Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H20N3O3S.Na.H2O |
| Molecular Weight | 399.44 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].COCCCOC1=CC=NC(C[S+]([O-])C2=NC3=C([N-]2)C=CC=C3)=C1C
InChI
InChIKey=HKZVUFAIQCTTTD-UHFFFAOYSA-N
InChI=1S/C18H20N3O3S.Na.H2O/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;;1H2/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 |
|
| Efficacy of Helicobacter pylori eradication therapies: a single centre observational study. | 2001 |
|
| [A new blocker of proton pump pariet: pharmacological properties and effectiveness of clinical application]. | 2001 |
|
| 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 |
|
| Duodenal mucosa-associated lymphoid tissue lymphoma treated by eradication of Helicobacter pylori: report of 2 cases including EUS findings. | 2001 Dec |
|
| 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 |
|
| Acute fulminant hepatitis after treatment with rabeprazole and terbinafine. | 2001 Jul 9 |
|
| Training in the step-down inhibitory avoidance task time-dependently increases cAMP-dependent protein kinase activity in the entorhinal cortex. | 2001 Jun |
|
| CYP2C19 genotype and pharmacokinetics of three proton pump inhibitors in healthy subjects. | 2001 Jun |
|
| Pharmacodynamic effects and kinetic disposition of rabeprazole in relation to CYP2C19 genotypes. | 2001 Jun |
|
| Efficacy of rabeprazole once daily for acid-related disorders. | 2001 Mar |
|
| Efficacy and tolerability of antibiotics in patients undergoing H. pylori eradication. | 2001 Mar-Apr |
|
| [Safety profile of pariet clinical use (a literature review)]. | 2001 May |
|
| New-generation proton pump inhibitors: overcoming the limitations of early-generation agents. | 2001 May |
|
| 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 |
|
| Proton pump inhibition. An effective, safe approach to GERD management. | 2001 Oct |
|
| [Modern means of anti-Helicobacter therapy]. | 2001 Oct |
|
| Optimizing acid-suppression therapy. | 2001 Oct |
|
| Comparison of the kinetic disposition of and serum gastrin change by lansoprazole versus rabeprazole during an 8-day dosing scheme in relation to CYP2C19 polymorphism. | 2001 Sep |
|
| [Pariet in eradication therapy plans]. | 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 |
|
| [Regeneration of the gastric epitheliocytes during treatment of duodenal ulcer with pariet]. | 2002 Apr |
|
| Levofloxacin based regimens for the eradication of Helicobacter pylori. | 2002 Dec |
|
| Treatment and management of Helicobacter pylori infection. | 2002 Dec |
|
| [Dual therapy for Helicobacter pylori resistance to anti microbial agents]. | 2002 Feb |
|
| [Pharma-clinics medication of the month. Rabeprazole (Pariet)]. | 2002 Jan |
|
| Treatment with a proton pump inhibitor promotes corpus gastritis in patients with Helicobacter pylori-infected antrum-predominant gastritis. | 2002 Jan |
|
| Drug combinations with amoxycillin reduce selection of clarithromycin resistance during Helicobacter pylori eradication therapy. | 2002 Jan |
|
| [Evaluation of efficacy, safety and tolerability rabeprazole in treatment of acid-peptic diseases ]. | 2002 Jan-Mar |
|
| Rabeprazole. | 2002 Jan-Mar |
|
| Effects of rabeprazole, 20 mg, or esomeprazole, 20 mg, on 24-h intragastric pH and serum gastrin in healthy subjects. | 2002 Jul |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Onset of symptom relief with rabeprazole: a community-based, open-label assessment of patients with erosive oesophagitis. | 2002 Mar |
|
| Primary hyperparathyroidism with duodenal ulcer and H. pylori infection. | 2002 May |
|
| Rabeprazole improves health-related quality of life in patients with erosive gastroesophageal reflux disease. | 2002 Nov |
|
| Eradication rates of clarithromycin-resistant Helicobacter pylori using either rabeprazole or lansoprazole plus amoxicillin and clarithromycin. | 2002 Nov |
|
| Effects of rabeprazole, lansoprazole and omeprazole on intragastric pH in CYP2C19 extensive metabolizers. | 2002 Oct |
|
| Gateways to Clinical Trials. | 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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100000175197
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5XH0X84AHJ
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71587910
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
