RABEPRAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H21N3O3S
Molecular Weight	359.443
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCCCOC1=CC=NC(C[S+]([O-])C2=NC3=C(N2)C=CC=C3)=C1C

InChI

InChIKey=YREYEVIYCVEVJK-UHFFFAOYSA-N

InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)

HIDE SMILES / InChI

Molecular Formula	C18H21N3O3S
Molecular Weight	359.443
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10551440
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20973lbl.pdf

Rabeprazole sodium was discovered by Eisai Co., Ltd. Janssen Pharmaceutica N.V. and Eisai Co., Ltd. have a strategic alliance in which Eisai and Janssen-Cilag co-promote the drug in Germany and the U.K. In the US rabeprazole sodium is co-promoted under the brand name AcipHex by Eisai Inc. and Janssen Pharmaceutica Inc. Pariet is available through Janssen-Cilag in most other countries excluding Japan and some Asian countries. Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. Rabeprazole is a prodrug and is converted to the active sulphenamide form in the acid environment of the parietal cells. Rabeprazole is used to heal and maintain the healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD), for healing Duodenal Ulcers, and for treatment of pathological hypersecretory conditions such as Zollinger-Ellison Syndrome. Rabeprazole suppresses gastric acid secretion by inhibiting the gastric H+, K+ATPase at the secretory surface of the gastric parietal cell and does not exhibit anticholinergic or histamine H2-receptor antagonist properties. Because this enzyme is regarded as the acid (proton) pump within the parietal cell, rabeprazole has been characterized as a gastric proton-pump inhibitor which blocks the final step of gastric acid secretion. In gastric parietal cells, rabeprazole is protonated, accumulates, and is transformed to an active sulfonamide.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Potassium-transporting ATPase 30 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23350044	Inhibitor 8146

