Rabeprazole sulfide | CAS#117977-21-6 | proton pump inhibitor

MedKoo Cat#: 461117 | Name: Rabeprazole sulfide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rabeprazole sulfide is an active metabolite of rabeprazole, a proton pump inhibitor.

Chemical Structure

Rabeprazole sulfide

CAS#117977-21-6

Theoretical Analysis

MedKoo Cat#: 461117

Name: Rabeprazole sulfide

CAS#: 117977-21-6

Chemical Formula: C18H21N3O2S

Exact Mass: 343.1354

Molecular Weight: 343.45

Elemental Analysis: C, 62.95; H, 6.16; N, 12.24; O, 9.32; S, 9.33

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 1,360.00

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Synonym

Rabeprazole thioether; Rabeprazole impurity E; Rabeprazole sulfide

IUPAC/Chemical Name

2-(((4-(3-methoxypropoxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole

InChi Key

BSXAHDOWMOSVAP-UHFFFAOYSA-N

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)

SMILES Code

Cc1c(CSc([nH]2)nc3c2cccc3)nccc1OCCCOC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rabeprazole is a proton pump inhibitor (PPI) that irreversibly inactivates gastric H+/K+-ATPase. Rabeprazole induces apoptosis and acts as an uridine nucleoside ribohydrolase (UNH) inhibitor with an IC50 of 0.3 μM.

In vitro activity:

This study found that rabeprazole can attenuate the cell viability of human gastric cancer cells by inactivating the ERK1/2 signaling pathway. These results demonstrate that since rabeprazole inhibits the viability of gastric cancer cells in vitro, it may serve as a novel antineoplastic agent. Reference: Oncol Lett. 2014 Oct;8(4):1739-1744. https://pubmed.ncbi.nlm.nih.gov/25202402/

In vivo activity:

This study found that the calculated cumulative urinary recovery just reached 1.272‰ of dose within 24h post-dose for rabeprazole sulfide after intravenous infusion administration, indicating that rabeprazole sulfide undergoes substantial non-renal elimination in healthy Chinese volunteers. Reference: J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Apr 15;988:75-80. https://pubmed.ncbi.nlm.nih.gov/25755073/

	Solvent	mg/mL	mM
Solubility
	DMSO	3.5	10.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 343.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Gu M, Zhang Y, Zhou X, Ma H, Yao H, Ji F. Rabeprazole exhibits antiproliferative effects on human gastric cancer cell lines. Oncol Lett. 2014 Oct;8(4):1739-1744. doi: 10.3892/ol.2014.2354. Epub 2014 Jul 16. PMID: 25202402; PMCID: PMC4156221. 2. Tamaro I, Genazzani A, Canonico P, Grosa G. Lack of in vitro interactions using human liver microsomes between rabeprazole and anticancer drugs. Eur J Drug Metab Pharmacokinet. 2009 Jan-Mar;34(1):19-26. doi: 10.1007/BF03191379. PMID: 19462924. 3. Chen SQ, Hu BF, Yang YR, He Y, Yue L, Guo D, Wu TN, Feng XW, Li Q, Zhang W, Wen JG. The protective effect of rabeprazole on cisplatin-induced apoptosis and necroptosis of renal proximal tubular cells. Biochem Biophys Res Commun. 2022 Jul 5;612:91-98. doi: 10.1016/j.bbrc.2022.04.107. Epub 2022 Apr 25. PMID: 35512462. 4. Lu C, Jia Y, Song Y, Li X, Sun Y, Zhao J, Wang S, Shi L, Wen A, Ding L. Application of a liquid chromatographic/tandem mass spectrometric method to a urinary excretion study of rabeprazole and two of its metabolites in healthy human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Apr 15;988:75-80. doi: 10.1016/j.jchromb.2015.01.023. Epub 2015 Jan 23. PMID: 25755073.

In vitro protocol:

In vivo protocol:

1. Chen SQ, Hu BF, Yang YR, He Y, Yue L, Guo D, Wu TN, Feng XW, Li Q, Zhang W, Wen JG. The protective effect of rabeprazole on cisplatin-induced apoptosis and necroptosis of renal proximal tubular cells. Biochem Biophys Res Commun. 2022 Jul 5;612:91-98. doi: 10.1016/j.bbrc.2022.04.107. Epub 2022 Apr 25. PMID: 35512462. 2. Lu C, Jia Y, Song Y, Li X, Sun Y, Zhao J, Wang S, Shi L, Wen A, Ding L. Application of a liquid chromatographic/tandem mass spectrometric method to a urinary excretion study of rabeprazole and two of its metabolites in healthy human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Apr 15;988:75-80. doi: 10.1016/j.jchromb.2015.01.023. Epub 2015 Jan 23. PMID: 25755073.

