Rabeprazole

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 O=S(c2nc1ccccc1n2)Cc3nccc(OCCCOC)c3C
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 (/ˈæsɨfɛks/, referring to pH) in the US, Pariet in Europe, Brazil, Canada, Japan, Russia and Australia, and Razo, Parit and Orpro in India.

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.
• abdominal pains
• anxiety
• arthralgia
• asthenia
• constipation
• diarrhea
• dry mouth
• erythema
• granulocytopenia
• headache
• increased or decreased appetite
• insomnia
• leukocytopenia
• meteorism
• muscle or bone pain
• myalgia
• nausea
• skin eruption
• thrombocytopenia
• vertigo
• vomiting

Antacid preparations such as rabeprazole by suppressing acid mediated break down of proteins, leads to an elevated risk of developing food or drug allergies. This happens due to undigested proteins then passing into the gastrointestinal tract where sensitisation occurs. It is unclear whether this risk occurs with only long-term use or with short-term use as well.

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 "CYRA" (Systopic Labs Pvt Ltd), "Elpizole" (Orchid Chemicals & Pharmaceuticals), "Elpizole -20" (Orchid Chemicals & Pharmaceuticals), Rablet (Lupin), Acigard (3D), AcipHex, Rabeloc, Pariet, Rabider (Duta Formulations) is supplied in:

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

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

References

• 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

• AcipHex official product site
• Rabeprazole bound to proteins in the PDB