Rabeprazole

Rabeprazole
Clinical data
Pronunciation	/rəˈbɛprəˌzɔːl/
Trade names	Aciphex, Pariet, Rafron, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699060
License data	US DailyMed: Rabeprazole; US FDA: Rabeprazole;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
Drug class	Proton pump inhibitor
ATC code	A02BC04 (WHO) A02BC54 (WHO) A02BD12 (WHO) A02BD13 (WHO);
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	52%
Protein binding	96.3%
Metabolism	CYP2C19 and CYP3A4 in the liver
Metabolites	thioether carboyxlic acid metabolite, thioether glucuronide metabolite, sulfone metabolite
Elimination half-life	~1 hour
Excretion	90% via kidney as metabolites
Identifiers
	IUPAC name (RS)-2-([4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole;
CAS Number	117976-89-3 ;
PubChem CID	5029;
IUPHAR/BPS	7290;
DrugBank	DB01129 ;
ChemSpider	4853 ;
UNII	32828355LL;
KEGG	D08463 ; C07864 ;
ChEBI	CHEBI:8768 ;
ChEMBL	ChEMBL1219 ;
PDB ligand	RZX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3044122 ;
ECHA InfoCard	100.123.408
Chemical and physical data
Formula	C18H21N3O3S
Molar mass	359.44 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCCCOC;
	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) ; Key:YREYEVIYCVEVJK-UHFFFAOYSA-N ;
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Rabeprazole, sold under the brand name Aciphex, among others, is a medication that decreases stomach acid. It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and excess stomach acid production such as in Zollinger–Ellison syndrome. It may also be used in combination with other medications to treat Helicobacter pylori. Effectiveness is similar to other proton pump inhibitors (PPIs). It is taken by mouth.

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

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