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| Other Sizes |
| Targets |
16α-Hydroxyprednisolone targets the glucocorticoid receptor (GR), a nuclear receptor that regulates gene expression. Upon binding to the GR, the compound modulates the transcription of anti-inflammatory genes (transactivation) and represses the expression of pro-inflammatory genes (transrepression) through interactions with transcription factors such as NF-κB and AP-1. Its formation is catalyzed by cytochrome P450 3A (CYP3A) isoenzymes from budesonide. The 16α modification enhances its receptor binding affinity and therapeutic index.
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| ln Vitro |
In vitro, 16α-Hydroxyprednisolone exhibits potent glucocorticoid activity, including anti-inflammatory and immunosuppressive effects. As a glucocorticoid receptor agonist, it modulates the expression of numerous genes involved in inflammatory and immune responses. The compound's in vitro potency is comparable to that of other synthetic glucocorticoids. It inhibits the production of pro-inflammatory cytokines (e.g., IL-1, IL-6, TNF-α) and promotes the expression of anti-inflammatory mediators such as lipocortin-1 and IL-10.
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| ln Vivo |
In vivo, 16α-Hydroxyprednisolone demonstrates anti-inflammatory and immunosuppressive properties. As a glucocorticoid, it reduces inflammation in various animal models of inflammatory disease. The compound has been used in the treatment of inflammatory and autoimmune conditions. Its effects are mediated through glucocorticoid receptor activation, leading to the suppression of immune cell activation and inflammatory mediator production. The compound has been studied for the treatment of central nervous system disorders.
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| Enzyme Assay |
General protocols for glucocorticoid receptor binding assays use cytosolic preparations from rat liver or recombinant GR expressed in mammalian cells. Cytosol is incubated with [3H]dexamethasone (a radiolabeled glucocorticoid) and varying concentrations of 16α-Hydroxyprednisolone in binding buffer (10 mM Tris-HCl pH 7.4, 10 mM Na2MoO4, 1 mM EDTA, 5 mM DTT) at 4°C for 16-24 hours. Bound ligand is separated from free ligand using dextran-coated charcoal or hydroxylapatite. Radioactivity is counted, and IC50 values are calculated. Specific binding is determined by subtracting nonspecific binding (in the presence of 100-fold excess unlabeled dexamethasone).
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| Cell Assay |
General protocols for glucocorticoid activity in cell-based systems use reporter gene assays. Cells transfected with a glucocorticoid response element (GRE)-luciferase reporter construct and GR expression vector are treated with various concentrations of 16α-Hydroxyprednisolone for 24 hours. Luciferase activity is measured using a luminometer, and EC50 values are calculated from dose-response curves. Alternatively, cytokine production assays use LPS-stimulated macrophages or peripheral blood mononuclear cells treated with the compound for 24 hours, followed by ELISA measurement of TNF-α, IL-6, and IL-1β in culture supernatants.
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| Animal Protocol |
General protocols for in vivo anti-inflammatory activity use the carrageenan-induced paw edema model in rats. Rats are injected with 0.1 mL of 1% carrageenan solution into the subplantar region of the hind paw. 16α-Hydroxyprednisolone is administered orally or intraperitoneally at doses of 1-10 mg/kg 1 hour before carrageenan injection. Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, and 6 hours post-injection. The percentage inhibition of edema is calculated compared to vehicle-treated controls. Prednisolone or dexamethasone serves as positive controls.
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| ADME/Pharmacokinetics |
16α-Hydroxyprednisolone is a metabolite rather than a parent drug. As a glucocorticoid, it is expected to have pharmacokinetic properties similar to other synthetic corticosteroids. Following administration of budesonide, 16α-Hydroxyprednisolone is formed via CYP3A-mediated metabolism. The compound has moderate oral bioavailability and undergoes extensive hepatic metabolism. It is highly protein bound (primarily to corticosteroid-binding globulin and albumin). Elimination occurs via renal excretion of metabolites. The half-life is several hours.
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| Toxicity/Toxicokinetics |
16α-Hydroxyprednisolone, as a glucocorticoid, has a toxicity profile consistent with other corticosteroids. Long-term use can lead to adrenal suppression, Cushing's syndrome, osteoporosis, hyperglycemia, immunosuppression, and increased infection risk. Acute toxicity is rare but may include gastrointestinal bleeding, hypertension, and psychiatric disturbances. The compound should be used with caution in patients with diabetes, hypertension, osteoporosis, or infections. Dose tapering is required to avoid adrenal crisis upon discontinuation.
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| Additional Infomation |
16α-Hydroxyprednisolone (OH-PRED) is a drug metabolite rather than a marketed pharmaceutical product. It is primarily used as a research tool to study glucocorticoid metabolism and pharmacology. The compound is a stereoselective metabolite of budesonide, formed via cytochrome P450 3A (CYP3A) enzymes. It has been investigated for anti-inflammatory and immunosuppressive properties. It has not been approved for clinical use as a standalone therapeutic agent. Its applications are limited to research and development purposes.
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| Molecular Formula |
C21H28O6
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|---|---|
| Molecular Weight |
376.44
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| Exact Mass |
376.188
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| CAS # |
13951-70-7
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| PubChem CID |
11047056
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
591.5±50.0 °C at 760 mmHg
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| Melting Point |
235-238ºC
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| Flash Point |
325.6±26.6 °C
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| Vapour Pressure |
0.0±3.8 mmHg at 25°C
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| Index of Refraction |
1.630
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| LogP |
0.95
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| Hydrogen Bond Donor Count |
4
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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 |
756
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| Defined Atom Stereocenter Count |
8
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| SMILES |
O([H])[C@@]1(C(C([H])([H])O[H])=O)[C@]([H])(C([H])([H])[C@]2([H])[C@@]3([H])C([H])([H])C([H])([H])C4=C([H])C(C([H])=C([H])[C@@]4(C([H])([H])[H])[C@]3([H])[C@@]([H])(C([H])([H])[C@]21C([H])([H])[H])O[H])=O)O[H]
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| InChi Key |
SEKYBDYVXDAYPY-ILNISADRSA-N
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| InChi Code |
InChI=1S/C21H28O6/c1-19-6-5-12(23)7-11(19)3-4-13-14-8-16(25)21(27,17(26)10-22)20(14,2)9-15(24)18(13)19/h5-7,13-16,18,22,24-25,27H,3-4,8-10H2,1-2H3/t13-,14-,15-,16+,18+,19-,20-,21-/m0/s1
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| Chemical Name |
(8S,9S,10R,11S,13S,14S,16R,17S)-11,16,17-Trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
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| Synonyms |
16alpha Hydroxyprednisolone16alpha-Hydroxyprednisolone OH PRED OH-PRED
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 : ~100 mg/mL (~265.65 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.64 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 (6.64 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 (6.64 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 | 2.6565 mL | 13.2823 mL | 26.5647 mL | |
| 5 mM | 0.5313 mL | 2.6565 mL | 5.3129 mL | |
| 10 mM | 0.2656 mL | 1.3282 mL | 2.6565 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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