Prednison
Übersicht
Beschreibung
Prednisone is a synthetic glucocorticoid used primarily for its anti-inflammatory and immunosuppressive properties . It is a prodrug that is metabolized in the liver to its active form, prednisolone . Prednisone is widely used in the treatment of various conditions such as asthma, chronic obstructive pulmonary disease, rheumatologic diseases, and certain types of cancer .
Wirkmechanismus
Target of Action
Prednisone is a synthetic anti-inflammatory glucocorticoid derived from cortisone . It primarily targets the glucocorticoid receptors in the body . These receptors are found in almost every cell and are critical for numerous biological responses including metabolism, inflammation, and immune response .
Mode of Action
Prednisone itself is biologically inert and must be converted to prednisolone in the liver before it becomes active . Prednisolone then binds to glucocorticoid receptors, activating them and triggering changes in gene expression . This binding inhibits pro-inflammatory signals and promotes anti-inflammatory signals .
Biochemical Pathways
The anti-inflammatory action of prednisolone is mediated by the inhibition of prostaglandin synthesis . This occurs via two actions on the arachidonic acid pathway. Firstly, prednisolone inhibits specific transcription factors, AP-1 and NF-kB, involved in the regulation of pro-inflammatory proteins, including inducible cyclo-oxygenase-2 .
Pharmacokinetics
Prednisone has a bioavailability of 70% . It is metabolized in the liver to its active form, prednisolone . The elimination half-life of prednisone is 2 to 3 hours in adults . Prednisone is excreted in the urine as conjugates . The time to peak for oral prednisone is 2 hours for immediate-release tablets and 6 to 6.5 hours for delayed-release tablets .
Result of Action
The result of prednisone’s action is a decrease in inflammation and suppression of the immune system . This is achieved by suppressing the migration of polymorphonuclear leukocytes and reversing increased capillary permeability . It also reduces the activity and volume of the lymphatic system . These effects make prednisone effective in treating a variety of conditions, including allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, infectious, endocrine, or neoplastic conditions .
Action Environment
The action of prednisone can be influenced by various environmental factors. For instance, its absorption may be altered in conditions such as hepatic failure, chronic renal failure, inflammatory bowel disease, hyperthyroidism, and in the elderly . Furthermore, the conversion of prednisone to prednisolone may be impaired in patients with liver disease . Therefore, the action, efficacy, and stability of prednisone can be influenced by the patient’s health status and age, among other factors.
Wissenschaftliche Forschungsanwendungen
Prednison hat eine breite Palette von Anwendungen in der wissenschaftlichen Forschung:
Chemie: Wird als Referenzverbindung bei der Untersuchung von Glukokortikoiden und deren Derivaten verwendet.
Biologie: Untersucht auf seine Auswirkungen auf zelluläre Prozesse und die Genexpression.
5. Wirkmechanismus
This compound entfaltet seine Wirkung, indem es in der Leber in Prednisolon umgewandelt wird . Prednisolon bindet dann an Glukokortikoidrezeptoren, aktiviert diese und löst Veränderungen in der Genexpression aus . Dies führt zur Unterdrückung der Migration von polymorphkernigen Leukozyten und zur Umkehrung der erhöhten Kapillarpermeabilität, wodurch Entzündungen reduziert werden . Es unterdrückt auch das Immunsystem, indem es die Aktivität und das Volumen des Immunsystems reduziert .
Ähnliche Verbindungen:
- Dexamethason
- Methotrexat
- Mycophenolat
- Mercaptopurin
- Azathioprin
- Leflunomid
Vergleich: this compound ist einzigartig in seiner Fähigkeit, in eine aktive Form, Prednisolon, umgewandelt zu werden, die starke entzündungshemmende und immunsuppressive Wirkungen hat . Im Vergleich zu Dexamethason hat this compound eine kürzere Halbwertszeit und ist weniger potent . Methotrexat und Mycophenolat werden in erster Linie als Immunsuppressiva eingesetzt, haben aber nicht die gleichen entzündungshemmenden Eigenschaften wie this compound . Mercaptopurin, Azathioprin und Leflunomid werden ebenfalls als Immunsuppressiva eingesetzt, haben jedoch unterschiedliche Wirkmechanismen und werden in verschiedenen klinischen Kontexten verwendet .
Biochemische Analyse
Biochemical Properties
Prednisone interacts with various enzymes, proteins, and other biomolecules. It is metabolized to its active form, prednisolone, in the liver through the 11-hydroxysteroid dehydrogenase enzyme (HSD11B1) . Prednisolone then binds to glucocorticoid receptors, activating them and triggering changes in gene expression .
