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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-10-17 09:25:06 UTC
Update Date2020-02-26 21:25:41 UTC
HMDB IDHMDB0005026
Secondary Accession Numbers
  • HMDB05026
Metabolite Identification
Common NameRabeprazole
DescriptionRabeprazole, also known as clofezone or pariet, belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety. Rabeprazole may also be used with antibiotics to get rid of bacteria that are associated with some ulcers. Rabeprazole is a drug which is used for the treatment of acid-reflux disorders (gerd), peptic ulcer disease, h. pylori eradication, and prevention of gastroinetestinal bleeds with nsaid use. Rabeprazole blocks the final step of gastric acid secretion. Rabeprazole is a strong basic compound (based on its pKa). Rabeprazole is a proton pump inhibitor sold (as its sodium salt) under the brand names Rabeprazole and Rabeprazole (distributed by Janssen-Cilag); Rabeprazole is a proton pump inhibitor sold (as its sodium salt) and it is used in the treatment of gastric ulcers and GERD (or heartburn). In humans, rabeprazole is involved in rabeprazole action pathway. It reduces symptoms and prevents injury to the esophagus or stomach in patients with gastroesophageal reflux disease (GERD) or ulcers. In gastric parietal cells, rabeprazole is protonated, accumulates, and is transformed to an active sulfenamide. In doing so, it inhibits the final transport of hydrogen ions (via exchange with potassium ions) into the gastric lumen. It is taken once a day along with a full glass of water (preferable 30 min before breakfast).
Structure
Data?1582752341
Synonyms
ValueSource
ClofezoneChEBI
EralocKegg
AciphexHMDB
HabeprazoleHMDB
ParietHMDB
ParietsHMDB
Rabeprazole sodiumHMDB
Sodium rabeprazoleHMDB
DexrabeprazoleHMDB
1H-Benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, sodium saltHMDB
2-((4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methylsulfinyl)-1H-benzimidazoleHMDB
Sodium, rabeprazoleHMDB
Chemical FormulaC18H21N3O3S
Average Molecular Weight359.443
Monoisotopic Molecular Weight359.130362243
IUPAC Name2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
Traditional Namerabeprazole
CAS Registry Number117976-89-3
SMILES
COCCCOC1=C(C)C(CS(=O)C2=NC3=CC=CC=C3N2)=NC=C1
InChI Identifier
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)
InChI KeyYREYEVIYCVEVJK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassSulfinylbenzimidazoles
Direct ParentSulfinylbenzimidazoles
Alternative Parents
Substituents
  • Sulfinylbenzimidazole
  • Alkyl aryl ether
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfoxide
  • Sulfinyl compound
  • Ether
  • Dialkyl ether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point101.7 - 103.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP2.04ALOGPS
logP2.09ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)4.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.1 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity98.07 m³·mol⁻¹ChemAxon
Polarizability39.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-009e-9843000000-7b2764dc90023b55c85cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-1938000000-25678fb8a17be5befc29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-c503bc067607aca1451eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2910000000-aa7552fe843abc4a67e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-2159000000-f97510bdc8045ab08ca6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-5792000000-af268bb77b35247f0f41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9800000000-6bea6647768de1869c4dSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01129
Phenol Explorer Compound IDNot Available
FooDB IDFDB023595
KNApSAcK IDNot Available
Chemspider ID4853
KEGG Compound IDC07864
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRabeprazole
METLIN IDNot Available
PubChem Compound5029
PDB IDNot Available
ChEBI ID8768
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSouda, Shigeru; Ueda, Norihiro; Miyazawa, Shuhei; Tagami, Katsuya; Nomoto, Seiichiro; Okita, Makoto; Shimomura, Naoyuki; Kaneko, Toshihiko; Fujimoto, Masatoshi; et al. Preparation of 2-[(4-alkoxypyrid-2-yl)methylthio]benzimidazoles, -benzothiazoles, and -benzoxazoles as ulcer inhibitors. Eur. Pat. Appl. (1988), 96 pp. CODEN: EPXXDW EP 268956 A2 19880601 CAN 110:23889 AN 1989:23889
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in sodium:potassium-exchanging ATPase activity
Specific function:
Not Available
Gene Name:
ATP4B
Uniprot ID:
P51164
Molecular weight:
33367.0
General function:
Involved in ATP binding
Specific function:
Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach.
Gene Name:
ATP4A
Uniprot ID:
P20648
Molecular weight:
114117.74