Rabeprazole

Rabeprazole
Clinical data
Pronunciation/rəˈbɛprəˌzɔːl/
Trade namesAciphex, Pariet, Rafron, others
AHFS/Drugs.comMonograph
MedlinePlusa699060
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classProton pump inhibitor[2]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability52%[2]
Protein binding96.3%[3]
MetabolismCYP2C19 and CYP3A4 in the liver[2]
Metabolitesthioether carboyxlic acid metabolite, thioether glucuronide metabolite, sulfone metabolite[3]
Elimination half-life~1 hour[2]
Excretion90% via kidney as metabolites[4][5]
Identifiers
  • (RS)-2-([4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.123.408 Edit this at Wikidata
Chemical and physical data
FormulaC18H21N3O3S
Molar mass359.44 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture[2]
  • CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCCCOC
  • 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) checkY
  • Key:YREYEVIYCVEVJK-UHFFFAOYSA-N checkY
  (verify)

Rabeprazole, sold under the brand name Aciphex, among others, is a medication that decreases stomach acid.[6] It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and excess stomach acid production such as in Zollinger–Ellison syndrome.[6] It may also be used in combination with other medications to treat Helicobacter pylori.[7] Effectiveness is similar to other proton pump inhibitors (PPIs).[8] It is taken by mouth.[6]

Common side effects include constipation, feeling weak, and throat inflammation.[6] Serious side effects may include osteoporosis, low blood magnesium, Clostridioides difficile infection, and pneumonia.[6] Use in pregnancy and breastfeeding is of unclear safety.[1] It works by blocking H+/K+-ATPase in the parietal cells of the stomach.[6]

Rabeprazole was patented in 1986, and approved for medical use in 1997.[9] It is available as a generic medication.[7] In 2017, it was the 288th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[10]

  1. ^ a b c "Rabeprazole Use During Pregnancy". Drugs.com. 25 June 2018. Retrieved 10 January 2020.
  2. ^ a b c d e Cite error: The named reference Marelli Review 2012 was invoked but never defined (see the help page).
  3. ^ a b Langtry HD, Markham A (October 1999). "Rabeprazole: a review of its use in acid-related gastrointestinal disorders". Drugs. 58 (4): 725–742. doi:10.2165/00003495-199958040-00014. PMID 10551440. S2CID 195691083.
  4. ^ "Rabeprazole". PubChem. NCBI. Retrieved 10 January 2020.
  5. ^ "Rabeprazole". PubChem. U.S. National Library of Medicine. Retrieved 10 January 2020.
  6. ^ a b c d e f "Rabeprazole Sodium Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  7. ^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 82. ISBN 9780857113382.
  8. ^ "[99] Comparative effectiveness of proton pump inhibitors". Therapeutics Initiative. 28 June 2016. Retrieved 14 July 2016.
  9. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
  10. ^ "Rabeprazole - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.