Cellular Effects
Prednisone influences cell function by suppressing virtually every component of the inflammatory process . It inhibits the synthesis of interleukins and numerous other proinflammatory cytokines, suppresses cell-mediated immunity, reduces complement synthesis, and decreases production and activity of leukocytes .
Molecular Mechanism
Prednisone exerts its effects at the molecular level through binding interactions with biomolecules and changes in gene expression. Prednisone is a prodrug and must be converted to prednisolone by the liver before it becomes active . Prednisolone then binds to glucocorticoid receptors, activating them and triggering changes in gene expression .
Temporal Effects in Laboratory Settings
The effects of prednisone change over time in laboratory settings. For example, a study showed that even short-term, low dosage use of prednisone was associated with higher rates of sepsis, venous thromboembolism, and fractures within 30 days of starting on steroids .
Dosage Effects in Animal Models
The effects of prednisone vary with different dosages in animal models. A study on dogs showed that prednisone concentrations in various tissues were increased or decreased depending on the dosage and the specific tissue .
Metabolic Pathways
Prednisone is involved in various metabolic pathways. It is converted to its active metabolite prednisolone in the liver through the 11-hydroxysteroid dehydrogenase enzyme (HSD11B1) . Prednisolone is further metabolized primarily via cytochrome P450 enzyme CYP3A (CYP3A4 and possibly CYP3A5) .
Transport and Distribution
Prednisone is transported and distributed within cells and tissues. A study showed that the tissue distribution of prednisone and prednisolone was affected by certain factors, leading to increased or decreased concentrations in various tissues .
Subcellular Localization
The subcellular localization of prednisone and its effects on its activity or function are complex. Prednisone is a prodrug and must be converted to prednisolone by the liver before it becomes active . Prednisolone then binds to glucocorticoid receptors, which are located in the cytoplasm of cells, and the receptor-ligand complex then translocates to the nucleus, where it regulates gene expression .
Vorbereitungsmethoden
Synthetic Routes and Reaction Conditions: The preparation of prednisone typically involves several steps starting from a mold oxide. The process includes a Platts oxidation reaction, followed by a bromine addition reaction, bromine removal, and a 21-bit iodine addition reaction . The final step involves a 21-bit replacement reaction to obtain prednisone .
Industrial Production Methods: Industrial production of prednisone often involves the use of hydrocortisone acetate as a starting material . The process includes steps such as oxidation, reduction, and esterification to produce prednisone on a large scale . The methods are designed to minimize waste and reduce environmental impact by recycling chromium and acetic acid .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Prednison unterliegt verschiedenen chemischen Reaktionen, darunter Oxidation, Reduktion und Substitution .
Häufige Reagenzien und Bedingungen:
Oxidation: Platts-Oxidationsreaktion unter Verwendung von Schimmelpilzoxid.
Substitution: Bromzugabe- und -entfernungsreaktionen sind bei der Synthese von this compound üblich.
Hauptprodukte: Das Hauptprodukt, das aus diesen Reaktionen gebildet wird, ist this compound selbst, das dann weiter zu seiner aktiven Form, Prednisolon, verarbeitet wird .
Vergleich Mit ähnlichen Verbindungen
- Dexamethasone
- Methotrexate
- Mycophenolate
- Mercaptopurine
- Azathioprine
- Leflunomide
Comparison: Prednisone is unique in its ability to be converted to an active form, prednisolone, which has potent anti-inflammatory and immunosuppressive effects . Compared to dexamethasone, prednisone has a shorter half-life and is less potent . Methotrexate and mycophenolate are primarily used as immunosuppressants but do not have the same anti-inflammatory properties as prednisone . Mercaptopurine, azathioprine, and leflunomide are also used as immunosuppressants but have different mechanisms of action and are used in different clinical contexts .
