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
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)
DescriptionCurator's Comment: description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20973lbl.pdf
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 |
|---|---|---|---|
Target ID: CHEMBL2095173 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ACIPHEX Approved UseACIPHEX 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 Date1999 |
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| Primary | ACIPHEX Approved UseACIPHEX 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 Date1999 |
|||
| Primary | ACIPHEX Approved UseACIPHEX 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 Date1999 |
Cmax
| Value | Dose | Co-administered | 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 |
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 |
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 | Co-administered | 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 |
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 |
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 |
T1/2
| Value | Dose | Co-administered | 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 |
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 |
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: 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: 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: Page: p.978 |
unhealthy, 41 n = 20 Health Status: unhealthy Condition: Gastroesophageal reflux disease Age Group: 41 Sex: M+F Population Size: 20 Sources: 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: 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: Page: p.1337 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Pariet in eradication therapy plans]. | 2002 |
|
| [Seven-day antihelicobacter therapy of duodenal ulcer associated with Helicobacter pylori and prospects for treating patients]. | 2002 |
|
| [Effectiveness of pariet (rabeprazole) in the treatment of gastroesophageal reflux disease (at the reflux-esophagitis stage)]. | 2002 |
|
| Patients have treatment preferences: a multicentre, double-blind, crossover study comparing rabeprazole and omeprazole. | 2002 |
|
| [Regeneration of the esophagus epitheliocytes. Evaluation of pariet efficacy in the treatment of patients with reflux esophagitis]. | 2002 |
|
| [Inhibitors of proton pump in the treatment of non-ulcer functional dyspepsia of the reflux-like type]. | 2002 |
|
| Rabeprazole: quest for the best PPI. | 2002 |
|
| The effects of rabeprazole on parietal cells and enterochromaffin-like cells in rats: a comparison with omeprazole. | 2002 |
|
| [Regeneration of the gastric epitheliocytes during treatment of duodenal ulcer with pariet]. | 2002 Apr |
|
| Proton pump inhibitor modifies inflammatory reaction in human gastric mucosa infected by Helicobacter pylori. | 2002 Apr |
|
| Levofloxacin based regimens for the eradication of Helicobacter pylori. | 2002 Dec |
|
| Treatment and management of Helicobacter pylori infection. | 2002 Dec |
|
| The pharmacology and clinical relevance of proton pump inhibitors. | 2002 Dec |
|
| [Cause and prevention of nocturnal gastric acid breakthrough]. | 2002 Feb |
|
| [Proton pump inhibitors: Rabeprazole]. | 2002 Feb |
|
| [Continuation of acid suppression therapy after H. pylori eradication]. | 2002 Feb |
|
| [Minocycline-containing eradication therapy for patients with clarithromycin-resistant Helicobacter pylori infection]. | 2002 Feb |
|
| [Second line treatment regimen of PPI + AMPC + MNZ for patients with clarithromycin-resistant Helicobacter pylori infection]. | 2002 Feb |
|
| [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 |
|
| [Proton pump inhibitor-based quadruple therapy regimen for Helicobacter pylori infection]. | 2002 Feb |
|
| [Dual therapy for Helicobacter pylori resistance to anti microbial agents]. | 2002 Feb |
|
| [Pharma-clinics medication of the month. Rabeprazole (Pariet)]. | 2002 Jan |
|
| Gateways to clinical trials. | 2002 Jan-Feb |
|
| [Evaluation of efficacy, safety and tolerability rabeprazole in treatment of acid-peptic diseases ]. | 2002 Jan-Mar |
|
| Rabeprazole. | 2002 Jan-Mar |
|
| Proton pump inhibitors--differences emerge in hepatic metabolism. | 2002 Jul |
|
| Impact of proton pump inhibitor utilization patterns on gastroesophageal reflux disease-related costs. | 2002 Jul |
|
| Effects of rabeprazole, 20 mg, or esomeprazole, 20 mg, on 24-h intragastric pH and serum gastrin in healthy subjects. | 2002 Jul |
|
| The efficacy of lafutidine in improving preoperative gastric fluid property: a comparison with ranitidine and rabeprazole. | 2002 Jul |
|
| Proton pump inhibitors: an update. | 2002 Jul 15 |
|
| Are proton pump inhibitors the first choice for acute treatment of gastric ulcers? A meta analysis of randomized clinical trials. | 2002 Jul 15 |
|
| Polymorphism of CYP2C19 and gastric emptying in patients with proton pump inhibitor-resistant gastric ulcers. | 2002 Jul-Aug |
|
| Rabeprazole in nonerosive gastroesophageal reflux disease: a randomized placebo-controlled trial. | 2002 Jun |
|
| Single vs. double dose of a proton pump inhibitor in triple therapy for Helicobacter pylori eradication: a meta-analysis. | 2002 Jun |
|
| A randomized, double-blind, comparative study of standard-dose rabeprazole and high-dose omeprazole in gastro-oesophageal reflux disease. | 2002 Mar |
|
| Integrated acidity and rabeprazole pharmacology. | 2002 Mar |
|
| Primary hyperparathyroidism with duodenal ulcer and H. pylori infection. | 2002 May |
|
| Combination drug therapy for gastroesophageal reflux disease. | 2002 May |
|
| A modification of the quininium resin test for assessing gastric acidity. | 2002 May |
|
| Rabeprazole improves health-related quality of life in patients with erosive gastroesophageal reflux disease. | 2002 Nov |
|
| Drug interaction of tacrolimus and proton pump inhibitors in renal transplant recipients with CYP2C19 gene mutation. | 2002 Nov |
|
| Effect of different probiotic preparations on anti-helicobacter pylori therapy-related side effects: a parallel group, triple blind, placebo-controlled study. | 2002 Nov |
|
| Restoration of acid secretion following treatment with proton pump inhibitors. | 2002 Nov |
|
| Eradication rates of clarithromycin-resistant Helicobacter pylori using either rabeprazole or lansoprazole plus amoxicillin and clarithromycin. | 2002 Nov |
|
| A new serum antibody test kit (E plate) for evaluation of Helicobacter pylori eradication. | 2002 Oct |
|
| Sequential eradicating therapy: a treatment that does not discriminate Helicobacter pylori strains in patients with nonulcer dyspepsia? | 2002 Oct |
|
| Effects of rabeprazole, lansoprazole and omeprazole on intragastric pH in CYP2C19 extensive metabolizers. | 2002 Oct |
|
| Gateways to Clinical Trials. | 2002 Sep |
|
| [The short term effect of rabeprazol versus omeprazole on symptom relief of duodenal ulcer]. | 2002 Sep |
|
| Rabeprazole: pharmacokinetics and pharmacokinetic drug interactions. | 2002 Sep |
Sample Use Guides
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
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.
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| Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175525
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LIVERTOX |
NBK548154
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WHO-ATC |
A02BC54
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NDF-RT |
N0000000147
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WHO-ATC |
A02BC04
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WHO-VATC |
QA02BC04
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NCI_THESAURUS |
C29723
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SUB10229MIG
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DTXSID3044122
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7112
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100000080304
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Rabeprazole
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7290
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C063129
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DB01129
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RABEPRAZOLE
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8768
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117976-89-3
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5029
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7321
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m9476
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C29410
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114979
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32828355LL
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2350
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CHEMBL1219
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32828355LL
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METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PRODRUG)
METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