Conditions

Condition	Modality	Highest Phase	Product
Erosive or ulcerative gastroesophageal reflux disease 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20973lbl.pdf	Primary	Approved 8307	ACIPHEX Approved Use ACIPHEX is a proton-pump inhibitor (PPI) indicated in adults for: Healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD) ( ) 1.1 Maintenance of Healing of Erosive or Ulcerative GERD ( ) 1.2 Treatment of Symptomatic GERD ( ) 1.3 Healing of Duodenal Ulcers ( ) 1.4 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence ( ) Helicobacter pylori 1.5 Treatment of Pathological Hypersecretory Conditions, Including Zollinger-Ellison Syndrome ( ) 1.6 In adolescent patients 12 years of age and older for: Short-term treatment of Symptomatic GERD ( ) 1.7 In pediatric patients 1 to 11 years of age for: Treatment of GERD ( ) 1.8 1.1 Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for short-term (4 to 8 weeks) treatment in the healing and symptomatic relief of erosive or ulcerative gastroesophageal reflux disease (GERD). For those patients who have not healed after 8 weeks of treatment, an additional 8-week course of ACIPHEX may be considered. 1.2 Maintenance of Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for maintaining healing and reduction in relapse rates of heartburn symptoms in patients with erosive or ulcerative gastroesophageal reflux disease (GERD Maintenance). Controlled studies do not extend beyond 12 months. 1.3 Treatment of Symptomatic GERD in Adults ACIPHEX is indicated for the treatment of daytime and nighttime heartburn and other symptoms associated with GERD in adults 1.4 Healing of Duodenal Ulcers in Adults ACIPHEX is indicated for short-term (up to four weeks) treatment in the healing and symptomatic relief of duodenal ulcers. Most patients heal within four weeks. 1.5 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence in Adults Helicobacter pylori ACIPHEX in combination with amoxicillin and clarithromycin as a three drug regimen, is indicated for the treatment of patients with infection and duodenal ulcer disease (active or history within the past 5 years) to eradicate . Eradication of has been shown to reduce the risk of duodenal ulcer recurrence [ and Launch Date 9.3502079E11
Duodenal ulcer 41 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20973lbl.pdf	Primary	Approved 8307	ACIPHEX Approved Use ACIPHEX is a proton-pump inhibitor (PPI) indicated in adults for: Healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD) ( ) 1.1 Maintenance of Healing of Erosive or Ulcerative GERD ( ) 1.2 Treatment of Symptomatic GERD ( ) 1.3 Healing of Duodenal Ulcers ( ) 1.4 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence ( ) Helicobacter pylori 1.5 Treatment of Pathological Hypersecretory Conditions, Including Zollinger-Ellison Syndrome ( ) 1.6 In adolescent patients 12 years of age and older for: Short-term treatment of Symptomatic GERD ( ) 1.7 In pediatric patients 1 to 11 years of age for: Treatment of GERD ( ) 1.8 1.1 Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for short-term (4 to 8 weeks) treatment in the healing and symptomatic relief of erosive or ulcerative gastroesophageal reflux disease (GERD). For those patients who have not healed after 8 weeks of treatment, an additional 8-week course of ACIPHEX may be considered. 1.2 Maintenance of Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for maintaining healing and reduction in relapse rates of heartburn symptoms in patients with erosive or ulcerative gastroesophageal reflux disease (GERD Maintenance). Controlled studies do not extend beyond 12 months. 1.3 Treatment of Symptomatic GERD in Adults ACIPHEX is indicated for the treatment of daytime and nighttime heartburn and other symptoms associated with GERD in adults 1.4 Healing of Duodenal Ulcers in Adults ACIPHEX is indicated for short-term (up to four weeks) treatment in the healing and symptomatic relief of duodenal ulcers. Most patients heal within four weeks. 1.5 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence in Adults Helicobacter pylori ACIPHEX in combination with amoxicillin and clarithromycin as a three drug regimen, is indicated for the treatment of patients with infection and duodenal ulcer disease (active or history within the past 5 years) to eradicate . Eradication of has been shown to reduce the risk of duodenal ulcer recurrence [ and Launch Date 9.3502079E11
Zollinger-Ellison syndrome 16 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20973lbl.pdf	Primary	Approved 8307	ACIPHEX Approved Use ACIPHEX is a proton-pump inhibitor (PPI) indicated in adults for: Healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD) ( ) 1.1 Maintenance of Healing of Erosive or Ulcerative GERD ( ) 1.2 Treatment of Symptomatic GERD ( ) 1.3 Healing of Duodenal Ulcers ( ) 1.4 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence ( ) Helicobacter pylori 1.5 Treatment of Pathological Hypersecretory Conditions, Including Zollinger-Ellison Syndrome ( ) 1.6 In adolescent patients 12 years of age and older for: Short-term treatment of Symptomatic GERD ( ) 1.7 In pediatric patients 1 to 11 years of age for: Treatment of GERD ( ) 1.8 1.1 Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for short-term (4 to 8 weeks) treatment in the healing and symptomatic relief of erosive or ulcerative gastroesophageal reflux disease (GERD). For those patients who have not healed after 8 weeks of treatment, an additional 8-week course of ACIPHEX may be considered. 1.2 Maintenance of Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for maintaining healing and reduction in relapse rates of heartburn symptoms in patients with erosive or ulcerative gastroesophageal reflux disease (GERD Maintenance). Controlled studies do not extend beyond 12 months. 1.3 Treatment of Symptomatic GERD in Adults ACIPHEX is indicated for the treatment of daytime and nighttime heartburn and other symptoms associated with GERD in adults 1.4 Healing of Duodenal Ulcers in Adults ACIPHEX is indicated for short-term (up to four weeks) treatment in the healing and symptomatic relief of duodenal ulcers. Most patients heal within four weeks. 1.5 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence in Adults Helicobacter pylori ACIPHEX in combination with amoxicillin and clarithromycin as a three drug regimen, is indicated for the treatment of patients with infection and duodenal ulcer disease (active or history within the past 5 years) to eradicate . Eradication of has been shown to reduce the risk of duodenal ulcer recurrence [ and Launch Date 9.3502079E11

C_max

Value	Dose	Analyte	Population
1.54 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30321480	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.406 μg/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/28294690	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.5 μg/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/28294690	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2.15 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30321480	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.809 μg × h/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/28294690	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
5.212 μg × h/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/28294690	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
3.46 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30321480	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.02 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/28294690	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
1.21 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/28294690	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	RABEPRAZOLE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
40 mg single, oral Recommended Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9701531 Page: p.670	healthy, 22.5 ± 3.9 n = 8 Health Status: healthy Age Group: 22.5 ± 3.9 Sex: M Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/9701531 Page: p.670	Sources: https://pubmed.ncbi.nlm.nih.gov/9701531 Page: p.670
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9354209 Page: p.978	unhealthy, 41 n = 20 Health Status: unhealthy Condition: Gastroesophageal reflux disease Age Group: 41 Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/9354209 Page: p.978	Sources: https://pubmed.ncbi.nlm.nih.gov/9354209 Page: p.978
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12094846 Page: p.1337	unhealthy, 45.5 n = 68 Health Status: unhealthy Condition: Gastroesophageal reflux disease Age Group: 45.5 Sex: M+F Population Size: 68 Sources: https://pubmed.ncbi.nlm.nih.gov/12094846 Page: p.1337	Sources: https://pubmed.ncbi.nlm.nih.gov/12094846 Page: p.1337

