Rabeprazole

Rabeprazole
Clinical data
Pronunciation /ˌræ.ˈbɛp.ræ.zɔːl/
Trade names AcipHex, others
AHFS/Drugs.com Monograph
MedlinePlus a699060
License data
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration		 by mouth
Drug class proton pump inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 52%
Metabolism mostly non-enzymatic,
partly Liver (CYP2C19)
Biological half-life 1 - 1.5 hours
Excretion 90% Kidney
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
PDB ligand
ECHA InfoCard 100.123.408
Chemical and physical data
Formula C18H21N3O3S
Molar mass 359.444 g/mol
3D model (JSmol)
Chirality Racemic mixture
  (verify)

Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. It was developed by Eisai Co. and is available worldwide under many brand names.

Medical uses

Bottle of rabeprazole 20 mg tablets.

Short-term treatment in healing and symptomatic relief of duodenal ulcers and erosive or gastroesophageal reflux disease (GERD); maintaining healing and reducing relapse rates of heartburn symptoms in patients with GERD; treatment of daytime and nighttime heartburn and other symptoms associated with GERD; long-term treatment of pathological hypersecretory conditions, including Zollinger-Ellison syndrome and in combination with amoxicillin and clarithromycin to eradicate Helicobacter pylori.

Contraindications

Side effects

Rabeprazole adverse reactions/side effects include:

Drug interactions

Rabeprazole decreases the concentration of ketoconazole in the plasma (in 33%), increases the concentration of digoxin (in 22%), and does not interact with liquid antacids. Rabeprazole is compatible with any medicine metabolized by the CYP450 (theophylline, warfarin, diazepam, phenytoin).

Overdosage

Studies in mice and rats indicated the symptoms of acute toxicity due to overdose included: hypoactivity, labored respiration, convulsion, diarrhea, tremor, and coma. A study in dogs indicated that a dose of 2000 mg/kg was not lethal.

Synthesis

Rabeprazole synthesis:[1] patents:[2]

Nitration of 2,3-dimethylpyridine N-oxide affords the nitro derivative. The newly introduced nitro group is then displaced by the alkoxide from 3-methoxypropanol to affords the corresponding ether (3). Treatment with acetic anhydride results in the Polonovski reaction. Saponification followed by treatment with thionyl chloride then chlorinates the primary alcohol (5). Reaction with benzimidazole-2-thiol (6) followed by oxidation of the resulting thioether to the sulfoxide then affords rabeprazole (8).

References

  1. ↑ Tagami, K.; Chiku, S.; Sohda, S. (1993). "Synthesis of 14C-labelled sodium pariprazole (E3810)". Journal of Labelled Compounds and Radiopharmaceuticals. 33 (9): 849. doi:10.1002/jlcr.2580330908.
  2. ↑ S. Souda et al., EP 268956; eidem, U.S. Patent 5,045,552 (1988, 1991 both to Eisai).
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