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 |
---|---|---|---|
Target ID: CHEMBL340 |
|||
Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB01222 |
1.32 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 |
|||
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 |
|||
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 |
|||
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 |
---|---|---|
Methodological aspects on clinical trials with inhaled corticosteroids: results of two comparisons between two steroid aerosols in patients with asthma. | 1982 |
|
Dysphonia caused by inhaled steroids: recognition of a characteristic laryngeal abnormality. | 1983 Nov |
|
Liver tumors in male rats following treatment with glucocorticosteroids. | 1992 |
|
Contact sensitivity and cross-reactivity of budesonide. | 1993 Apr |
|
Effects of glucocorticoids on lymphocyte activation in patients with steroid-sensitive and steroid-resistant asthma. | 1996 Dec |
|
Induction of the E-selectin promoter by interleukin 1 and tumour necrosis factor alpha, and inhibition by glucocorticoids. | 1997 Dec 1 |
|
The effects of inhaled glucocorticoids on bone mass and biochemical markers of bone homeostasis: a 1-year study of beclomethasone versus budesonide. | 1997 Jun |
|
[Steroid-induced myopathy in left-sided ulcerative colitis. Successful treatment and continued therapy with the topical steroid budesonide]. | 1997 Jun 15 |
|
Effects of several glucocorticosteroids and PDE4 inhibitors on increases in total lung eosinophil peroxidase (EPO) levels following either systemic or intratracheal administration in sephadex- or ovalbumin-induced inflammatory models. | 2000 Aug |
|
Transcriptional potencies of inhaled glucocorticoids. | 2000 Jul |
|
Evaluation of a clinical algorithm involving serum eosinophil cationic protein for guiding the anti-inflammatory treatment of bronchial asthma in childhood. | 2000 May |
|
Inhibition of GM-CSF secretion by topical corticosteroids and nedocromil sodium. A comparison study using nasal polyp epithelial cells. | 2000 May |
|
Comparison of hydrofluoroalkane-beclomethasone dipropionate Autohaler with budesonide Turbuhaler in asthma control. | 2001 |
|
A multicenter, randomized open study of early corticosteroid treatment (OSECT) in preterm infants with respiratory illness: comparison of early and late treatment and of dexamethasone and inhaled budesonide. | 2001 Feb |
|
Improved safety with equivalent asthma control in adults with chronic severe asthma on high-dose fluticasone propionate. | 2001 Sep |
|
Prevention of mouse lung tumors by budesonide and its modulation of biomarkers. | 2002 Jul |
|
Comparison of second controller medications in addition to inhaled corticosteroid in patients with moderate asthma. | 2002 May |
|
Budesonide-induced acute hepatitis in an HIV-positive patient with ritonavir as a co-medication. | 2002 May 24 |
|
The locally acting glucocorticosteroid budesonide enhances intestinal sugar uptake following intestinal resection in rats. | 2003 Feb |
|
In vivo and in vitro effects of SAR 943, a rapamycin analogue, on airway inflammation and remodeling. | 2003 Jan 15 |
|
Leukotriene modifier vs inhaled corticosteroid in mild-to-moderate asthma: clinical and anti-inflammatory effects. | 2004 May |
|
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine. | 2005 Aug |
|
Chemoprevention: mouse colon and lung tumor bioassay and modulation of DNA methylation as a biomarker. | 2005 Mar |
|
Effect of inhaled corticosteroid on an immunoreactive thymus and activation-regulated chemokine expression in the bronchial biopsies from asthmatics. | 2005 Mar |
|
Resveratrol, an extract of red wine, inhibits lipopolysaccharide induced airway neutrophilia and inflammatory mediators through an NF-kappaB-independent mechanism. | 2005 May |
|
The combined effects of zafirlukast, prednisone, and inhaled budesonide on IL-13 and IFN-gamma secretion. | 2005 Sep |
|
[Effects of beclomethasone dipropionate and budesonide on interleukin-13 induced cytokine release, proliferation and differentiation of the human lung fibroblasts]. | 2007 Aug |
|
Modulation by budesonide of DNA methylation and mRNA expression in mouse lung tumors. | 2007 Mar 1 |
|
The effect of corticosteroids on the disposal of long-acting beta2-agonists by airway smooth muscle cells. | 2007 Nov |
|
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008 Apr |
|
Oxidative stress modulates theophylline effects on steroid responsiveness. | 2008 Dec 19 |
|
Tolerance and rebound with zafirlukast in patients with persistent asthma. | 2008 May 19 |
|
A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions. | 2008 Oct |
|
Contact allergy to topical corticosteroids--results from the IVDK and epidemiological risk assessment. | 2009 Jan |
|
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010 Jul |
|
Rapid nongenomic actions of inhaled corticosteroids on long-acting β(2)-agonist transport in the airway. | 2011 Dec |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake. | 2011 Jun |
|
Hyalinization of the pyloric stomach in CD-1 mice following oral (dietary) administration of the corticosteroid agonists mometasone furoate, budesonide, and flunisolide. | 2011 Oct |
|
Contact sensitization in very young children. | 2011 Oct |
|
Design and synthesis of long acting inhaled corticosteroids for the treatment of asthma. | 2011 Oct 1 |
|
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 |
|
Budesonide/formoterol maintenance and reliever therapy in Asian patients (aged ≥16 years) with asthma: a sub-analysis of the COSMOS study. | 2012 Jul 1 |
|
Review article: a decision-making algorithm for the management of pregnancy in the inflammatory bowel disease patient. | 2012 Mar |
|
Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. | 2012 May 1 |
|
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). | 2013 Dec |
|
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 |
|
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
|
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 |
|
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).
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QR03BA02
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ATC |
R03BA02
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
FDA ORPHAN DRUG |
673818
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
VYLAER SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
FDA ORPHAN DRUG |
634418
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ATC |
R03AK07
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
FDA ORPHAN DRUG |
394613
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
FDA ORPHAN DRUG |
305710
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ATC |
R03AK12
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
NDF-RT |
N0000175576
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
DUORESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
25.1
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ATC |
D07AC09
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
FDA ORPHAN DRUG |
227406
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ATC |
A07EA06
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
LIVERTOX |
NBK548351
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
FDA ORPHAN DRUG |
670118
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-VATC |
QR01AD05
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
BIRESP ( AUTHORIZED: ASTHMA, PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
EU-Orphan Drug |
EU/3/13/1181
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
LABAZENIT (REFUSED: ASTHMA)
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
NDF-RT |
N0000175450
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
NCI_THESAURUS |
C521
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ATC |
R01AD05
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
28
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-VATC |
QR03AK07
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-VATC |
QA07EA06
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
BUDESONIDA (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
||
|
WHO-VATC |
QD07AC09
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB05955MIG
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
4145
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
Q3OKS62Q6X
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
C1027
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
Budesonide
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
5281004
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
257-139-7
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
DB01222
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
Q3OKS62Q6X
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
19831
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | RxNorm | ||
|
D019819
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
3207
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
7434
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
1078201
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
419
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
51333-22-3
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
m2746
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | Merck Index | ||
|
757788
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
DTXSID8020202
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
BUDESONIDE
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY | |||
|
CHEMBL1370
Created by
admin on Sat Dec 16 15:43:08 GMT 2023 , Edited by admin on Sat Dec 16 15:43:08 GMT 2023
|
PRIMARY |
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
PRODRUG (METABOLITE ACTIVE)
SUBSTANCE RECORD