2. Metabolic Enzyme/Protease Immunology/Inflammation Anti-infection
  3. Drug Metabolite Aryl Hydrocarbon Receptor Bacterial
  4. Omeprazole sulfide

Omeprazole sulfide  (Synonyms: Ufiprazole)

Cat. No.: HY-G0006 Purity: 99.88%
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Omeprazole sulfide (Ufiprazole) is a metabolic degradation product of Omeprazole (HY-B0113). Omeprazole sulfide acts as a modulator of AhR. Omeprazole sulfide in cells with low CYP3A4 expression, functions as an AhR antagonist; however, in cells with high CYP3A4 expression, it is rapidly metabolized to Omeprazole, thereby acting as an AhR agonist. Omeprazole sulfide exhibits antibacterial activity when conjugated with silver nanoparticles (AgNPs). Omeprazole sulfide can be used in research on acid suppression and bacterial infections.

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Omeprazole sulfide

Omeprazole sulfide Chemical Structure

CAS No. : 73590-85-9

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Based on 2 publication(s) in Google Scholar

Other Forms of Omeprazole sulfide:

Omeprazole sulfide Related Antibodies

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  • Biological Activity

  • Purity & Documentation

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Description

Omeprazole sulfide (Ufiprazole) is a metabolic degradation product of Omeprazole (HY-B0113). Omeprazole sulfide acts as a modulator of AhR. Omeprazole sulfide in cells with low CYP3A4 expression, functions as an AhR antagonist; however, in cells with high CYP3A4 expression, it is rapidly metabolized to Omeprazole, thereby acting as an AhR agonist. Omeprazole sulfide exhibits antibacterial activity when conjugated with silver nanoparticles (AgNPs). Omeprazole sulfide can be used in research on acid suppression and bacterial infections[1][2].

Cellular Effect
Cell Line Type Value Description References
HEK293 EC50
3900 nM
Compound: 1b
Agonist activity at recombinant BRS-3 receptor expressed in baculovirus-transduced HEK293 cells assessed as intracellular calcium mobilization by FLIPR assay
Agonist activity at recombinant BRS-3 receptor expressed in baculovirus-transduced HEK293 cells assessed as intracellular calcium mobilization by FLIPR assay
[PMID: 18818070]
In Vitro

Omeprazole sulfide (100 μM; 30 min) induces a unique conformational change in mouse AhR, resulting in a trypsin digestion pattern distinct from that of unliganded or agonist-bound receptors in Hepa-1c1c7 cell cytoplasmic extracts[1].
Omeprazole sulfide (15 μM; 2 h) blocks AhR-mediated nuclear translocation of mouse AhR in Hepa-1c1c7 cells[1].
Omeprazole sulfide (15 μM; 5.5 h) blocks TCDD-mediated degradation of mouse AhR and inhibits TCDD-induced CYP1A1 protein expression in Hepa-1c1c7 cells[1].
Omeprazole sulfide (5-50 μM; 8 h) acts as an AhR antagonist in mouse Hepa-1c1c7 and human HepG2 hepatocellular carcinoma cells, and inhibits TCDD-induced CYP1A1 mRNA expression in a concentration-dependent manner, with an inhibition rate of over 80% after treatment with 50 μM for 8 h[1].
Omeprazole sulfide (1-100 μM; 16 h) inhibits ligand-induced AhR transcriptional activity in mouse Hepa-1c1c7 and human HepG2 hepatocellular carcinoma cells, with an IC50 value of 1 to 10 μM after 16 h of incubation[1].
Omeprazole sulfide (1-50 μM; 8 h) inhibits agonist-induced conversion of mouse AhR to its DNA-binding form in cytoplasmic extracts of Hepa-1c1c7 cells, with complete inhibition achieved after treatment at 50 μM for 8 h[1].
Omeprazole sulfide (3-50 μM; 8 h) acts as an AhR agonist in freshly seeded primary human hepatocytes and induces CYP1A1 mRNA expression[1].
Omeprazole sulfide (5-60 μM; 8 h) switches from an AhR antagonist to an agonist in primary human hepatocytes depending on cellular metabolic capacity: it acts as an antagonist in low-metabolism control cells or ketoconazole-treated cells, whereas it functions as an agonist in rifampicin-pretreated cells with induced CYP3A4 activity[1].
Omeprazole sulfide forms stable spherical Ag@OMPS nanoparticles, which inhibit the growth of tested Gram-positive and Gram-negative bacterial strains, producing measurable inhibition zones with a maximum diameter of 5 mm[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Omeprazole sulfide Related Antibodies

