Structure via PubChem · Public domain (PubChem)
(RS)-rabeprazole
Sign in to saveAlso known as E-3810
Rabeprazole, sold under the brand name Aciphex, among others, is a medication that decreases stomach acid. It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and excess stomach acid production such as in Zollinger–Ellison syndrome. It may also be used in combination with other medications to treat Helicobacter pylori. Effectiveness is similar to other proton pump inhibitors (PPIs). It is taken by mouth.
Key facts
- Drug.ATC_suffix
- BC04
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.S
- 1
- Drug.bioavailability
- 52%
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462080585
- Drug.image
- Rabeprazole enantiomers labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.image2
- Rabeprazole enantiomers ball-and-stick models from xtal 2011.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 300
- Drug.chirality
- Racemic mixture
- Drug.tradename
- Aciphex, Pariet, Rafron, others
- Drug.MedlinePlus
- a699060
- Drug.DailyMedID
- Rabeprazole
- Drug.licence_US
- Rabeprazole
via Wikipedia infobox
Chemical data
- Formula
- C18H21N3O3S
- Molecular weight
- 359.4 g/mol
- IUPAC name
- 2-[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methylsulfinyl]-1H-benzimidazole
- SMILES
- CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCCCOC
- InChIKey
- YREYEVIYCVEVJK-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 96.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
23 papersvia PubMed
Wikidata facts
- Mass
- 359.13
Show 6 more facts
- Commons category
- Rabeprazole
- chemical formula
- C₁₈H₂₁N₃O₃S
- canonical SMILES
- CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCCCOC
- World Health Organisation international non-proprietary name
- rabeprazole
- defined daily dose
- 20
- stylized name
- RABEprazole
via Wikidata · CC0
~34 min read
Article
39 sectionsContents
- Medical uses
- Available forms
- Specific populations
- Pediatrics
- Pregnancy
- Lactation
- Geriatrics
- Japanese ancestry
- Kidney or liver problems
- Contraindications
- Hypersensitivity
- Syndrome
- Cross-reactivity
- Rilpivirine
- Adverse effects
- Osteoporosis and fractures
- Infection risk
- Nephrotoxicity
- Muscle-related adverse events
- Overdose
- Interactions
- Drug-drug interactions
- Food-drug interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Pharmacogenetics
- Chemistry
- Synthesis
- Comparative chemistry
- Physiochemical properties
- History
- Development
- Society and culture
- Legal status
- Brand names
- Research
- References
- External links
Rabeprazole, sold under the brand name Aciphex, among others, is a medication that decreases stomach acid. It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and excess stomach acid production such as in Zollinger–Ellison syndrome. It may also be used in combination with other medications to treat Helicobacter pylori. Effectiveness is similar to other proton pump inhibitors (PPIs). It is taken by mouth.
Common side effects include constipation, feeling weak, and throat inflammation. Serious side effects may include osteoporosis, low blood magnesium, Clostridioides difficile infection, and pneumonia. Use in pregnancy and breastfeeding is of unclear safety. It works by blocking H+/K+-ATPase in the parietal cells of the stomach.