| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Glucocorticoid receptor; metabolite of Budesonide
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| ln Vivo |
Budesonide (BUD) is a glucocorticoid widely used for the treatment of asthma, rhinitis, and inflammatory bowel disease. Its use in sport competitions is prohibited when administered by oral, intravenous, intramuscular, or rectal routes. However, topical preparations are not prohibited. Strategies to discriminate between legal and forbidden administrations have to be developed by doping control laboratories. For this reason, metabolism of BUD has been re-evaluated using liquid chromatography-tandem mass spectrometry (LC-MS/MS) with different scan methods. Urine samples obtained after oral administration of 3 mg of BUD to two healthy volunteers have been analyzed for metabolite detection in free and glucuronide metabolic fractions. Structures of the metabolites have been studied by LC-MS/MS using collision induced dissociation and gas chromatography-mass spectrometry (GC/MS) in full scan mode with electron ionization. Combination of all structural information allowed the proposition of the most comprehensive picture for BUD metabolism in humans to this date. Overall, 16 metabolites including ten previously unreported compounds have been detected. The main metabolite is 16α-hydroxy-prednisolone resulting from the cleavage of the acetal group. Other metabolites without the acetal group have been identified such as those resulting from reduction of C20 carbonyl group, oxidation of the C11 hydroxyl group and reduction of the A ring. Metabolites maintaining the acetal group have also been identified, resulting from 6-hydroxylation (6α and 6β-hydroxy-budesonide), 23-hydroxylation, reduction of C6-C7, oxidation of the C11 hydroxyl group, and reduction of the C20 carbonyl group. Metabolites were mainly excreted in the free fraction. All of them were excreted in urine during the first 24 h after administration, and seven of them were still detected up to 48 h after administration for both volunteers [1].
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| References | |
| Additional Infomation |
This study employed liquid chromatography-tandem mass spectrometry (LC-MS/MS) combined with gas chromatography-mass spectrometry (GC/MS) to identify some metabolites and investigated the metabolism of budesonide (BUD). Based on all collected information, the overall metabolism of BUD was reassessed. Sixteen metabolites were detected in urine samples after oral administration of BUD. By comparing with commercially available standards, the structures of the metabolite resulting from acetal chain cleavage (MI, 16α-hydroxyprednisolone) and the metabolites resulting from 6-hydroxylation (M-II and M-III, 6β-hydroxybudesonide and 6α-hydroxybudesonide, respectively) were confirmed. The possible structures of the remaining metabolites were proposed based on mass spectrometry data. Some metabolites that maintain the acetal chain structure are generated via acetal chain hydroxylation (M-IVa, M-IVb, M-Va, and M-Vb), C6-C7 reduction (M-Va, M-Vb, and M-VI), C11 hydroxyl oxidation (M-VII), or C20 carbonyl reduction (M-VIII). Other metabolites are generated via acetal chain cleavage (e.g., MI) and other modifications (C20 carbonyl reduction, M-IXa and M-IXb; C11 hydroxyl oxidation, MX; or A-ring reduction, M-XI to M-XIII). Ten of these metabolites have not been previously reported with ibuprofen (M-III, M-Va, M-Vb, M-VII, MVIII, MIXa, MIXb, MXI, MXII, and MXIII). A better understanding of budesonide metabolism will help in investigating differences in metabolites in urinary samples under different routes of administration. These differences could be used to develop analytical strategies to differentiate between the legal and prohibited use of dine-iodine in doping control analysis. [1]
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| Molecular Formula |
C21H26O6
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|---|---|
| Molecular Weight |
374.43
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| CAS # |
3754-05-0
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| PubChem CID |
71752789
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| Appearance |
Solid powder
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| LogP |
0.737
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
27
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| Complexity |
796
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| Defined Atom Stereocenter Count |
7
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| SMILES |
OC1CC2C(C)(CC(=O)C3C2CCC2C3(C)C=CC(=O)C=2)C1(O)C(=O)CO
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| Synonyms |
3754-05-0; 11-Keto-16alpha-hydroxyprednisolone; 16alpha,17,21-Trihydroxy-pregna-1,4-diene-3,11,20-trione; UNII-9UUI9HUO3Q; 9UUI9HUO3Q; (8S,9S,10R,13S,14S,16R,17S)-16,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione; Pregna-1,4-diene-3,11,20-trione, 16,17,21-trihydroxy-, (16alpha)-; 16a,17,21-Trihydroxy-pregna-1,4-diene-3,11,20-trione;
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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 : ~116.67 mg/mL (~311.59 mM; with ultrasonication)
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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 | 2.6707 mL | 13.3536 mL | 26.7073 mL | |
| 5 mM | 0.5341 mL | 2.6707 mL | 5.3415 mL | |
| 10 mM | 0.2671 mL | 1.3354 mL | 2.6707 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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