Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H20N3O3S.Na |
| Molecular Weight | 381.424 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].COCCCOC1=CC=NC(C[S+]([O-])C2=NC3=C([N-]2)C=CC=C3)=C1C
InChI
InChIKey=KRCQSTCYZUOBHN-UHFFFAOYSA-N
InChI=1S/C18H20N3O3S.Na/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;/q-1;+1
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 |
|||
| 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 |
|---|---|---|
| Relative efficacies of gastric proton-pump inhibitors on a milligram basis: desired and undesired SH reactions. Impact of chirality. | 2001 |
|
| [A new blocker of proton pump pariet: pharmacological properties and effectiveness of clinical application]. | 2001 |
|
| [Pariet in current patterns of eradication of Helicobacter pylori infection]. | 2001 Apr |
|
| Effects of pirenzepine, omeprazole, lansoprazole, and rabeprazole on human neutrophil functions. | 2001 Apr |
|
| [H2 receptor antagonists and proton pump inhibitors: principles and rules of use]. | 2001 Apr 15 |
|
| Dyspepsia: challenges in diagnosis and selection of treatment. | 2001 Aug |
|
| Helicobacter pylori eradication: do we have another ace up our sleeve? | 2001 Dec |
|
| 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 |
|
| [Selection of antibiotics and planning of eradication for H. pylori infection]. | 2001 Feb |
|
| The effect of oral administration of Lactobacillus GG on antibiotic-associated gastrointestinal side-effects during Helicobacter pylori eradication therapy. | 2001 Feb |
|
| Cost-effectiveness of proton-pump inhibitors for maintenance therapy of erosive reflux esophagitis. | 2001 Jul 15 |
|
| Strategy for retreatment of therapeutic failure of eradication of Helicobacter pylori infection. | 2001 Jun |
|
| 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 |
|
| Laryngopharyngeal reflux symptoms improve before changes in physical findings. | 2001 Jun |
|
| Pharmacodynamic effects and kinetic disposition of rabeprazole in relation to CYP2C19 genotypes. | 2001 Jun |
|
| Efficacy and tolerability of antibiotics in patients undergoing H. pylori eradication. | 2001 Mar-Apr |
|
| Proton pump inhibitors and their drug interactions: an evidence-based approach. | 2001 May |
|
| [Modern means of anti-Helicobacter therapy]. | 2001 Oct |
|
| [Comparative antisecretory activity of famotidine, omeprazole, and rabeprazole (pariet) in ulcer disease based on daily pH-monitoring]. | 2001 Sep |
|
| Efficacy of triple therapy with rabeprazole for Helicobacter pylori infection and CYP2C19 genetic polymorphism. | 2001 Sep |
|
| 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 |
|
| [Cause and prevention of nocturnal gastric acid breakthrough]. | 2002 Feb |
|
| [Proton pump inhibitor-based quadruple therapy regimen for Helicobacter pylori infection]. | 2002 Feb |
|
| Acute fulminant hepatitis after treatment with rabeprazole and terbinafine: is rabeprazole the culprit? | 2002 Feb 11 |
|
| Gateways to clinical trials. | 2002 Jan-Feb |
|
| 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 |
|
| Randomized open trial for comparison of proton pump inhibitors in triple therapy for Helicobacter pylori infection in relation to CYP2C19 genotype. | 2002 Jul |
|
| The efficacy of lafutidine in improving preoperative gastric fluid property: a comparison with ranitidine and rabeprazole. | 2002 Jul |
|
| 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 |
|
| Onset of symptom relief with rabeprazole: a community-based, open-label assessment of patients with erosive oesophagitis. | 2002 Mar |
|
| Review article: rabeprazole-based therapy in Helicobacter pylori eradication. | 2002 Mar |
|
| Combination drug therapy for gastroesophageal reflux disease. | 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 |
|
| A new serum antibody test kit (E plate) for evaluation of Helicobacter pylori eradication. | 2002 Oct |
|
| Effects of rabeprazole, lansoprazole and omeprazole on intragastric pH in CYP2C19 extensive metabolizers. | 2002 Oct |
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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| Code System | Code | Type | Description | ||
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CHEMBL1219
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8769
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100000090030
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m9476
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3L36P16U4R
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SUB04192MIG
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3L36P16U4R
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14720269
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226868
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1598019
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GG-101
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DBSALT000552
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DTXSID3044205
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759270
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C80692
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117976-90-6
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ACTIVE MOIETY
SUBSTANCE RECORD