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8768	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8768
ChemicalBook	CB3680731	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3680731
MolPort	MolPort-005-935-061	https://www.molport.com/shop/molecule-link/MolPort-005-935-061
eMolecules	601413	https://www.emolecules.com/cgi-bin/more?vid=601413

PubMed

Title	Date	PubMed
Rabeprazole: an update of its use in acid-related disorders.	2001	11772142
Relative efficacies of gastric proton-pump inhibitors on a milligram basis: desired and undesired SH reactions. Impact of chirality.	2001	11768559
Efficacy of Helicobacter pylori eradication therapies: a single centre observational study.	2001	11545677
[Pariet in current patterns of eradication of Helicobacter pylori infection].	2001 Apr	11547668
Dyspepsia: challenges in diagnosis and selection of treatment.	2001 Aug	11558854
Rabeprazole-based 3-day and 7-day triple therapy vs. omeprazole-based 7-day triple therapy for the treatment of Helicobacter pylori infection.	2001 Dec	11736727
[Selection of antibiotics and planning of eradication for H. pylori infection].	2001 Feb	11218403
Healing and relapse rates in gastroesophageal reflux disease treated with the newer proton-pump inhibitors lansoprazole, rabeprazole, and pantoprazole compared with omeprazole, ranitidine, and placebo: evidence from randomized clinical trials.	2001 Jul	11519776
Strategy for retreatment of therapeutic failure of eradication of Helicobacter pylori infection.	2001 Jun	11422612
New-generation proton pump inhibitors: overcoming the limitations of early-generation agents.	2001 May	11430508
Effects of CYP2C19 gene polymorphism on cure rates for Helicobacter pylori infection by triple therapy with proton pump inhibitor (omeprazole or rabeprazole), amoxycillin and clarithromycin in Japan.	2001 Nov	11785712
[Comparative antisecretory activity of famotidine, omeprazole, and rabeprazole (pariet) in ulcer disease based on daily pH-monitoring].	2001 Sep	11668793
Efficacy of triple therapy with rabeprazole for Helicobacter pylori infection and CYP2C19 genetic polymorphism.	2001 Sep	11552922
Decreasing oesophageal acid exposure in patients with GERD: a comparison of rabeprazole and omeprazole.	2001 Sep	11552904
[Comparative study of proton pump inhibitors].	2001 Sep 9	11680100
[Pariet in eradication therapy plans].	2002	12353394
[Seven-day antihelicobacter therapy of duodenal ulcer associated with Helicobacter pylori and prospects for treating patients].	2002	12353382
[Effectiveness of pariet (rabeprazole) in the treatment of gastroesophageal reflux disease (at the reflux-esophagitis stage)].	2002	12271586
Rabeprazole: quest for the best PPI.	2002	11931540
The effects of rabeprazole on parietal cells and enterochromaffin-like cells in rats: a comparison with omeprazole.	2002	11931530
[Regeneration of the gastric epitheliocytes during treatment of duodenal ulcer with pariet].	2002 Apr	12046531
Proton pump inhibitor modifies inflammatory reaction in human gastric mucosa infected by Helicobacter pylori.	2002 Apr	11966546
Levofloxacin based regimens for the eradication of Helicobacter pylori.	2002 Dec	12468950
[Continuation of acid suppression therapy after H. pylori eradication].	2002 Feb	11979841
[High dose dual PPI/AMPC therapy for the treatment of Helicobacter pylori infection after failure of usual standard triple PPI/AMPC/CAM therapy: CYP2C19 polymorphism].	2002 Feb	11979823
[Proton pump inhibitor-based quadruple therapy regimen for Helicobacter pylori infection].	2002 Feb	11979821
[Dual therapy for Helicobacter pylori resistance to anti microbial agents].	2002 Feb	11979819
[Pharma-clinics medication of the month. Rabeprazole (Pariet)].	2002 Jan	11899500
Treatment with a proton pump inhibitor promotes corpus gastritis in patients with Helicobacter pylori-infected antrum-predominant gastritis.	2002 Jan	11856091
[Evaluation of efficacy, safety and tolerability rabeprazole in treatment of acid-peptic diseases ].	2002 Jan-Mar	12184168
Proton pump inhibitors--differences emerge in hepatic metabolism.	2002 Jul	12236477
Impact of proton pump inhibitor utilization patterns on gastroesophageal reflux disease-related costs.	2002 Jul	12181872
Effects of rabeprazole, 20 mg, or esomeprazole, 20 mg, on 24-h intragastric pH and serum gastrin in healthy subjects.	2002 Jul	12144580
Measuring symptom distress and health-related quality of life in clinical trials of gastroesophageal reflux disease treatment: further validation of the Gastroesophageal Reflux Disease Symptom Assessment Scale (GSAS).	2002 Jul	12141813
Randomized open trial for comparison of proton pump inhibitors in triple therapy for Helicobacter pylori infection in relation to CYP2C19 genotype.	2002 Jul	12121503
The efficacy of lafutidine in improving preoperative gastric fluid property: a comparison with ranitidine and rabeprazole.	2002 Jul	12088958
Proton pump inhibitors: an update.	2002 Jul 15	12152963
Are proton pump inhibitors the first choice for acute treatment of gastric ulcers? A meta analysis of randomized clinical trials.	2002 Jul 15	12119060
Polymorphism of CYP2C19 and gastric emptying in patients with proton pump inhibitor-resistant gastric ulcers.	2002 Jul-Aug	12235924
Rabeprazole in nonerosive gastroesophageal reflux disease: a randomized placebo-controlled trial.	2002 Jun	12094846
Review article: rabeprazole-based therapy in Helicobacter pylori eradication.	2002 Mar	11849125
Primary hyperparathyroidism with duodenal ulcer and H. pylori infection.	2002 May	12058887
Combination drug therapy for gastroesophageal reflux disease.	2002 May	11978171
A modification of the quininium resin test for assessing gastric acidity.	2002 May	11966494
Rabeprazole improves health-related quality of life in patients with erosive gastroesophageal reflux disease.	2002 Nov	12452397
Effect of different probiotic preparations on anti-helicobacter pylori therapy-related side effects: a parallel group, triple blind, placebo-controlled study.	2002 Nov	12425542
A new serum antibody test kit (E plate) for evaluation of Helicobacter pylori eradication.	2002 Oct	12412995
Effects of rabeprazole, lansoprazole and omeprazole on intragastric pH in CYP2C19 extensive metabolizers.	2002 Oct	12269976
Gateways to Clinical Trials.	2002 Sep	12428432
[The short term effect of rabeprazol versus omeprazole on symptom relief of duodenal ulcer].	2002 Sep	12421488

