Details
Stereochemistry | EPIMERIC |
Molecular Formula | C25H34O6 |
Molecular Weight | 430.5348 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC1([H])O[C@]2([H])C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@]([H])(C[C@]3(C)[C@]2(C(=O)CO)O1)O
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
Molecular Formula | C25H34O6 |
Molecular Weight | 430.5348 |
Charge | 0 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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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 |
---|---|---|---|---|
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 |
---|---|---|
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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Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids. | 1995 Jan |
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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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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 |
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Effects of topical glucocorticoids on in vitro lactoferrin glandular secretion: comparison between human upper and lower airways. | 2000 Dec |
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Transcriptional potencies of inhaled glucocorticoids. | 2000 Jul |
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Inhibition of GM-CSF secretion by topical corticosteroids and nedocromil sodium. A comparison study using nasal polyp epithelial cells. | 2000 May |
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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 |
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Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis. | 2001 Nov 23 |
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Budesonide-induced acute hepatitis in an HIV-positive patient with ritonavir as a co-medication. | 2002 May 24 |
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The locally acting glucocorticosteroid budesonide enhances intestinal sugar uptake following intestinal resection in rats. | 2003 Feb |
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Stimulating effect of glucocorticosteroids on intestinal fructose transport in rats is increased by feeding a saturated fatty acid diet. | 2003 Nov |
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Neuropsychologic changes and inhaled corticosteroids. | 2004 Aug |
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Comparison of in vitro-activity of commonly used topical glucocorticoids on cytokine- and phospholipase inhibition. | 2004 Aug 31 |
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Effects of different anti-asthmatic agents on induced sputum and eosinophil cationic protein in mild asthmatics. | 2004 Nov |
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Generalized seizure in a Mauritian woman taking bupropion. | 2004 Oct |
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A randomized phase IIb trial of pulmicort turbuhaler (budesonide) in people with dysplasia of the bronchial epithelium. | 2004 Oct 1 |
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Transactivation via the human glucocorticoid and mineralocorticoid receptor by therapeutically used steroids in CV-1 cells: a comparison of their glucocorticoid and mineralocorticoid properties. | 2004 Sep |
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Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine. | 2005 Aug |
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Novel sulfhydryl-reactive compounds orazipone and OR-1958 inhibit cytokine production and histamine release in rat and human mast cells. | 2005 Jan |
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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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Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. | 2006 Mar |
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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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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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Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake. | 2011 Jun |
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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 |
|
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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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 |
|
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:05:48 UTC 2021
by
admin
on
Fri Jun 25 21:05:48 UTC 2021
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Record UNII |
Q3OKS62Q6X
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
---|---|---|---|---|
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WHO-VATC |
QR03BA02
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-ATC |
R03BA02
Created by
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FDA ORPHAN DRUG |
305710
Created by
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FDA ORPHAN DRUG |
673818
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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EMA ASSESSMENT REPORTS |
VYLAER SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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FDA ORPHAN DRUG |
634418
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-ATC |
R03AK07
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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FDA ORPHAN DRUG |
394613
Created by
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WHO-ATC |
R03AK12
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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NDF-RT |
N0000175576
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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EMA ASSESSMENT REPORTS |
DUORESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-ESSENTIAL MEDICINES LIST |
25.1
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-ATC |
D07AC09
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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FDA ORPHAN DRUG |
227406
Created by
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WHO-ATC |
A07EA06
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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LIVERTOX |
125
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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FDA ORPHAN DRUG |
670118
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-VATC |
QR01AD05
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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EMA ASSESSMENT REPORTS |
BIRESP ( AUTHORIZED: ASTHMA, PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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EU-Orphan Drug |
EU/3/13/1181
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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EMA ASSESSMENT REPORTS |
LABAZENIT (REFUSED: ASTHMA)
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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NDF-RT |
N0000175450
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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NCI_THESAURUS |
C521
Created by
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WHO-ATC |
R01AD05
Created by
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WHO-ESSENTIAL MEDICINES LIST |
28
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-VATC |
QR03AK07
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-VATC |
QA07EA06
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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EMA ASSESSMENT REPORTS |
BUDESONIDA (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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WHO-VATC |
QD07AC09
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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Code System | Code | Type | Description | ||
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SUB05955MIG
Created by
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PRIMARY | |||
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4145
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | |||
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C1027
Created by
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PRIMARY | |||
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Budesonide
Created by
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PRIMARY | |||
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5281004
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | |||
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257-139-7
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | |||
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DB01222
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | |||
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Q3OKS62Q6X
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | |||
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19831
Created by
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PRIMARY | RxNorm | ||
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D019819
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PRIMARY | |||
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7434
Created by
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PRIMARY | |||
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419
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | |||
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51333-22-3
Created by
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PRIMARY | |||
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1078201
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | USP-RS | ||
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M2746
Created by
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PRIMARY | Merck Index | ||
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51333-22-3
Created by
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PRIMARY | |||
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BUDESONIDE
Created by
admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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PRIMARY | |||
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CHEMBL1370
Created by
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PRIMARY |
Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
No unchanged budesonide is detected in urine.
URINE
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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BINDER->LIGAND |
Plasma protein binding is estimated to be 85 to 90% in the concentration range 1 to 230 nmol/L, independent of gender.
BINDING
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
In vitro mediator: CYP3A4
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METABOLITE -> PARENT |
Catalyzed by two enzymes, the 4-ene-5.BETA.-reductase and the 4-ene-5.ALPHA.-reductase
MINOR
URINE
|
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METABOLITE -> PARENT |
In vitro mediator: CYP3A4
|
||
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METABOLITE -> PARENT |
MINOR
URINE
|
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METABOLITE -> PARENT |
MINOR
URINE
|
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|
METABOLITE -> PARENT |
MINOR
URINE
|
||
|
METABOLITE -> PARENT |
MINOR
URINE
|
||
|
METABOLITE -> PARENT |
MINOR
URINE
|
||
|
METABOLITE -> PARENT |
MINOR
URINE
|
||
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METABOLITE -> PARENT |
MINOR
URINE
|
||
|
METABOLITE -> PARENT |
MINOR
URINE
|
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METABOLITE -> PARENT |
MAJOR
URINE
|
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METABOLITE -> PARENT |
MINOR
URINE
|
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METABOLITE -> PARENT |
MINOR
URINE
|
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|
METABOLITE -> PARENT |
MINOR
URINE
|
||
|
METABOLITE -> PARENT |
Catalyzed by two enzymes, the 4-ene-5.BETA.-reductase and the 4-ene-5.ALPHA.-reductase
MINOR
URINE
|
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METABOLITE -> PARENT |
MINOR
URINE
|
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METABOLITE -> PARENT |
Catalyzed by two enzymes, the 4-ene-5.BETA.-reductase and the 4-ene-5.ALPHA.-reductase. The second stage utilizes the enzymes 3.ALPHA.- and, to a much lesser extent, 3.BETA.-hydroxysteroid dehydrogenases
MINOR
URINE
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Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
Limit includes both epimers
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Limit includes both epimers
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
This impurity is to be reported under total unspecified impurities. Do not report it under total specified impurities.
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Limit includes both epimers
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|