Rabeprazole

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Rabeprazole


Systematic (IUPAC) name
(RS)-2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
Clinical data
Trade names	Aciphex
AHFS/Drugs.com	monograph
MedlinePlus	a699060
Licence data	US FDA:link
Pregnancy cat.	B (US)
Legal status	POM (UK) ℞-only (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	52%
Metabolism	mostly non-enzymatic, partly hepatic (CYP2C19)
Half-life	1 - 1.5 hours
Excretion	90% renal
Identifiers
CAS number	117976-89-3^Y
ATC code	A02BC04
PubChem	CID 5029
DrugBank	DB01129
ChemSpider	4853^Y
UNII	32828355LL^Y
ChEBI	CHEBI:8768^Y
ChEMBL	CHEMBL1219^Y
Chemical data
Formula	C₁₈H₂₁N₃O₃S
Mol. mass	359.444 g/mol
SMILES	eMolecules & PubChem
InChI 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)^Y Key:YREYEVIYCVEVJK-UHFFFAOYSA-N^Y
Y (what is this?) (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 marketed by Janssen-Cilag as rabeprazole sodium under the brand names AcipHex (English pronunciation: /ˈæsɨfɛks/, referring to pH) in the US and Pariet in Britain, Italy, Greece, Australia, Brazil, Canada, Japan, and Russia.

Indications and usage

Short-term treatment in healing and symptomatic relief of duodenal ulcers and erosive or ulcerative 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.
pregnancy: FDA Pregnancy Ratings: B
lactation: Thomson Lactation Ratings: Infant risk cannot be ruled out.

Restriction of usage

Bottle of rabeprazole 20 mg tablets.

acute hepatic 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]}:

In clinical trials the most common side effect assessed as possibly or probably related to AcipHex was headache in 2.4% of patients vs 1.6% taking placebo.
diarrhea
vomiting
nausea
abdominal pains
constipation
meteorism
dry mouth
increased or decreased appetite
asthenia
headache
anxiety
sleeplessness
vertigo
thrombocytopenia
granulocytopenia
leukocytopenia
skin eruption
erythema
myalgia
arthralgia
muscle or bone pain

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 2000mg/kg was not lethal.

Formulations and brand names

Rabeprazole as "Elpizole" (Orchid Chemicals & Pharmaceuticals), "Elpizole -20" (Orchid Chemicals & Pharmaceuticals) Rablet (Lupin), AcipHex, Rabeloc, Pariet is supplied in:

Tablet, enteric-coated; 10 mg
Tablet, enteric-coated; 20 mg

Rabeprazole is sold under the brand names Rabium, Esoon, Rabemac, Rabiloz, Razo and Rablet in India, and Zechin in Pakistan.

References

This article includes a list of references, related reading or external links, but its sources remain unclear because it lacks inline citations. Please improve this article by introducing more precise citations. (May 2012)

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.