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117976-89-3 molecular structure
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2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole

ChemBase ID: 1000
Molecular Formular: C18H21N3O3S
Molecular Mass: 359.44264
Monoisotopic Mass: 359.13036255
SMILES and InChIs

SMILES:
S(=O)(Cc1nccc(OCCCOC)c1C)c1[nH]c2c(n1)cccc2
Canonical SMILES:
COCCCOc1ccnc(c1C)CS(=O)c1nc2c([nH]1)cccc2
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)
InChIKey:
YREYEVIYCVEVJK-UHFFFAOYSA-N

Cite this record

CBID:1000 http://www.chembase.cn/molecule-1000.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
IUPAC Traditional name
rabeprazole
2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
Brand Name
AcipHex
Pariet
Synonyms
2-(((4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole
Irsogladine Maleate
Rebeprazole sodium
rabeprazole sodium
Rabeprazole
CAS Number
117976-89-3
MDL Number
MFCD00868879
PubChem SID
160964463
46506366
PubChem CID
5029

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Bide Pharmatech
BD16918 Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.346711  H Acceptors
H Donor LogD (pH = 5.5) 2.0682993 
LogD (pH = 7.4) 2.0861723  Log P 2.0907433 
Molar Refractivity 98.0668 cm3 Polarizability 39.284637 Å3
Polar Surface Area 77.1 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.04  LOG S -3.03 
Solubility (Water) 3.36e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Hydrophobicity(logP)
0.6 expand Show data source
Purity
95+% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01129 external link
Item Information
Drug Groups approved; investigational
Description Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. It is a prodrug - in the acid environment of the parietal cells it turns into active sulphenamide form. Rabeprazole inhibits the H+, K+ATPase of the coating gastric cells and dose-dependent oppresses basal and stimulated gastric acid secretion.
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacology Rabeprazole prevents the production of acid in the stomach. It reduces symptoms and prevents injury to the esophagus or stomach in patients with gastroesophageal reflux disease (GERD) or ulcers. Rabeprazole is also useful in conditions that produce too much stomach acid such as Zollinger-Ellison syndrome. Rabeprazole may also be used with antibiotics to get rid of bacteria that are associated with some ulcers. Rabeprazole is a selective and irreversible proton pump inhibitor, suppresses gastric acid secretion by specific inhibition of the H+, K+ -ATPase, which is found at the secretory surface of parietal cells. In doing so, it inhibits the final transport of hydrogen ions (via exchange with potassium ions) into the gastric lumen.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Absolute bioavailability is approximately 52%.
Half Life 1-2 hours (in plasma)
Protein Binding 96.3% (bound to human plasma proteins)
Elimination Following a single 20 mg oral dose of 14C-labeled rabeprazole, approximately 90% of the drug was eliminated in the urine, primarily as thioether carboxylic acid; its glucuronide, and mercapturic acid metabolites.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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