Western Blot Analysis[1]

Cell Line: mouse Hepa-1c1c7 cell cytosolic extracts
Concentration: 100 μM
Incubation Time: 30 min (30°C, during trypsin digestion)
Result: Induced a distinct AhR proteolytic digest pattern, with the absence of a 23 kDa fragment that was present in unliganded or agonist-bound AhR samples.

Immunofluorescence[1]

Cell Line: mouse Hepa-1c1c7 cells
Concentration: 15 μM; 10 nM TCDD (co-treatment)
Incubation Time: 2 h
Result: Did not induce AhR nuclear translocation alone; blocked TCDD-mediated AhR nuclear translocation, keeping AhR localized in the cytosol when co-treated with TCDD.

Western Blot Analysis[1]

Cell Line: mouse Hepa-1c1c7 cells
Concentration: 15 μM; 1.5 nM TCDD (co-treatment)
Incubation Time: 1.5, 3.5, 5.5 h
Result: Did not alter AhR protein levels or induce CYP1A1 alone; blocked TCDD-mediated AhR degradation and inhibited CYP1A1 protein induction when co-treated with TCDD.
Molecular Weight

329.43

Formula

C17H19N3O2S
CAS No.
Appearance

Solid

Color

White to off-white

SMILES

CC(C(OC)=C(C)C=N1)=C1CSC2=NC3=CC=C(OC)C=C3N2
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 2 years
-20°C 1 year
Solvent & Solubility
In Vitro: 

DMSO : 100 mg/mL (303.55 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.0355 mL 15.1777 mL 30.3555 mL
5 mM 0.6071 mL 3.0355 mL 6.0711 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

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Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (7.59 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (7.59 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 3.0355 mL 15.1777 mL 30.3555 mL 75.8887 mL
5 mM 0.6071 mL 3.0355 mL 6.0711 mL 15.1777 mL
10 mM 0.3036 mL 1.5178 mL 3.0355 mL 7.5889 mL
15 mM 0.2024 mL 1.0118 mL 2.0237 mL 5.0592 mL
20 mM 0.1518 mL 0.7589 mL 1.5178 mL 3.7944 mL
25 mM 0.1214 mL 0.6071 mL 1.2142 mL 3.0355 mL
30 mM 0.1012 mL 0.5059 mL 1.0118 mL 2.5296 mL
40 mM 0.0759 mL 0.3794 mL 0.7589 mL 1.8972 mL
50 mM 0.0607 mL 0.3036 mL 0.6071 mL 1.5178 mL
60 mM 0.0506 mL 0.2530 mL 0.5059 mL 1.2648 mL
80 mM 0.0379 mL 0.1897 mL 0.3794 mL 0.9486 mL
100 mM 0.0304 mL 0.1518 mL 0.3036 mL 0.7589 mL
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Omeprazole sulfide Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Omeprazole sulfide73590-85-9UfiprazoleDrug MetaboliteAryl Hydrocarbon ReceptorBacterialAhRprimary human hepatocytesaryl hydrocarbon receptorCYP3A4CYP1A1 proteinmouse Hepa-1c1c7 cellshepatoma cellsnanocrystalline silver particleshuman HepG2 hepatoma cellsCYP1A mRNAInhibitorinhibitorinhibit

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