Prednisone
Vue d'ensemble
Description
La prednisone est un glucocorticoïde synthétique principalement utilisé pour ses propriétés anti-inflammatoires et immunosuppressives . Il s'agit d'un promédicament qui est métabolisé dans le foie en sa forme active, la prednisolone . La this compound est largement utilisée dans le traitement de diverses affections telles que l'asthme, la bronchopneumopathie chronique obstructive, les maladies rhumatismales et certains types de cancer .
Mécanisme D'action
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
This compound 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
This compound has a bioavailability of 70% . It is metabolized in the liver to its active form, prednisolone . The elimination half-life of this compound is 2 to 3 hours in adults . This compound is excreted in the urine as conjugates . The time to peak for oral this compound is 2 hours for immediate-release tablets and 6 to 6.5 hours for delayed-release tablets .
Result of Action
The result of this compound’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 this compound 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 this compound 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 this compound to prednisolone may be impaired in patients with liver disease . Therefore, the action, efficacy, and stability of this compound can be influenced by the patient’s health status and age, among other factors.
Applications De Recherche Scientifique
Prednisone has a wide range of applications in scientific research:
Analyse Biochimique
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
This compound 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
This compound exerts its effects at the molecular level through binding interactions with biomolecules and changes in gene expression. This compound 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 this compound change over time in laboratory settings. For example, a study showed that even short-term, low dosage use of this compound 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 this compound vary with different dosages in animal models. A study on dogs showed that this compound concentrations in various tissues were increased or decreased depending on the dosage and the specific tissue .
Metabolic Pathways
This compound 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
This compound is transported and distributed within cells and tissues. A study showed that the tissue distribution of this compound and prednisolone was affected by certain factors, leading to increased or decreased concentrations in various tissues .
Subcellular Localization
The subcellular localization of this compound and its effects on its activity or function are complex. This compound 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 .
Méthodes De Préparation
Voies synthétiques et conditions réactionnelles : La préparation de la prednisone implique généralement plusieurs étapes à partir d'un oxyde de moisissure. Le procédé comprend une réaction d'oxydation de Platts, suivie d'une réaction d'addition de brome, d'un retrait de brome et d'une réaction d'addition d'iode en 21 bits . La dernière étape implique une réaction de remplacement en 21 bits pour obtenir de la this compound .
Méthodes de production industrielle : La production industrielle de this compound implique souvent l'utilisation d'acétate d'hydrocortisone comme matière première . Le processus comprend des étapes telles que l'oxydation, la réduction et l'estérification pour produire de la this compound à grande échelle . Les méthodes sont conçues pour minimiser les déchets et réduire l'impact environnemental en recyclant le chrome et l'acide acétique .
Analyse Des Réactions Chimiques
Types de réactions : La prednisone subit diverses réactions chimiques, notamment l'oxydation, la réduction et la substitution .
Réactifs et conditions courants :
Oxydation : Réaction d'oxydation de Platts utilisant de l'oxyde de moisissure.
Substitution : Les réactions d'addition et de retrait du brome sont courantes dans la synthèse de la this compound.
Produits majeurs : Le principal produit formé par ces réactions est la this compound elle-même, qui est ensuite transformée en sa forme active, la prednisolone .
4. Applications de la recherche scientifique
La this compound a un large éventail d'applications dans la recherche scientifique :
Chimie : Utilisé comme composé de référence dans l'étude des glucocorticoïdes et de leurs dérivés.
Biologie : Étudié pour ses effets sur les processus cellulaires et l'expression des gènes.
5. Mécanisme d'action
La this compound exerce ses effets en étant convertie en prednisolone dans le foie . La prednisolone se lie ensuite aux récepteurs des glucocorticoïdes, les activant et déclenchant des changements dans l'expression des gènes . Cela conduit à la suppression de la migration des leucocytes polymorphonucléaires et à l'inversion de l'augmentation de la perméabilité capillaire, réduisant ainsi l'inflammation . Il supprime également le système immunitaire en réduisant l'activité et le volume du système immunitaire .
Composés similaires :
- Dexaméthasone
- Méthotrexate
- Mycophénolate
- Mercaptopurine
- Azathioprine
- Leflunomide
Comparaison : La this compound est unique en son genre en ce qu'elle peut être convertie en une forme active, la prednisolone, qui a de puissants effets anti-inflammatoires et immunosuppresseurs . Comparée à la dexaméthasone, la this compound a une demi-vie plus courte et est moins puissante . Le méthotrexate et le mycophénolate sont principalement utilisés comme immunosuppresseurs, mais n'ont pas les mêmes propriétés anti-inflammatoires que la this compound . La mercaptopurine, l'azathioprine et le leflunomide sont également utilisés comme immunosuppresseurs, mais ils ont des mécanismes d'action différents et sont utilisés dans des contextes cliniques différents .
Comparaison Avec Des Composés Similaires
- 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, this compound 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 this compound . Mercaptopurine, azathioprine, and leflunomide are also used as immunosuppressants but have different mechanisms of action and are used in different clinical contexts .
