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 Date9.6569282E11 |
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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 Date1.35812166E12 |
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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 Date1.42698244E12 |
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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 Date1.00189438E12 |
PubMed
Title | Date | PubMed |
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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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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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Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids. | 1995 Jan |
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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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Deteriorating diabetic control associated with high-dose inhaled budesonide. | 1999 Jul |
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Delayed generalized allergic reactions to corticosteroids. | 2000 |
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Transcriptional potencies of inhaled glucocorticoids. | 2000 Jul |
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Comparison of hydrofluoroalkane-beclomethasone dipropionate Autohaler with budesonide Turbuhaler in asthma control. | 2001 |
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Prevention of mouse lung tumors by budesonide and its modulation of biomarkers. | 2002 Jul |
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Inhibition of chemokine production from human airway smooth muscle cells by fluticasone, budesonide and beclomethasone. | 2004 |
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Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine. | 2005 Aug |
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The effect of intranasal steroid budesonide on the congestion-related sleep disturbance and daytime somnolence in patients with perennial allergic rhinitis. | 2005 Jul-Aug |
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Resveratrol, an extract of red wine, inhibits lipopolysaccharide induced airway neutrophilia and inflammatory mediators through an NF-kappaB-independent mechanism. | 2005 May |
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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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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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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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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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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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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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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 |
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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admin on Thu Jul 06 21:16:01 UTC 2023 , Edited by admin on Thu Jul 06 21:16:01 UTC 2023
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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
Created by
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WHO-VATC |
QR01AD05
Created by
admin on Thu Jul 06 21:16:01 UTC 2023 , Edited by admin on Thu Jul 06 21:16:01 UTC 2023
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EMA ASSESSMENT REPORTS |
BIRESP ( AUTHORIZED: ASTHMA, PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
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admin on Thu Jul 06 21:16:01 UTC 2023 , Edited by admin on Thu Jul 06 21:16:01 UTC 2023
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EU-Orphan Drug |
EU/3/13/1181
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admin on Thu Jul 06 21:16:01 UTC 2023 , Edited by admin on Thu Jul 06 21:16:01 UTC 2023
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EMA ASSESSMENT REPORTS |
LABAZENIT (REFUSED: ASTHMA)
Created by
admin on Thu Jul 06 21:16:01 UTC 2023 , Edited by admin on Thu Jul 06 21:16:01 UTC 2023
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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
Created by
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WHO-VATC |
QA07EA06
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admin on Thu Jul 06 21:16:01 UTC 2023 , Edited by admin on Thu Jul 06 21:16:01 UTC 2023
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EMA ASSESSMENT REPORTS |
BUDESONIDA (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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admin on Thu Jul 06 21:16:01 UTC 2023 , Edited by admin on Thu Jul 06 21:16:01 UTC 2023
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WHO-VATC |
QD07AC09
Created by
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Code System | Code | Type | Description | ||
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SUB05955MIG
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4145
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Q3OKS62Q6X
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PRIMARY | |||
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C1027
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PRIMARY | |||
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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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PRIMARY | |||
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M2746
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PRIMARY | Merck Index | ||
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757788
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DTXSID8020202
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BUDESONIDE
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CHEMBL1370
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PRIMARY |
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