| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
5‑Hydroxyomeprazole does not inhibit the gastric H+/K+ ATPase (the target of omeprazole) significantly, as hydroxylation reduces the compound's ability to form the active sulfenamide species that irreversibly binds to the proton pump. It is an inactive metabolite. The compound is primarily used as an analytical standard to quantify CYP2C19 activity, as its formation from omeprazole reflects the activity of this polymorphic enzyme.
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| ln Vitro |
In vitro, 5‑Hydroxyomeprazole is used as a standard in HPLC and LC‑MS assays for the quantification of omeprazole and its metabolites in biological samples. A typical chromatographic method uses a C18 column, a mobile phase of 10 mM ammonium formate (pH 3.0) and acetonitrile, and detection at 302 nm. The retention time of 5‑hydroxyomeprazole is approximately 2.4 min under standard conditions (1.0 mL/min flow rate, 28 degC).
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| ln Vivo |
5‑Hydroxyomeprazole is not a drug; it is a research standard. In animal studies, it is not administered directly; rather, omeprazole is administered, and the ratio of 5‑hydroxyomeprazole to omeprazole in plasma (or the metabolic ratio) is used to assess CYP2C19 function. This is particularly relevant in humanized mouse models expressing CYP2C19 polymorphisms. The metabolite is excreted in urine and feces; its half‑life parallels that of omeprazole (0.5‑1 h in humans).
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| Enzyme Assay |
CYP2C19‑mediated metabolism of omeprazole to 5‑hydroxyomeprazole is assessed in human liver microsomes (HLMs). A typical assay: 0.5 mg/mL HLMs are incubated with 10 microM omeprazole and an NADPH‑regenerating system in 100 mM potassium phosphate buffer (pH 7.4) at 37 degC for 30 min. The reaction is stopped with acetonitrile, and the formation of 5‑hydroxyomeprazole is quantified by LC‑MS/MS. The assay can be performed with or without an inhibitor to assess enzyme activity.
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| Cell Assay |
5‑Hydroxyomeprazole is not used in cell‑based assays to produce a biological effect. It can be added to cell culture media as a reference compound for LC‑MS method validation. For hepatocyte metabolism studies, primary human hepatocytes are incubated with omeprazole (10 microM) for 2 h, and the culture medium is analyzed for 5‑hydroxyomeprazole. The level of the metabolite correlates with the CYP2C19 activity of the hepatocyte donor (e.g., poor vs extensive metabolizer).
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| Animal Protocol |
5‑Hydroxyomeprazole is not administered directly to animals. For phenotyping studies, omeprazole (10‑20 mg/kg) is administered orally or intraperitoneally to rats or mice. Blood samples are collected at multiple time points (0, 15, 30, 60, 120, 240 min). Plasma is analyzed for omeprazole and 5‑hydroxyomeprazole. The metabolic ratio (5‑hydroxyomeprazole/omeprazole) is calculated at each time point. Animals with low CYP2C19 activity show a reduced metabolic ratio.
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| ADME/Pharmacokinetics |
Omeprazole (20 mg/kg, oral) in rats is rapidly absorbed (Tmax 0.5‑1 h). The half‑life of omeprazole is 0.5‑1 h. 5‑Hydroxyomeprazole appears in plasma within 15 min, with a Cmax approximately 10‑20% that of omeprazole. The metabolite is cleared by renal excretion and further metabolism (conjugation). Its half‑life is similar to omeprazole (0.5‑1 h). The metabolic ratio varies widely depending on CYP2C19 genotype. The parent chelator has no intrinsic PK.
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| Toxicity/Toxicokinetics |
5‑Hydroxyomeprazole sodium has low toxicity as it is a naturally occurring human metabolite. The oral LD₅0 is not established, but omeprazole (parent drug) has an LD₅0 >2000 mg/kg in rats. At therapeutic doses, 5‑hydroxyomeprazole levels are very low and not associated with adverse effects. As a laboratory standard, it may be a skin and eye irritant. Standard precautions (gloves, goggles, lab coat) should be used. It is not for human consumption.
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| References | |
| Additional Infomation |
5‑Hydroxyomeprazole sodium is not a drug; it is an analytical reference standard and drug metabolite. It is used for quality control in pharmaceutical analysis, for phenotyping CYP2C19 activity in clinical research, and for studying drug‑drug interactions involving CYP2C19. The level of 5‑hydroxyomeprazole in plasma can be used to determine the degree of omeprazole metabolism and to classify individuals as poor, intermediate, or extensive metabolizers. It is also used as an impurity reference standard for omeprazole.
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| Molecular Formula |
C17H18N3NAO4S
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|---|---|
| Molecular Weight |
383.40
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| Exact Mass |
383.092
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| CAS # |
1215629-45-0
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| PubChem CID |
46781846
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
3.387
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
26
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| Complexity |
475
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=C(C(=CN=C1CS(=O)C2=NC3=C([N-]2)C=CC(=C3)OC)CO)OC.[Na+]
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| InChi Key |
DUXRBEBEUHQJMS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H18N3O4S.Na/c1-10-15(18-7-11(8-21)16(10)24-3)9-25(22)17-19-13-5-4-12(23-2)6-14(13)20-17;/h4-7,21H,8-9H2,1-3H3;/q-1;+1
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| Chemical Name |
sodium;[4-methoxy-6-[(5-methoxybenzimidazol-1-id-2-yl)sulfinylmethyl]-5-methylpyridin-3-yl]methanol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6082 mL | 13.0412 mL | 26.0824 mL | |
| 5 mM | 0.5216 mL | 2.6082 mL | 5.2165 mL | |
| 10 mM | 0.2608 mL | 1.3041 mL | 2.6082 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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