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Rabeprazole sodium

Rabeprazole sodium structure

CAS No:
117976-90-6
Formula:
C18H21N3O3S.Na
Chemical Name:
Rabeprazole sodium
Synonyms:
1H-Benzimidazole,2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-,sodium salt (1:1);1H-Benzimidazole,2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-,sodium salt;E 3810;LY 307640 sodium;Rabeprazole sodium;Pariprazole;Pariet;Aciphex;2-[[[4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methyl]sulfinyl]-1H-benzimidazole sodium salt;Rabicip;Pepcia;Razo;129982-41-8;226904-80-9;1017795-22-0
Categories:
Active Pharmaceutical Ingredients > Digestive System Drugs

Description

Rebeprazole sodium is White Crystalline Solid 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+-a

Rabeprazole sodium is an organic sodium salt. It contains a rabeprazole(1-).|Rabeprazole is a proton pump inhibitor (PPI) and a potent inhibitor of gastric acidity used in the therapy of gastroesophageal reflux and peptic ulcer disease. Rabeprazole therapy is associated with a low rate of transient and asymptomatic serum aminotransferase elevations and is a rare cause of clinically apparent liver injury.|A 4-(3-methoxypropoxy)-3-methylpyridinyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.

Rabeprazole sodium Basic Attributes

Molecular Weight：

381.42

Exact Mass：

381.112305

EC Number：

222-630-7

DSSTox ID：

DTXSID3044205

HScode：

2933399090

Characteristics

PSA：

81.5

XLogP3：

3.48420

Appearance：

white to beige

Density：

0.45~0.55 g/ml

Melting Point：

140-141 °C (decomp)

Boiling Point：

603.9°C at 760 mmHg

Flash Point：

319.1ºC

Water Solubility：

H2O: soluble10mg/mL (clear solution)

Storage Conditions：

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Vapor Pressure：

2.2X10-15 mm Hg at 25 deg C /Estimated/

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

Precautionary statement(s)：

P260, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P309+P311, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (71.43%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P309+P311, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 7 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hepatotoxicity：

Despite its wide use, rabeprazole has only rarely been associated with hepatic injury. In large scale, long term trials of rabeprazole, serum ALT elevations occurred in less than 1% of patients and at rates similar to those with placebo or comparator drugs. In large case series of drug induced liver injury, rabeprazole has accounted for few instances of symptomatic acute liver injury. Only a few cases of clinically apparent liver disease due to rabeprazole have been published and the characteristics of the injury have not been well defined, but appear to be similar to the features of hepatic injury associated with other proton pump inibitors. Clinically apparent liver injury due to proton pump inhibitors typically arises within the first 4 weeks of treatment with symptoms of jaundice, nausea and fatigue and a hepatocellular or mixed pattern of serum enzyme elevations. Recovery is typically rapid upon withdrawal of the agent. Rash, fever and eosinophilia are rare, as is autoantibody formation. Instances of recurrence on rechallenge have been reported.

Drug Information

Drug Indication：

Treatment of duodenal ulcer, Treatment of gastric ulcer, Treatment of gastro-oesophageal reflux disease, Treatment of Helicobacter pylori in patients with peptic ulcer disease, Treatment of Zollinger-Ellison syndrome

LiverTox Summary：

Rabeprazole is a proton pump inhibitor (PPI) and a potent inhibitor of gastric acidity used in the therapy of gastroesophageal reflux and peptic ulcer disease. Rabeprazole therapy is associated with a low rate of transient and asymptomatic serum aminotransferase elevations and is a rare cause of clinically apparent liver injury.

Drug Classes：

Antiulcer Agents

MeSH：

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)|Compounds that inhibit H(+)-K(+)-EXCHANGING ATPASE. They are used as ANTI-ULCER AGENTS and sometimes in place of HISTAMINE H2 ANTAGONISTS for GASTROESOPHAGEAL REFLUX. (See all compounds classified as Proton Pump Inhibitors.)

MeSH Entry Terms：

1H-Benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, sodium salt

Rabeprazole sodium Use and Manufacturing

Uses

A partially reversible gastric proton pump inhibitor

Use Classification：

Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:381.4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:381.11230696
Monoisotopic Mass:381.11230696
Topological Polar Surface Area:81.5
Heavy Atom Count:26
Complexity:446
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Rabeprazole sodium is a drug that inhibits secretion and is a substitute for benzimidazole. It has no anticholinergic and anti-H2 histamine properties. It blocks the production of gastric acid by inhibiting H/K-ATPase on the surface of gastric parietal cells. This effect is dose-related. Its inhibitory effect on gastric acid secretion can be slightly enhanced with increasing doses, but can reach a stable level after three days. Even after discontinuation of the drug, this stable level can be maintained for 2 to 3 days.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Rabeprazole Sodium Enteric-coated Tablets
Ingredients	The main ingredient of this product is rabeprazole sodium. Chemical name: 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-benzimidazole sodium. Molecular formula: C18H20N3O3SNa. Molecular weight: 381.43.
Indication	Rabeprazole sodium is a member of the proton pump inhibitor (PPI) class of compounds that is metabolized by the cytochrome P450 (CYP450) hepatic drug metabolism system. Studies in healthy subjects have shown that there is no clinically significant interaction between rabeprazole sodium and other drugs metabolized by the CYP450 system, such as warfarin, phenytoin, theophylline or diazepam. Rabeprazole sodium can inhibit gastric acid secretion for a long time. This product interacts with compounds that are absorbed depending on pH, so potential interactions should be investigated. The simultaneous administration of rabeprazole sodium to normal subjects resulted in a 33% decrease in ketoconazole levels and a 22% increase in digoxin levels. Therefore, individual patient testing is required to determine whether dose adjustment is required when these drugs are taken with this product.
Specifications	20mg
Manufacturer	Double-Crane Pharmaceutical(Hainan) Co., Ltd.

Rabeprazole Sodium Enteric-coated Capsules
Ingredients	The main ingredient of this product is rabeprazole sodium.
Indication	Rabeprazole is metabolized by the cytochrome P450 (CYP450) metabolic enzyme system. Studies in healthy subjects have shown that rabeprazole sodium has no significant clinical interactions with other drugs metabolized by the CYP450 system. Rabeprazole sodium can produce a sustained inhibitory effect on gastric acid secretion. Because rabeprazole sodium reduces acidity, it interacts with drugs whose absorption is related to gastric pH. For example, if normal subjects take ketoconazole and 20 mg of rabeprazole sodium simultaneously daily, the bioavailability of ketoconazole will be reduced by approximately 30%; taking digoxin at the same time will increase the AUC and Cmax values of digoxin by 19% and 29%, respectively. Therefore, patients should be monitored when taking the above drugs and rabeprazole sodium at the same time. Rabeprazole
Specifications	10mg
Manufacturer	Livzon (GROUP) Pharmaceutical FACTORY

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METROCHEM API PRIVATE LTD

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