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QuickView for rabeprazole (compound)

Summary
General Info

PubChem

PubChem Compound 10786084

PubChem Compound 10786084

Name:	rabeprazole
PubChem Compound ID:	10786084
Molecular formula:	C₁₈H₂₀N₃NaO₃S
Molecular weight:	381.426 g/mol

DrugBank

Identification

Name:	rabeprazole
Name (isomeric):	DB01129
Drug Type:	small molecule
Synonyms:	Rebeprazole sodium; rabeprazole sodium; Irsogladine Maleate
Brand:	AcipHex, Pariet
Category:	Anti-Ulcer Agents, Enzyme Inhibitors
CAS number:	117976-89-3

Pharmacology

Indication:	For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacology:	Rabeprazole prevents the production of acid in the stomach. It reduces symptoms and prevents injury to the esophagus or stomach in patients with gastroesophageal reflux disease (GERD) or ulcers. Rabeprazole is also useful in conditions that produce too much stomach acid such as Zollinger-Ellison syndrome. Rabeprazole may also be used with antibioti... show more » Rabeprazole prevents the production of acid in the stomach. It reduces symptoms and prevents injury to the esophagus or stomach in patients with gastroesophageal reflux disease (GERD) or ulcers. Rabeprazole is also useful in conditions that produce too much stomach acid such as Zollinger-Ellison syndrome. Rabeprazole may also be used with antibiotics to get rid of bacteria that are associated with some ulcers. Rabeprazole is a selective and irreversible proton pump inhibitor, suppresses gastric acid secretion by specific inhibition of the H⁺, K⁺ -ATPase, which is found at the secretory surface of parietal cells. In doing so, it inhibits the final transport of hydrogen ions (via exchange with potassium ions) into the gastric lumen. show less «
Mechanism of Action:	Rabeprazole belongs to a class of antisecretory compounds (substituted benzimidazole proton-pump inhibitors) that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but suppress gastric acid secretion by inhibiting the gastric H⁺/K⁺ATPase (hydrogen-potassium adenosine triphosphatase) at the secretor... show more » Rabeprazole belongs to a class of antisecretory compounds (substituted benzimidazole proton-pump inhibitors) that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but suppress gastric acid secretion by inhibiting the gastric H⁺/K⁺ATPase (hydrogen-potassium adenosine triphosphatase) at the secretory surface of the gastric parietal cell. Because this enzyme is regarded as the acid (proton) pump within the parietal cell, rabeprazole has been characterized as a gastric proton-pump inhibitor. Rabeprazole blocks the final step of gastric acid secretion. In gastric parietal cells, rabeprazole is protonated, accumulates, and is transformed to an active sulfenamide. When studied in vitro, rabeprazole is chemically activated at pH 1.2 with a half-life of 78 seconds. show less «
Absorption:	Absolute bioavailability is approximately 52%.
Protein binding:	96.3% (bound to human plasma proteins)
Biotransformation:	Hepatic
Route of elimination:	Following a single 20 mg oral dose of 14C-labeled rabeprazole, approximately 90% of the drug was eliminated in the urine, primarily as thioether carboxylic acid; its glucuronide, and mercapturic acid metabolites.
Half Life:	1-2 hours (in plasma)
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals.

Take without regard to meals. Food may slow absorption rate but extent of absorption is not affected.

Drug interaction:

Tretinoin	The moderate CYP2C8 inhibitor, Rabaprazole, may decrease the metabolism and clearance of oral Tretinoin. Monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Rabaprazole is initiated, discontinued to dose changed.
Indinavir	Omeprazole decreases the absorption of indinavir
Cefditoren	Proton pump inhibitors such as rabeprazole may decrease the serum concentration of cefditoren. If possible, avoid use of cefditoren with proton pump inhibitors (PPIs). Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of PPIs can not be avoided.
Itraconazole	The proton pump inhibitor, rabeprazole, may decrease the absorption of itraconazole.
Digoxin	Rabeprazole increases the effect of digoxin

Targets

Potassium-transporting ATPase alpha chain 1

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2C19

Cytochrome P450 1A1

Cytochrome P450 1A2

Cytochrome P450 2C9

Cytochrome P450 2D6

Transporters

ATP-binding cassette sub-family G member 2