Eigenschaften
IUPAC Name |
(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XOFYZVNMUHMLCC-ZPOLXVRWSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC12CC(=O)C3C(C1CCC2(C(=O)CO)O)CCC4=CC(=O)C=CC34C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
C[C@]12CC(=O)[C@H]3[C@H]([C@@H]1CC[C@@]2(C(=O)CO)O)CCC4=CC(=O)C=C[C@]34C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C21H26O5 |
Source
|
| Record name | PREDNISONE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20949 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID4021185 |
Source
|
| Record name | Prednisone | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID4021185 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
358.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Prednisone is an odorless white crystalline powder. (NTP, 1992), Solid |
Source
|
| Record name | PREDNISONE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20949 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Prednisone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014773 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Solubility |
Very slightly soluble (NTP, 1992), Very slightly soluble, Very slightly soluble in water; 1 g soluble in 150 mL alcohol, in 200 mL chloroform; slightly soluble in methanol, 1.11e-01 g/L |
Source
|
| Record name | PREDNISONE | |
| Source | CAMEO Chemicals | |
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| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Prednisone | |
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| Record name | PREDNISONE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3168 | |
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| Record name | Prednisone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014773 | |
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Mechanism of Action |
Prednisone is first metabolized in the liver to its active form, prednisolone, a glucocorticoid agonist corticosteroid. The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days. Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10. Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels., In physiologic doses, corticosteroids are administered to replace deficient endogenous hormones. In larger (pharmacologic) doses, glucocorticoids decrease inflammation by stabilizing leukocyte lysosomal membranes, preventing release of destructive acid hydrolases from leukocytes; inhibiting macrophage accumulation in inflamed areas; reducing leukocyte adhesion to capillary endothelium; reducing capillary wall permeability and edema formation; decreasing complement components; antagonizing histamine activity and release of kinin from substrates; reducing fibroblast proliferation, collagen deposition, and subsequent scar tissue formation; and possibly by other mechanisms as yet unknown. The drugs suppress the immune response by reducing activity and volume of the lymphatic system, producing lymphocytopenia, decreasing immunoglobulin and complement concentrations, decreasing passage of immune complexes through basement membranes, and possibly by depressing reactivity of tissue to antigen-antibody interactions. Glucocorticoids stimulate erythroid cells of bone marrow, prolong survival time of erythrocytes and platelets, and produce neutrophilia and eosinopenia. Glucocorticoids promote gluconeogenesis, redistribution of fat from peripheral to central areas of the body, and protein catabolism, which results in negative nitrogen balance. They reduce intestinal absorption and increase renal excretion of calcium. /Corticosteroids/, Glucocorticoids are capable of suppressing the inflammatory process through numerous pathways. They interact with specific intracellular receptor proteins in target tissues to alter the expression of corticosteroid-responsive genes. Glucocorticoid-specific receptors in the cell cytoplasm bind with steroid ligands to form hormone-receptor complexes that eventually translocate to the cell nucleus. There these complexes bind to specific DNA sequences and alter their expression. The complexes may induce the transcription of mRNA leading to synthesis of new proteins. Such proteins include lipocortin, a protein known to inhibit PLA2a and thereby block the synthesis of prostaglandins, leukotrienes, and PAF. Glucocorticoids also inhibit the production of other mediators including AA metabolites such as COX, cytokines, the interleukins, adhesion molecules, and enzymes such as collagenase. /Glucocorticoids/ |
Source
|
| Record name | Prednisone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00635 | |
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| Record name | PREDNISONE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3168 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Crystals, White to practically white, crystalline powder | |
CAS No. |
53-03-2 |
Source
|
| Record name | PREDNISONE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20949 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | PREDNISONE | |
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| Record name | Prednisone | |
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Melting Point |
451 to 455 °F (DEC) (NTP, 1992), 234 °C (decomposes), 233 - 235 °C |
Source
|
| Record name | PREDNISONE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20949 | |
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| Record name | Prednisone | |
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| Record name | PREDNISONE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3168 | |
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| Record name | Prednisone | |
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Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Q1: What is the primary mechanism of action of prednisone?
A1: Prednisone itself is a prodrug that is converted to its active metabolite, prednisolone, in the liver. Prednisolone acts by binding to the glucocorticoid receptor (GR) in the cytoplasm. [] This complex then translocates to the nucleus and influences gene expression, ultimately leading to a wide range of anti-inflammatory and immunosuppressive effects. []
Q2: How does prednisone differ from prednisolone in terms of activity?
A2: Prednisone is inactive until it is metabolized into prednisolone in the liver. [, ] Individuals lacking the necessary hepatic enzyme system may exhibit reduced clinical effects from prednisone. []
Q3: Can you elaborate on the immunosuppressive effects of prednisone?
A3: Prednisone, via prednisolone, exerts its immunosuppressive effects by modulating various immune cell functions. For instance, it inhibits interleukin 2 (IL-2) production and alters the ratio of helper T cells (OKT4+) to suppressor T cells (OKT8+). [] This modulation of cytokine production and immune cell populations contributes to its immunosuppressive properties. [, , ]
Q4: A study mentioned that prednisone slows the deterioration of muscle function in Duchenne Muscular Dystrophy (DMD). How does this effect relate to its primary mechanism of action?
A4: While the exact mechanism remains unclear, it's suggested that prednisone's anti-inflammatory properties might play a role in reducing muscle inflammation in DMD, thereby slowing down muscle fiber degeneration. []
Q5: What is the molecular formula and weight of prednisone?