Patents

Sample Use Guides

In Vivo Use Guide

Erosive or Ulcerative Gastroesophageal Reflux Disease: 20 mg delayed-release tablet to be taken once daily for four to eight weeks. Duodenal Ulcers: 20 mg delayed-release tablet to be taken once daily after the morning meal for a period up to four weeks. Pathological Hypersecretory Conditions Including Zollinger-Ellison Syndrome: The recommended adult oral starting dose is 60 mg once a day. Doses should be adjusted to individual patient needs and should continue for as long as clinically indicated. Some patients may require divided doses. Doses up to 100 mg QD and 60 mg BID have been administered

Route of Administration: Oral

In Vitro Use Guide

The MICs of rabeprazole sodium (RPZ) against 133 clinical Helicobacter pylori strains revealed a higher degree of activity. The 133 H. pylori strains tested were recent clinical isolates from different patients with chronic gastritis and gastric and/or duodenal ulcer. The final concentrations prepared in the wells of the microplates were from 0.031 to 64 μg/ml for RPZ.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 18:01:30 UTC 2022` Edited by `admin` on `Fri Dec 16 18:01:30 UTC 2022`
Record UNII	32828355LL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RABEPRAZOLE

Official Name

English

LY-307640

Common Name

English

E-3810 (PPI)

Code

English

1H-BENZIMIDAZOLE, 2-(((4-(3-METHOXYPROPOXY)-3-METHYL-2-PYRIDINYL)METHYL)SULFINYL)-

Systematic Name

English

E3810

Code

English

rabeprazole [INN]

Common Name

English

LY307640

Code

English

RABEPRAZOLE [VANDF]

Common Name

English

RABEPRAZOLE [MI]

Common Name

English

PARIPRAZOLE

Common Name

English

Rabeprazole [WHO-DD]

Common Name

English

ERALOC

Brand Name

English

RABEPRAZOLE [HSDB]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175525