| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 500mg | |||
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| Targets |
4-Hydroxytolbutamide acts primarily as an antidiabetic agent and is involved in glucose metabolism by functioning as a potassium channel blocker, influencing insulin secretion from pancreatic beta-cells. As a metabolite of tolbutamide, it shares the sulfonylurea mechanism of action: blocking ATP-sensitive potassium channels on pancreatic beta cells, leading to depolarization, calcium influx, and insulin release. However, 4-hydroxytolbutamide has significantly lower hypoglycemic activity than the parent drug tolbutamide.
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| ln Vitro |
In vitro, 4-hydroxytolbutamide is formed from tolbutamide by CYP2C9 in human liver microsomes and COS-7 cells. Its formation can be used as a marker of CYP2C9 activity in vitro. The compound itself has lower hypoglycemic activity than tolbutamide. It is used as a reference standard in analytical method development for the quantification of tolbutamide and its metabolites in biological samples.
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| ln Vivo |
In vivo, 4-hydroxytolbutamide is a metabolite of tolbutamide formed in the body. Tolbutamide is administered orally and is metabolized to 4-hydroxytolbutamide, which is then further metabolized and excreted. As a metabolite, 4-hydroxytolbutamide contributes to the overall pharmacological effects of tolbutamide, though with lower hypoglycemic activity. It is involved in glucose metabolism by functioning as a potassium channel blocker.
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| Enzyme Assay |
In non-cell-based enzyme assays, 4-hydroxytolbutamide formation is used to measure CYP2C9 activity. Human liver microsomes or recombinant CYP2C9 enzyme are incubated with tolbutamide, NADPH, and varying concentrations of inhibitors. The formation of 4-hydroxytolbutamide is quantified using HPLC or LC-MS/MS. The compound can also be used as a reference standard in analytical chemistry for the development and validation of methods to quantify tolbutamide and its metabolites.
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| Cell Assay |
In vitro cellular assays for 4-hydroxytolbutamide involve testing its effects on insulin secretion from pancreatic beta cells. Insulinoma cell lines or primary pancreatic islet cells are treated with varying concentrations of 4-hydroxytolbutamide, and insulin secretion is measured using ELISA or radioimmunoassay. The compound's ability to stimulate insulin release is compared to that of tolbutamide. However, 4-hydroxytolbutamide has significantly lower hypoglycemic activity than tolbutamide.
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| Animal Protocol |
In vivo animal studies for 4-hydroxytolbutamide are limited, as the compound is a metabolite rather than a therapeutic agent. When studied, it is typically administered to animals to assess its pharmacokinetics, metabolism, and glucose-lowering effects. Tolbutamide is administered orally, and the formation of 4-hydroxytolbutamide is measured in plasma and urine to assess metabolic clearance. The compound's effects are compared to those of tolbutamide.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
4-Hydroxytoluamide is a known metabolite of toluenebutyrate in the human body. 4-Hydroxytolbutamide has a molecular weight of 286.34 and a molecular formula of C12H18N2O4S. It is a white to off-white solid powder with a melting point of 100-102°C. It has a logP of 0.7, indicating low lipophilicity. The compound is soluble in DMSO. It should be stored as a powder at -20°C for 3 years or 4°C for 2 years. It is metabolized by CYP2C8 and CYP2C9. |
| Toxicity/Toxicokinetics |
As a metabolite and research compound, 4-hydroxytolbutamide is not intended for human use. Comprehensive toxicology studies have not been extensively published, but the compound is generally considered safe for laboratory use. It should be handled with appropriate safety precautions, including the use of personal protective equipment. Its safety profile is consistent with that of other sulfonylurea metabolites.
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| Additional Infomation |
4-Hydroxytosulfonamide is a urea compound composed of 1-butylurea with a 4-hydroxymethylbenzenesulfonyl group attached at the 3-position. It is a metabolite. It belongs to the sulfonamide, urea, and benzyl alcohol classes. There are reports and relevant data regarding 4-hydroxytosulfonamide in humans.
4-Hydroxytolbutamide (Hydroxytolbutamide) is a metabolite of tolbutamide, a first-generation potassium channel blocker and sulfonylurea oral hypoglycemic agent. It is formed by CYP2C8 and CYP2C9. 4-Hydroxytolbutamide acts as an antidiabetic agent and is involved in glucose metabolism by functioning as a potassium channel blocker, influencing insulin secretion from pancreatic beta-cells. It has significantly lower hypoglycemic activity than tolbutamide. |
| Molecular Formula |
C12H18N2O4S
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|---|---|
| Molecular Weight |
286.34
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| Exact Mass |
286.098
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| CAS # |
5719-85-7
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| Related CAS # |
4-Hydroxytolbutamide-d9;1185112-19-9
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| PubChem CID |
3656
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Melting Point |
100-102ºC
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| Flash Point |
2℃
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| Index of Refraction |
1.553
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| LogP |
0.7
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
19
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| Complexity |
370
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCNC(NS(=O)(C1=CC=C(CO)C=C1)=O)=O
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| InChi Key |
SJRHYONYKZIRPM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H18N2O4S/c1-2-3-8-13-12(16)14-19(17,18)11-6-4-10(9-15)5-7-11/h4-7,15H,2-3,8-9H2,1H3,(H2,13,14,16)
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| Chemical Name |
N-(Butylaminocarbonyl)-4-hydroxymethylbenzenesulfonamide
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| Synonyms |
4 Hydroxytolbutamide 4 ydroxytolbutamide 4-Hydroxytolbutamide
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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 | 3.4924 mL | 17.4618 mL | 34.9235 mL | |
| 5 mM | 0.6985 mL | 3.4924 mL | 6.9847 mL | |
| 10 mM | 0.3492 mL | 1.7462 mL | 3.4924 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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