Su B, Xu F, Zhong J, Xu X, Lin J. Rational design on loop regions for precisely regulating flexibility of catalytic center to mitigate overoxidation of prazole sulfides by Baeyer-Villiger monooxygenase. Bioorg Chem. 2024 Oct;151:107718. doi: 10.1016/j.bioorg.2024.107718. Epub 2024 Aug 12. PMID: 39142195. Cao NT, Cha GS, Kim JH, Lee Y, Yun CH, Nguyen NA. Production of an O-desmethylated product, a major human metabolite, of rabeprazole sulfide by bacterial P450 enzymes. Enzyme Microb Technol. 2023 Dec;171:110328. doi: 10.1016/j.enzmictec.2023.110328. Epub 2023 Sep 20. PMID: 37751627. Patel H, Desai N, Patel P, Modi N, Soni K, Patel JR, Mistry GN, Patel JD, Chawla M, Srinivas NR. Pharmacokinetic evaluation of differential drug release formulations of rabeprazole in dogs. Drug Dev Ind Pharm. 2019 Sep;45(9):1459-1467. doi: 10.1080/03639045.2019.1628249. Epub 2019 Jun 20. PMID: 31216902. 1: Lu C, Jia Y, Song Y, Li X, Sun Y, Zhao J, Wang S, Shi L, Wen A, Ding L. Application of a liquid chromatographic/tandem mass spectrometric method to a urinary excretion study of rabeprazole and two of its metabolites in healthy human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Apr 15;988:75-80. doi: 10.1016/j.jchromb.2015.01.023. Epub 2015 Jan 23. PubMed PMID: 25755073. 2: Simpemba E, Liu R, Sun C, Agbokponto JE, Ding L. Simultaneous determination of rabeprazole and its two active metabolites in human urine by liquid chromatography with tandem mass spectrometry and its application in a urinary excretion study. J Sep Sci. 2014 Aug;37(15):1951-6. doi: 10.1002/jssc.201400162. Epub 2014 Jun 30. PubMed PMID: 24798930. 3: Miura M, Satoh S, Tada H, Habuchi T, Suzuki T. Stereoselective metabolism of rabeprazole-thioether to rabeprazole by human liver microsomes. Eur J Clin Pharmacol. 2006 Feb;62(2):113-7. Epub 2005 Dec 31. PubMed PMID: 16389533. 4: Thyssen A, Solanki B, Treem W. Randomized, open-label, single-dose, crossover, relative bioavailability study in healthy adults, comparing the pharmacokinetics of rabeprazole granules administered using soft food or infant formula as dosing vehicle versus suspension. Clin Ther. 2012 Jul;34(7):1636-45. doi: 10.1016/j.clinthera.2012.06.008. Epub 2012 Jun 29. PubMed PMID: 22748970. 5: Uno T, Yasui-Furukori N, Shimizu M, Sugawara K, Tateishi T. Determination of rabeprazole and its active metabolite, rabeprazole thioether in human plasma by column-switching high-performance liquid chromatography and its application to pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 25;824(1-2):238-43. PubMed PMID: 16087412. 6: Uno T, Shimizu M, Yasui-Furukori N, Sugawara K, Tateishi T. Different effects of fluvoxamine on rabeprazole pharmacokinetics in relation to CYP2C19 genotype status. Br J Clin Pharmacol. 2006 Mar;61(3):309-14. PubMed PMID: 16487224; PubMed Central PMCID: PMC1885025. 7: Miura M. Enantioselective disposition of lansoprazole and rabeprazole in human plasma. Yakugaku Zasshi. 2006 Jun;126(6):395-402. Review. PubMed PMID: 16755125. 8: Shimizu M, Uno T, Yasui-Furukori N, Sugawara K, Tateishi T. Effects of clarithromycin and verapamil on rabeprazole pharmacokinetics between CYP2C19 genotypes. Eur J Clin Pharmacol. 2006 Aug;62(8):597-603. Epub 2006 Jun 17. PubMed PMID: 16783561. 9: Li XQ, Andersson TB, Ahlström M, Weidolf L. Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. PubMed PMID: 15258107. 10: Ren S, Park MJ, Kim A, Lee BJ. In vitro metabolic stability of moisture-sensitive rabeprazole in human liver microsomes and its modulation by pharmaceutical excipients. Arch Pharm Res. 2008 Mar;31(3):406-13. doi: 10.1007/s12272-001-1171-z. Epub 2008 Apr 13. PubMed PMID: 18409057. 11: Niioka T, Uno T, Yasui-Furukori N, Shimizu M, Sugawara K, Tateishi T. Identification of the time-point which gives a plasma rabeprazole concentration that adequately reflects the area under the concentration-time curve. Eur J Clin Pharmacol. 2006 Oct;62(10):855-61. Epub 2006 Aug 17. PubMed PMID: 16915367. 12: Miura M, Tada H, Satoh S, Habuchi T, Suzuki T. Determination of rabeprazole enantiomers and their metabolites by high-performance liquid chromatography with solid-phase extraction. J Pharm Biomed Anal. 2006 May 3;41(2):565-70. Epub 2006 Jan 18. PubMed PMID: 16442771. 13: Lin CJ, Yang JC, Uang YS, Chern HD, Wang TH. Time-dependent amplified pharmacokinetic and pharmacodynamic responses of rabeprazole in cytochrome P450 2C19 poor metabolizers. Pharmacotherapy. 2003 Jun;23(6):711-9. PubMed PMID: 12820812. 14: Ohbuchi M, Noguchi K, Kawamura A, Usui T. Different effects of proton pump inhibitors and famotidine on the clopidogrel metabolic activation by recombinant CYP2B6, CYP2C19 and CYP3A4. Xenobiotica. 2012 Jul;42(7):633-40. doi: 10.3109/00498254.2011.653655. Epub 2012 Feb 7. PubMed PMID: 22313038.