2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfanyl)-1H-1,3-benzodiazole

• ChemBase ID: 69887
• Molecular Formular: C18H21N3O2S
• Molecular Mass: 343.44324
• Monoisotopic Mass: 343.13544793
• SMILES: c1(nc2c([nH]1)cccc2)SCc1c(c(ccn1)OCCCOC)C
• Canonical SMILES: COCCCOc1ccnc(c1C)CSc1nc2c([nH]1)cccc2
• InChI: InChI=1S/C18H21N3O2S/c1-13-16(19-9-8-17(13)23-11-5-10-22-2)12-24-18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)
• InChIKey: BSXAHDOWMOSVAP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfanyl)-1H-1,3-benzodiazole
• IUPAC Traditional name: 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfanyl)-1H-1,3-benzodiazole
• Synonyms: 2-[[[3-Methyl-4-(3-methoxypropoxy)-2-pyridyl]methyl]thio]-1H-benzimidazole; 2-{[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl]-methythio}-1H-benzimidazole; H 295/43; Rabeprazole Thioether; Rabeprazole Sulfide; 2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole

Database IDs

• CAS Number: 117977-21-6
• MDL Number: MFCD08063845
• PubChem SID: 162035612
• PubChem CID: 9949996

CALCULATED PROPERTIES

• Acid pKa: 10.421231
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5183535
• LogD (pH = 7.4): 3.1937652
• Log P: 3.2176442
• Molar Refractivity: 96.6951 cm^3
• Polarizability: 38.75045 Å^3
• Polar Surface Area: 60.03 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 109-110°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - R070510

A metabolite of Rabeprazole (R070500).

REFERENCES

• Yoshida, T., et al.: Biotech. Lett., 23, 1217 (2001)
• Miura, M., et al.: Eur. J. Clin. Pharmacol., 62, 113 (2001)
• Sheridan, R.P., et al.: J. Med. Chem., 50, 3173 (2001)
• Ren, S., et al.: Arc. Pharm. Res., 31, 406 (2001)