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 32 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23350044	Inhibitor 8228

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 8360	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 8360	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 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20973lbl.pdf	Primary	Approved 8360	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
4-day triple therapy with rabeprazole, amoxicillin and clarithromycin in the eradication of Helicobacter pylori in patients with peptic ulcer disease--A pilot study.	2001 Apr	11367976
Effects of pirenzepine, omeprazole, lansoprazole, and rabeprazole on human neutrophil functions.	2001 Apr	11339790
[H2 receptor antagonists and proton pump inhibitors: principles and rules of use].	2001 Apr 15	11387678
Dyspepsia: challenges in diagnosis and selection of treatment.	2001 Aug	11558854
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
A randomized open trial for comparison of proton pump inhibitors, omeprazole versus rabeprazole, in dual therapy for Helicobacter pylori infection in relation to CYP2C19 genetic polymorphism.	2001 Jul	11446878
Cost-effectiveness of proton-pump inhibitors for maintenance therapy of erosive reflux esophagitis.	2001 Jul 15	11471482
Strategy for retreatment of therapeutic failure of eradication of Helicobacter pylori infection.	2001 Jun	11422612
Inhibitory action of a novel proton pump inhibitor, rabeprazole, and its thioether derivative against the growth and motility of clarithromycin-resistant Helicobacter pylori.	2001 Jun	11422467
Laryngopharyngeal reflux symptoms improve before changes in physical findings.	2001 Jun	11404607
Pharmacodynamic effects and kinetic disposition of rabeprazole in relation to CYP2C19 genotypes.	2001 Jun	11380317
New-generation proton pump inhibitors: overcoming the limitations of early-generation agents.	2001 May	11430508
Proton pump inhibitors and their drug interactions: an evidence-based approach.	2001 May	11396546
Systematic review of proton pump inhibitors for the acute treatment of reflux oesophagitis.	2001 Nov	11683686
Proton pump inhibition. An effective, safe approach to GERD management.	2001 Oct	11868428
[Modern means of anti-Helicobacter therapy].	2001 Oct	11764485
Decreasing oesophageal acid exposure in patients with GERD: a comparison of rabeprazole and omeprazole.	2001 Sep	11552904
[Effectiveness of pariet (rabeprazole) in the treatment of gastroesophageal reflux disease (at the reflux-esophagitis stage)].	2002	12271586
[Regeneration of the esophagus epitheliocytes. Evaluation of pariet efficacy in the treatment of patients with reflux esophagitis].	2002	12046386
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
Levofloxacin based regimens for the eradication of Helicobacter pylori.	2002 Dec	12468950
Treatment and management of Helicobacter pylori infection.	2002 Dec	12441037
The pharmacology and clinical relevance of proton pump inhibitors.	2002 Dec	12441035
[Minocycline-containing eradication therapy for patients with clarithromycin-resistant Helicobacter pylori infection].	2002 Feb	11979825
[Dual therapy for Helicobacter pylori resistance to anti microbial agents].	2002 Feb	11979819
Treatment with a proton pump inhibitor promotes corpus gastritis in patients with Helicobacter pylori-infected antrum-predominant gastritis.	2002 Jan	11856091
Effects of lansoprazole and rabeprazole on tacrolimus blood concentration: case of a renal transplant recipient with CYP2C19 gene mutation.	2002 Jan 27	11821750
Gateways to clinical trials.	2002 Jan-Feb	11980386
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
Primary hyperparathyroidism with duodenal ulcer and H. pylori infection.	2002 May	12058887
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
Drug interaction of tacrolimus and proton pump inhibitors in renal transplant recipients with CYP2C19 gene mutation.	2002 Nov	12431607
Effect of different probiotic preparations on anti-helicobacter pylori therapy-related side effects: a parallel group, triple blind, placebo-controlled study.	2002 Nov	12425542
Restoration of acid secretion following treatment with proton pump inhibitors.	2002 Nov	12404233
Eradication rates of clarithromycin-resistant Helicobacter pylori using either rabeprazole or lansoprazole plus amoxicillin and clarithromycin.	2002 Nov	12390102
A new serum antibody test kit (E plate) for evaluation of Helicobacter pylori eradication.	2002 Oct	12412995
Sequential eradicating therapy: a treatment that does not discriminate Helicobacter pylori strains in patients with nonulcer dyspepsia?	2002 Oct	12385470
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
Rabeprazole: pharmacokinetics and pharmacokinetic drug interactions.	2002 Sep	12369444

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 `Wed Jul 05 23:13:04 UTC 2023` Edited by `admin` on `Wed Jul 05 23:13:04 UTC 2023`
Record UNII	32828355LL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RABEPRAZOLE

Official Name

English

LY-307640

Code

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