| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| Targets |
The primary target of Cimetidine sulfoxide is the histamine H2 receptor, for which it acts as an antagonist. As a metabolite of Cimetidine, it retains the ability to bind to H2 receptors, although with potentially different affinity compared to the parent compound. The H2 receptor is involved in gastric acid secretion, and its antagonism is the basis for the therapeutic effects of Cimetidine in peptic ulcer disease.
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| ln Vitro |
At lower substrate concentrations (40 and 200 μM), active transport of cimetidine was identified in the rat small intestine; at higher concentrations (400 μM), passive transport obscured the active transport. Following some incubation, cimetidine sulfoxide can be found [2].
In vitro, Cimetidine sulfoxide demonstrates H2-receptor antagonist activity, consistent with its role as a metabolite of Cimetidine. The compound is studied in vitro to understand the metabolic fate of Cimetidine and the pharmacological activity of its metabolites. It is used in enzyme assays to study sulfoxidation reactions and cytochrome P450-mediated metabolism. These in vitro activities support research on drug metabolism, pharmacokinetics, and the pharmacology of H2-receptor antagonists. |
| ln Vivo |
Cimetidine (30 mg/kg; p.o.) was given to male Wistar rats, and 24 hours later, the enantiomeric makeup of cimetidine sulfoxide was also identified in the urine of the rats. This example has an enantiomeric ratio of (+/-) 57:43[3].
In vivo, Cimetidine sulfoxide is formed as the primary metabolite of Cimetidine following oral administration. The compound contributes to the overall pharmacological effects of Cimetidine, although its specific in vivo activity may differ from the parent drug. It is excreted in urine and can be measured as a biomarker of Cimetidine metabolism. The compound is used in pharmacokinetic studies to assess metabolic pathways and drug clearance. |
| Enzyme Assay |
In vitro enzyme/receptor binding assays for Cimetidine sulfoxide include H2 receptor binding assays using radioligand competition studies. The compound is incubated with H2 receptor-expressing cell membranes and a labeled H2 receptor ligand (e.g., [3H]-tiotidine) at concentrations ranging from 0.1 nM-100 μM. Binding affinity (Ki) is determined by competitive displacement curves. Functional assays measure the compound's ability to inhibit histamine-induced cAMP production in H2 receptor-expressing cells. All assays include Cimetidine as a positive control and appropriate vehicle controls.
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| Cell Assay |
In vitro cell-based assays for Cimetidine sulfoxide are conducted using cells expressing the H2 receptor (e.g., gastric parietal cells or transfected cell lines). Cells are treated with Cimetidine sulfoxide at concentrations ranging from 0.01-100 μM, and H2 receptor-mediated signaling is assessed by measuring cAMP levels or downstream signaling markers. The compound's ability to inhibit histamine-induced responses is evaluated. Cell viability is assessed using standard assays. Experiments include Cimetidine as a positive control and vehicle controls. All experiments are performed in triplicate.
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| Animal Protocol |
In vivo animal studies with Cimetidine sulfoxide are limited, as the compound is primarily studied as a metabolite rather than a therapeutic agent. Pharmacokinetic studies in rodents or other species involve administering Cimetidine and measuring Cimetidine sulfoxide levels in plasma and urine. The compound is also used in drug interaction studies to assess the effects of other drugs on Cimetidine metabolism. Each group consists of 6-10 animals with appropriate controls. Direct administration of Cimetidine sulfoxide is less common.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Cimetidine sulfoxide include its formation as the primary metabolite of Cimetidine through hepatic sulfoxidation. The compound has a longer half-life than Cimetidine in some cases and is excreted primarily via renal elimination. Its formation and clearance are influenced by cytochrome P450 enzyme activity and renal function. The compound can be measured in plasma and urine as a biomarker of Cimetidine metabolism and clearance. Detailed PK parameters are available from Cimetidine metabolism studies.
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| Toxicity/Toxicokinetics |
Toxicological data for Cimetidine sulfoxide are derived from studies of Cimetidine metabolism. As a metabolite of an approved drug, it is considered to have a favorable safety profile at concentrations achieved following therapeutic Cimetidine dosing. No significant toxicity has been attributed specifically to Cimetidine sulfoxide. However, comprehensive toxicological studies of the metabolite alone are limited. As with all research chemicals, appropriate safety precautions should be taken during handling.
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| References |
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| Additional Infomation |
Cimetidine S-oxide is a sulfoxide. It is functionally related to cimetidine.
Cimetidine sulfoxide is the primary metabolite of Cimetidine, a well-known histamine H2-receptor antagonist used clinically for peptic ulcer disease and upper gastrointestinal hemorrhage. The compound is used in research to study drug metabolism, pharmacokinetics, and the pharmacology of H2-receptor antagonists. It is also used as a reference standard in analytical method development for quantifying Cimetidine and its metabolites. Not approved as a therapeutic agent; intended for research purposes only. |
| Molecular Formula |
C10H16N6OS
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|---|---|
| Molecular Weight |
341.26100
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| Exact Mass |
340.063
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| CAS # |
54237-72-8
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| PubChem CID |
62949
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| Appearance |
White to off-white solid powder
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| Density |
1.39g/cm3
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| Boiling Point |
608.6ºC at 760mmHg
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| Flash Point |
321.8ºC
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| Index of Refraction |
1.665
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| LogP |
2.864
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
18
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| Complexity |
363
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
HOJLJLYVNQFCRE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H16N6OS/c1-8-9(16-7-15-8)5-18(17)4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
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| Chemical Name |
1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfinyl]ethyl]guanidine
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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) |
DMSO : ~83.33 mg/mL (~310.54 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (9.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9303 mL | 14.6516 mL | 29.3032 mL | |
| 5 mM | 0.5861 mL | 2.9303 mL | 5.8606 mL | |
| 10 mM | 0.2930 mL | 1.4652 mL | 2.9303 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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