A5: The molecular formula of prednisone is C21H26O5, and its molecular weight is 358.43 g/mol. [, ]
Q6: Are there any specific spectroscopic techniques used to characterize prednisone?
A6: Researchers utilize various techniques, including UV spectrophotometry, to characterize and quantify prednisone. [] For instance, UV spectrophotometry was employed to determine prednisone concentrations during the development of a biodegradable microsphere formulation. []
Q7: Has prednisone been formulated into a long-term controlled-release system?
A7: Yes, researchers have successfully developed prednisone-loaded biodegradable microspheres using poly(DL-lactide-co-glycolide) (PLGA) polymers. [] These microspheres demonstrate a suitable size and exhibit a long-term release profile. []
Q8: How is prednisone absorbed and distributed in the body?
A8: Prednisone is administered orally and absorbed from the gastrointestinal tract. [, ] It is then distributed to various tissues, though it does not readily cross the blood-brain barrier. []
Q9: How is prednisone metabolized and eliminated?
A9: Prednisone is primarily metabolized in the liver to its active form, prednisolone. [] Both prednisone and prednisolone undergo further metabolism, and the metabolites are primarily excreted in the urine. []
Q10: Does the route of administration affect prednisolone levels?
A10: Yes, intravenous administration of prednisolone phosphate results in significantly higher peak concentrations and area under the curve (AUC) compared to intravenous prednisolone phthalate or oral prednisone. []
Q11: Are there any known drug interactions that affect prednisone metabolism?
A11: Yes, rifampin, a drug known to induce hepatic enzymes, can accelerate prednisone metabolism, leading to decreased prednisone efficacy. [] In such cases, adjusting the prednisone dosage may be necessary to achieve the desired therapeutic effect. []
Q12: Can prednisone influence the pharmacokinetics of other drugs?
A12: While not directly addressed in the provided papers, prednisone's potential to induce or inhibit drug-metabolizing enzymes [] suggests a possibility of pharmacokinetic interactions with other drugs metabolized by the same enzymes.
Q13: What are the primary clinical applications of prednisone?
A13: Prednisone is used to treat various inflammatory and autoimmune diseases, including rheumatoid arthritis, [, , , ] nephrotic syndrome, [, ] giant cell arteritis, [, , , ] and idiopathic thrombocytopenic purpura (ITP). [, ]
Q14: Is prednisone effective in preventing recurrent focal glomerulosclerosis after a kidney transplant?
A14: A case study highlighted the importance of prednisone in maintaining remission of proteinuria in a patient with recurrent focal glomerulosclerosis after a kidney transplant. [] While the study suggests prednisone's potential, further research is needed to confirm its efficacy in preventing recurrence.
Q15: Are there any predictive factors for prednisone response in specific diseases?
A15: In infant acute lymphoblastic leukemia (ALL), prednisone response, defined by the degree of cytoreduction, is a strong predictor of treatment outcome. [] Patients with a good prednisone response have better event-free survival rates compared to poor responders. []
Q16: What are some known side effects associated with long-term prednisone use?
A16: Long-term prednisone use can lead to various adverse effects, including osteoporosis, [, ] cataracts, [] and an increased risk of infections. [, , ]
Q17: Does the dosage and duration of prednisone therapy affect the risk of side effects?
A17: Yes, higher doses and prolonged duration of prednisone therapy are associated with a higher risk of developing adverse effects. [, , , ]
Q18: Are there any novel drug delivery strategies being explored for prednisone?
A18: Researchers have explored biodegradable microsphere formulations using PLGA polymers for controlled and targeted delivery of prednisone. [] This approach aims to enhance drug efficacy and potentially minimize systemic side effects. [, ]
Q19: Have any biomarkers been identified to predict prednisone efficacy or monitor treatment response?
A19: A metabolomic study identified potential biomarkers in the serum of myasthenia gravis patients treated with prednisone. [] The study found changes in glycerophospholipids and arachidonic acid metabolites, suggesting their potential role as treatment response biomarkers. [, ]
Q20: Are there any environmental concerns related to prednisone?
A20: While not addressed in the provided papers, the widespread use of prednisone warrants investigation into its potential environmental impact and appropriate waste management strategies. []
Q21: Are there alternative treatments to prednisone?
A21: Yes, depending on the specific disease, several alternative treatments exist, including other immunosuppressants like cyclosporine, [, ] disease-modifying antirheumatic drugs (DMARDs) such as sulfasalazine and methotrexate, [, , ] and biological agents like tumor necrosis factor-alpha inhibitors and interleukin-1 receptor antagonists. [, , , ]
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