Rabeprazole

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Rabeprazole
Rabeprazole.png
Rabeprazole3d.png
Clinical data
AHFS/Drugs.com Monograph
MedlinePlus a699060
License data
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration
Oral
ATC code A02BC04 (WHO)
Legal status
Legal status
Pharmacokinetic data
Bioavailability 52%
Metabolism mostly non-enzymatic,
partly hepatic (CYP2C19)
Biological half-life 1 - 1.5 hours
Excretion 90% renal
Identifiers
CAS Number 117976-89-3 YesY
PubChem (CID) 5029
IUPHAR/BPS 7290
DrugBank DB01129 YesY
ChemSpider 4853 YesY
UNII 32828355LL YesY
ChEBI CHEBI:8768 YesY
ChEMBL CHEMBL1219 YesY
PDB ligand ID RZX (PDBe, RCSB PDB)
ECHA InfoCard 100.123.408
Chemical and physical data
Formula C18H21N3O3S
Molar mass 359.444 g/mol
3D model (Jmol) Interactive image
Chirality Racemic mixture
  (verify)

Rabeprazole /ˌræ.ˈbɛp.ræ.zɔːl/ 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.

Indications and usage[edit]

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.

  • Gastric ulcer (GU)
  • Peptic ulcer disease (PUD)
  • Maintenance of healing of erosive or ulcerative GERD
  • Healing of erosive and ulcerative GERD
  • Healing of duodenal ulcers.
  • Treatment of symptomatic GERD
  • Treatment of pathological hypersecretory conditions (Zollinger-Ellison syndrome)
  • Helicobacter pylori eradication to reduce risk of duodenal ulcer recurrence

Contraindications[edit]

  • hypersensitivity to rabeprazole, substituted benzimidazoles or any of components of its pharmaceutical forms.
  • lactation: Thomson Lactation Ratings: Infant risk cannot be ruled out.

Restriction of usage[edit]

Bottle of rabeprazole 20 mg tablets.
  • acute liver failure
  • pediatric use in patients under 18 years of age (there are insufficient data about safety and efficiency of rabeprazole in this group of patients)

Side effects[edit]

Rabeprazole adverse reactions/side effects include[citation needed]:

Drug interactions[edit]

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[edit]

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[edit]

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[edit]

  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).
  • Morii M, Takata H, Fujisaki H, Takeguchi N., The potency of substituted benzimidazoles such as E3810, omeprazole, Ro 18-5364 to inhibit gastric H+, K(+)-ATPase is correlatedwith the rate of acid-activation of the inhibitor, Biochem. Pharmacol. 1990 Feb 15;39(4):661-7.
  • Prakash A, Faulds D., Rabeprazole, Drugs. 1998 Feb;55(2):261-7; discussion 268.

External links[edit]