Rabeprazole

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Rabeprazole
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Systematic (IUPAC) name
(RS)-2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a699060
Licence data US FDA:Finix&SearchType=BasicSearch link
Pregnancy
category
  • US: B (No risk in non-human studies)
Legal status
Routes of
administration		 Oral
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
ATC code A02BC04 (WHO)
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)
Chemical data
Formula C18H21N3O3S
Molecular mass 359.444 g/mol
  • O=S(c2nc1ccccc1n2)Cc3nccc(OCCCOC)c3C
  • InChI=1S/C18H21N3O3S/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,(H,20,21) YesY
  • Key:YREYEVIYCVEVJK-UHFFFAOYSA-N YesY
  (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

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

  • 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

File:Aciphex-sample-bottle.jpg
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

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

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

File:Rabeprazole synthesis.svg
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 Ac2O results in the Polonovski reaction. Saponification followed by treatment with SOCl2 then chlorinates the primary alcohol (5). Condensation with benzimidazole-2-thiol (6) followed by oxidation of the resulting thioether to the sulfoxide then affords rabeprazole (8).

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ S. Souda et al., EP 268956 ; eidem, U.S. Patent 5,045,552 (1988, 1991 both to Eisai).

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  • 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

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