An active metabolite of rabeprazole
Related Products
Parent Compound(s)
14939Rabeprazole (sodium salt)
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Rabeprazole Sulfide

Item No. 36276

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]thio]-1H-benzimidazole
CAS Number
117977-21-6
Synonyms
  • Rabeprazole Thioether
Molecular Formula
C18H21N3O2S
Formula Weight
343.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/ml
SMILES
COCCCOC1=C(C)C(CSC2=NC3=CC=CC=C3N2)=NC=C1
InChi Code
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)
InChi Key
BSXAHDOWMOSVAP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    250 mg

    $32

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    500 mg

    $61

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    1 g

    $112

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    5 g

    $465

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    Cayman Chemical
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    Product Description

    Rabeprazole sulfide is an active metabolite of the proton pump inhibitor rabeprazole (Item No. 14939).1 It inhibits the motility of H. pylori (IC50 = 0.25 µg/ml).2 Rabeprazole sulfide is cytotoxic to HepG2 liver and PANC-1 pancreatic cancer cells (IC50s = 0.08 and 0.17 µM, respectively).3 It is also a potential impurity in commercial preparations of rabeprazole and an acid and neutral hydrolytic degradation product of rabeprazole.4,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cao, N., Liu, L., Hao, Y.-B., et al. Simultaneous determination of rabeprazole enantiomers and their four metabolites after intravenous administration in beagle dogs by a stereoselective HPLC-MS/MS method and its application in pharmacokinetic studies. Anal. Methods 8, 1405 (2016).

    2. Tsutsui, N., Taneike, I., Ohara, T., et al. A novel action of the proton pump inhibitor rabeprazole and its thioether derivative against the motility of Helicobacter pylori. Antimicrob. Agents Chemother. 44(11), 3069-3073 (2000).

    3. Bhandi, M.M., Borkar, R.M., Shankar, G., et al. Identification and characterization of stressed degradation products of rabeprazole using LC-ESI/MS/MS and 1H-NMR experiments: In vitro toxicity evaluation of major degradation products. RSC Adv. 6, 10719 (2016).

    4. Reddy, G.M., Bhaskar, B.V., Reddy, P.P., et al. Identification and characterization of potential impurities of rabeprazole sodium. J. Pharm. Biomed. Anal. 43(4), 1262-1269 (2007).