pyridine N, pKa 4.53) and a weak acid (benzimidazoleN-H, pKa 0.62), faciliting sodium salt formation.
Rabeprazole sodium is formulated as enteric-coated,delayed-release tablets to allow the drug to pass throughthe stomach relatively intact. After oral administration of20-mg peak plasma concentrations (Cmax) occur over arange of 2 to 5 hours (Tmax). Absolute bioavailability for a20-mg oral tablet of rabeprazole (vs. IV administration) isapproximately 52%. The plasma half-life ofrabeprazole ranges from 1 to 2 hours. The effects of foodon the absorption of rabeprazole have not been evaluated.Rabeprazole is 96% bound to human plasma proteins.Rabeprazole is extensively metabolized in the liver. Thethioether and sulfone are the primary metabolites measuredin human plasma resulting from CYP3A oxidation.Additionally, desmethyl rabeprazole is formed via the actionof CYP2C19. Approximately 90% of the drug is eliminatedin the urine, primarily as thioether carboxylic acidand its glucuronide and mercapturic acid metabolites. Theremainder of the dose is recovered in the feces. No unchangedrabeprazole is excreted in the urine or feces.

Biochem/physiol Actions

Rabeprazole sodium is gastric proton pump inhibitor. It suppresses the production of acid in the stomach by inhibiting the gastric H+/K+ATPase (hydrogen-potassium adenosine triphosphatase) at the secretory surface of the gastric parietal cell. Rabeprazole sodium has been used clinically to treat acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevent gastroinetestinal bleeds associated with NSAID use.

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.

Metabolism

Rabeprazole is mainly metabolised via nonenzymatic reduction and, to a lesser extent, via the cytochrome P450 isoenzymes CYP2C19 and CYP3A4. Metabolites are excreted principally in the urine (about 90%) with the remainder in the faeces.

Properties of Rebeprazole sodium

Melting point: 140-141°C dec.
storage temp.  -20°C
solubility  H2O: soluble10mg/mL (clear solution)
form  powder
color  white to beige
Merck  14,8089
Stability: Hygroscopic

Safety information for Rebeprazole sodium

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H413:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P273:Avoid release to the environment.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P501:Dispose of contents/container to..…

Computed Descriptors for Rebeprazole sodium

InChIKey KRCQSTCYZUOBHN-UHFFFAOYSA-N

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