Propriétés
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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| 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. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Prednisone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00635 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PREDNISONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
| 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. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PREDNISONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Prednisone | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=53-03-2 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Prednisone [USP:INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000053032 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Prednisone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00635 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | prednisone | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=10023 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | Pregna-1,4-diene-3,11,20-trione, 17,21-dihydroxy- | |
| Source | EPA Chemicals under the TSCA | |
| URL | https://www.epa.gov/chemicals-under-tsca | |
| Description | EPA Chemicals under the Toxic Substances Control Act (TSCA) collection contains information on chemicals and their regulations under TSCA, including non-confidential content from the TSCA Chemical Substance Inventory and Chemical Data Reporting. | |
| 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. | |
| Record name | Prednisone | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.000.147 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | PREDNISONE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/VB0R961HZT | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | PREDNISONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
| 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. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Prednisone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00635 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PREDNISONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
| 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. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
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: this compound 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 this compound differ from prednisolone in terms of activity?
A2: this compound is inactive until it is metabolized into prednisolone in the liver. [, ] Individuals lacking the necessary hepatic enzyme system may exhibit reduced clinical effects from this compound. []
Q3: Can you elaborate on the immunosuppressive effects of this compound?
A3: this compound, 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 this compound 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 this compound'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 this compound?
A5: The molecular formula of this compound is C21H26O5, and its molecular weight is 358.43 g/mol. [, ]
Q6: Are there any specific spectroscopic techniques used to characterize this compound?
A6: Researchers utilize various techniques, including UV spectrophotometry, to characterize and quantify this compound. [] For instance, UV spectrophotometry was employed to determine this compound concentrations during the development of a biodegradable microsphere formulation. []
Q7: Has this compound been formulated into a long-term controlled-release system?
A7: Yes, researchers have successfully developed this compound-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 this compound absorbed and distributed in the body?
A8: this compound 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 this compound metabolized and eliminated?
A9: this compound is primarily metabolized in the liver to its active form, prednisolone. [] Both this compound 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 this compound. []
Q11: Are there any known drug interactions that affect this compound metabolism?
A11: Yes, rifampin, a drug known to induce hepatic enzymes, can accelerate this compound metabolism, leading to decreased this compound efficacy. [] In such cases, adjusting the this compound dosage may be necessary to achieve the desired therapeutic effect. []
Q12: Can this compound influence the pharmacokinetics of other drugs?
A12: While not directly addressed in the provided papers, this compound'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 this compound?
A13: this compound is used to treat various inflammatory and autoimmune diseases, including rheumatoid arthritis, [, , , ] nephrotic syndrome, [, ] giant cell arteritis, [, , , ] and idiopathic thrombocytopenic purpura (ITP). [, ]
Q14: Is this compound effective in preventing recurrent focal glomerulosclerosis after a kidney transplant?
A14: A case study highlighted the importance of this compound in maintaining remission of proteinuria in a patient with recurrent focal glomerulosclerosis after a kidney transplant. [] While the study suggests this compound's potential, further research is needed to confirm its efficacy in preventing recurrence.
Q15: Are there any predictive factors for this compound response in specific diseases?
A15: In infant acute lymphoblastic leukemia (ALL), this compound response, defined by the degree of cytoreduction, is a strong predictor of treatment outcome. [] Patients with a good this compound response have better event-free survival rates compared to poor responders. []
Q16: What are some known side effects associated with long-term this compound use?
A16: Long-term this compound use can lead to various adverse effects, including osteoporosis, [, ] cataracts, [] and an increased risk of infections. [, , ]
Q17: Does the dosage and duration of this compound therapy affect the risk of side effects?
A17: Yes, higher doses and prolonged duration of this compound therapy are associated with a higher risk of developing adverse effects. [, , , ]
Q18: Are there any novel drug delivery strategies being explored for this compound?
A18: Researchers have explored biodegradable microsphere formulations using PLGA polymers for controlled and targeted delivery of this compound. [] This approach aims to enhance drug efficacy and potentially minimize systemic side effects. [, ]
Q19: Have any biomarkers been identified to predict this compound efficacy or monitor treatment response?
A19: A metabolomic study identified potential biomarkers in the serum of myasthenia gravis patients treated with this compound. [] 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 this compound?
A20: While not addressed in the provided papers, the widespread use of this compound warrants investigation into its potential environmental impact and appropriate waste management strategies. []
Q21: Are there alternative treatments to this compound?
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. [, , , ]
Avertissement et informations sur les produits de recherche in vitro
Veuillez noter que tous les articles et informations sur les produits présentés sur BenchChem sont destinés uniquement à des fins informatives. Les produits disponibles à l'achat sur BenchChem sont spécifiquement conçus pour des études in vitro, qui sont réalisées en dehors des organismes vivants. Les études in vitro, dérivées du terme latin "in verre", impliquent des expériences réalisées dans des environnements de laboratoire contrôlés à l'aide de cellules ou de tissus. Il est important de noter que ces produits ne sont pas classés comme médicaments et n'ont pas reçu l'approbation de la FDA pour la prévention, le traitement ou la guérison de toute condition médicale, affection ou maladie. Nous devons souligner que toute forme d'introduction corporelle de ces produits chez les humains ou les animaux est strictement interdite par la loi. Il est essentiel de respecter ces directives pour assurer la conformité aux normes légales et éthiques en matière de recherche et d'expérimentation.
![butane-1,4-diol;1-isocyanato-4-[(4-isocyanatophenyl)methyl]benzene](/img/structure/B1678996.png)
