Details
Stereochemistry | EPIMERIC |
Molecular Formula | C25H34O6 |
Molecular Weight | 430.5339 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(CCC)O2)C(=O)CO
InChI
InChIKey=VOVIALXJUBGFJZ-KWVAZRHASA-N
InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01222
https://www.drugs.com/cdi/budesonide-extended-release-tablets.html
http://www.wikidoc.org/index.php/Budesonide_(inhalation)#Adverse_Reactions
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01222
https://www.drugs.com/cdi/budesonide-extended-release-tablets.html
http://www.wikidoc.org/index.php/Budesonide_(inhalation)#Adverse_Reactions
Budesonide is a glucocorticoid used in the management of asthma, the treatment of various skin disorders, allergic rhinitis and ulcerative colitis. The precise mechanism of corticosteroid actions on inflammation in asthma is not well known. Inflammation is an important component in the pathogenesis of asthma. Corticosteroids have been shown to have a wide range of inhibitory activities against multiple cell types (e.g., mast cells, eosinophils, neutrophils, macrophages, and lymphocytes) and mediators (e.g., histamine, eicosanoids, leukotrienes, and cytokines) involved in allergic- and non-allergic-mediated inflammation. The anti-inflammatory actions of corticosteroids may contribute to their efficacy in asthma. Commonly reported side effects of budesonide include: acne vulgaris, moon face, and bruise. Other side effects include: ankle edema, hirsutism, weakness, arthralgia, nausea, and rhinitis. Ketoconazole, a potent inhibitor of cytochrome P450 (CYP) isoenzyme 3A4 (CYP3A4), the main metabolic enzyme for corticosteroids, increased plasma levels of orally ingested budesonide.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3811967
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL340 |
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Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB01222 |
1.32 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | PULMICORT RESPULES Approved UsePULMICORT FLEXHALER is a corticosteroid indicated for: • Maintenance treatment of asthma as prophylactic therapy in adult and pediatric patients six years of age or older. (1.1) Important Limitations: • Not indicated for the relief of acute bronchospasm. (1.1) 1.1 Treatment of Asthma PULMICORT FLEXHALER is indicated for the maintenance treatment of asthma as prophylactic therapy in patients six years of age or older. Important Limitations of Use: PULMICORT FLEXHALER is NOT indicated for the relief of acute bronchospasm. Launch Date2000 |
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Primary | UCERIS Approved UseUCERIS rectal foam is indicated for the induction of remission in patients with active mild to moderate distal ulcerative colitis extending up to 40 cm from the anal verge. Launch Date2013 |
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Palliative | RHINOCORT ALLERGY Approved UseIt is indicated for the treatment of nasal symptoms of seasonal or perennial allergic rhinitis in adults and children Launch Date2015 |
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Primary | ENTOCORT EC Approved UseENTOCORT EC is indicated for the treatment of mild to moderate active Crohn's disease involving the ileum and/or the ascending colon. Launch Date2001 |
PubMed
Title | Date | PubMed |
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Methodological aspects on clinical trials with inhaled corticosteroids: results of two comparisons between two steroid aerosols in patients with asthma. | 1982 |
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Dysphonia caused by inhaled steroids: recognition of a characteristic laryngeal abnormality. | 1983 Nov |
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Contact sensitivity and cross-reactivity of budesonide. | 1993 Apr |
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[Contact allergy to topical glucocorticoids]. | 1993 Feb |
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Contact allergies to topical corticosteroids. | 1993 Mar |
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The effect of different corticosteroids and cyclosporin A on interleukin-4 and interleukin-5 release from murine TH2-type T cells. | 1994 Aug 1 |
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Frequency of voice problems and cough in patients using pressurized aerosol inhaled steroid preparations. | 1995 Apr |
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Effect of terfenadine and budesonide on nasal symptoms, olfaction, and nasal airway patency following allergen challenge. | 1995 Aug |
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Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids. | 1995 Jan |
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Evaluation of the inhibitory effects of budesonide on the mitogen-induced or the allergen-induced activation of blood mononuclear cells isolated from asthmatic patients. | 1995 Jul |
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Effects of glucocorticoids on lymphocyte activation in patients with steroid-sensitive and steroid-resistant asthma. | 1996 Dec |
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Induction of the E-selectin promoter by interleukin 1 and tumour necrosis factor alpha, and inhibition by glucocorticoids. | 1997 Dec 1 |
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The effects of inhaled glucocorticoids on bone mass and biochemical markers of bone homeostasis: a 1-year study of beclomethasone versus budesonide. | 1997 Jun |
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[Steroid-induced myopathy in left-sided ulcerative colitis. Successful treatment and continued therapy with the topical steroid budesonide]. | 1997 Jun 15 |
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Severe hypokalemia after budesonide treatment for Crohn's disease. | 1997 Mar |
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Reversible dementia with parkinsonian features associated with budesonide use. | 2006 Aug 22 |
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Prevention of mouse lung tumors and modulation of DNA methylation by combined treatment with budesonide and R115777 (ZarnestraMT). | 2006 Dec |
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[Effects of beclomethasone dipropionate and budesonide on interleukin-13 induced cytokine release, proliferation and differentiation of the human lung fibroblasts]. | 2007 Aug |
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Modulation by budesonide of DNA methylation and mRNA expression in mouse lung tumors. | 2007 Mar 1 |
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The effect of corticosteroids on the disposal of long-acting beta2-agonists by airway smooth muscle cells. | 2007 Nov |
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Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008 Apr |
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Oxidative stress modulates theophylline effects on steroid responsiveness. | 2008 Dec 19 |
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Tolerance and rebound with zafirlukast in patients with persistent asthma. | 2008 May 19 |
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A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions. | 2008 Oct |
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Mass casualties from acute inhalation of chlorine gas. | 2009 Dec |
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Thirteen-year follow-up of early intervention with an inhaled corticosteroid in patients with asthma. | 2009 Dec |
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Management of Crohn's disease in adults. | 2009 Feb |
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Contact allergy to topical corticosteroids--results from the IVDK and epidemiological risk assessment. | 2009 Jan |
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Expression and regulation of the bile acid transporter, OSTalpha-OSTbeta in rat and human intestine and liver. | 2009 Jul |
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Budesonide prevents cytokine-induced decrease of the relaxant responses to formoterol and terbutaline, but not to salmeterol, in mouse trachea. | 2010 Apr |
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Recurrent spontaneous gastrointestinal graft-versus-host disease in autologous hematopoietic stem cell transplantation. | 2010 Feb |
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Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010 Jul |
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Rapid nongenomic actions of inhaled corticosteroids on long-acting β(2)-agonist transport in the airway. | 2011 Dec |
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The role of lithocholic acid in the regulation of bile acid detoxication, synthesis, and transport proteins in rat and human intestine and liver slices. | 2011 Feb |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake. | 2011 Jun |
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Activities of aldo-keto reductase 1 enzymes on two inhaled corticosteroids: implications for the pharmacological effects of inhaled corticosteroids. | 2011 May 30 |
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Hyalinization of the pyloric stomach in CD-1 mice following oral (dietary) administration of the corticosteroid agonists mometasone furoate, budesonide, and flunisolide. | 2011 Oct |
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Contact sensitization in very young children. | 2011 Oct |
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Design and synthesis of long acting inhaled corticosteroids for the treatment of asthma. | 2011 Oct 1 |
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Some OH-PCBs are more potent inhibitors of aromatase activity and (anti-) glucocorticoids than non-dioxin like (NDL)-PCBs and MeSO₂-PCBs. | 2011 Oct 10 |
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Budesonide/formoterol maintenance and reliever therapy in Asian patients (aged ≥16 years) with asthma: a sub-analysis of the COSMOS study. | 2012 Jul 1 |
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Review article: a decision-making algorithm for the management of pregnancy in the inflammatory bowel disease patient. | 2012 Mar |
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Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. | 2012 May 1 |
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Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). | 2013 Dec |
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Mechanisms of action of hormone-sensitive lipase in mouse Leydig cells: its role in the regulation of the steroidogenic acute regulatory protein. | 2013 Mar 22 |
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Potentiated interaction between ineffective doses of budesonide and formoterol to control the inhaled cadmium-induced up-regulation of metalloproteinases and acute pulmonary inflammation in rats. | 2014 |
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Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
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Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs. | 2015 Jun |
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Thiobenzothiazole-modified Hydrocortisones Display Anti-inflammatory Activity with Reduced Impact on Islet β-Cell Function. | 2015 May 22 |
Sample Use Guides
200 to 400 ug twice daily. If previous therapy was Oral Corticosteroids - 400 to 800 ug twice daily rectal foam: 1 metered dose administered twice daily for 2 weeks followed by 1 metered dose (rectal foam contains 2 mg budesonide per metered dose). Administered once daily for 4 weeks.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9374115
Increased hemopoietic activity in naive bone marrow, stimulated by serum obtained 24 h after allergen inhalation from sensitized dogs, can be prevented by prior incubation of the marrow with budesonide (10−7 M).
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QR03BA02
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WHO-ATC |
R03BA02
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FDA ORPHAN DRUG |
673818
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EMA ASSESSMENT REPORTS |
VYLAER SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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FDA ORPHAN DRUG |
634418
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WHO-ATC |
R03AK07
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FDA ORPHAN DRUG |
394613
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FDA ORPHAN DRUG |
305710
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WHO-ATC |
R03AK12
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NDF-RT |
N0000175576
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EMA ASSESSMENT REPORTS |
DUORESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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WHO-ESSENTIAL MEDICINES LIST |
25.1
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WHO-ATC |
D07AC09
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FDA ORPHAN DRUG |
227406
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WHO-ATC |
A07EA06
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LIVERTOX |
NBK548351
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FDA ORPHAN DRUG |
670118
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WHO-VATC |
QR01AD05
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EMA ASSESSMENT REPORTS |
BIRESP ( AUTHORIZED: ASTHMA, PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
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EU-Orphan Drug |
EU/3/13/1181
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EMA ASSESSMENT REPORTS |
LABAZENIT (REFUSED: ASTHMA)
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NDF-RT |
N0000175450
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NCI_THESAURUS |
C521
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WHO-ATC |
R01AD05
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WHO-ESSENTIAL MEDICINES LIST |
28
Created by
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WHO-VATC |
QR03AK07
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WHO-VATC |
QA07EA06
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EMA ASSESSMENT REPORTS |
BUDESONIDA (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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WHO-VATC |
QD07AC09
Created by
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SUB05955MIG
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4145
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Q3OKS62Q6X
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C1027
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Budesonide
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5281004
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257-139-7
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DB01222
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Q3OKS62Q6X
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19831
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D019819
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3207
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7434
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1078201
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419
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51333-22-3
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m2746
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757788
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DTXSID8020202
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BUDESONIDE
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CHEMBL1370
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