U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of BUDESONIDE

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

HIDE SMILES / InChI

Description
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

Curator's Comment:: Known to be CNS penetrant in mouse. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.32 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PULMICORT RESPULES

Approved Use

PULMICORT 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 Date

9.6569282E11
Primary
UCERIS

Approved Use

UCERIS 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 Date

1.35812166E12
Palliative
RHINOCORT ALLERGY

Approved Use

It is indicated for the treatment of nasal symptoms of seasonal or perennial allergic rhinitis in adults and children

Launch Date

1.42698244E12
Primary
ENTOCORT EC

Approved Use

ENTOCORT EC is indicated for the treatment of mild to moderate active Crohn's disease involving the ileum and/or the ascending colon.

Launch Date

1.00189438E12
PubMed

PubMed

TitleDatePubMed
Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids.
1995 Jan
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
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
Severe hypokalemia after budesonide treatment for Crohn's disease.
1997 Mar
Deteriorating diabetic control associated with high-dose inhaled budesonide.
1999 Jul
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase.
1999 Sep
Delayed generalized allergic reactions to corticosteroids.
2000
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
A study comparing the clinical pharmacokinetics, pharmacodynamics, and tolerability of triamcinolone acetonide HFA-134a metered-dose inhaler and budesonide dry-powder inhaler following inhalation administration.
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
Apoptosis of airway epithelial cells induced by corticosteroids.
2001 Nov 15
Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis.
2001 Nov 23
Comparison of second controller medications in addition to inhaled corticosteroid in patients with moderate asthma.
2002 May
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
Neuropsychologic changes and inhaled corticosteroids.
2004 Aug
Comparison of in vitro-activity of commonly used topical glucocorticoids on cytokine- and phospholipase inhibition.
2004 Aug 31
The effects of add-on zafirlukast treatment to budesonide on bronchial hyperresponsiveness and serum levels of eosinophilic cationic protein and total antioxidant capacity in asthmatic patients.
2004 Dec
Leukotriene modifier vs inhaled corticosteroid in mild-to-moderate asthma: clinical and anti-inflammatory effects.
2004 May
Effects of different anti-asthmatic agents on induced sputum and eosinophil cationic protein in mild asthmatics.
2004 Nov
Novel sulfhydryl-reactive compounds orazipone and OR-1958 inhibit cytokine production and histamine release in rat and human mast cells.
2005 Jan
The effect of intranasal steroid budesonide on the congestion-related sleep disturbance and daytime somnolence in patients with perennial allergic rhinitis.
2005 Jul-Aug
Chemoprevention: mouse colon and lung tumor bioassay and modulation of DNA methylation as a biomarker.
2005 Mar
The combined effects of zafirlukast, prednisone, and inhaled budesonide on IL-13 and IFN-gamma secretion.
2005 Sep
Reversible dementia with parkinsonian features associated with budesonide use.
2006 Aug 22
Prevention of mouse lung tumors and modulation of DNA methylation by combined treatment with budesonide and R115777 (ZarnestraMT).
2006 Dec
Modulation by budesonide of DNA methylation and mRNA expression in mouse lung tumors.
2007 Mar 1
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
A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions.
2008 Oct
Mass casualties from acute inhalation of chlorine gas.
2009 Dec
Contact allergy to topical corticosteroids--results from the IVDK and epidemiological risk assessment.
2009 Jan
Budesonide prevents cytokine-induced decrease of the relaxant responses to formoterol and terbutaline, but not to salmeterol, in mouse trachea.
2010 Apr
Recurrent spontaneous gastrointestinal graft-versus-host disease in autologous hematopoietic stem cell transplantation.
2010 Feb
Rapid nongenomic actions of inhaled corticosteroids on long-acting β(2)-agonist transport in the airway.
2011 Dec
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
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Hyalinization of the pyloric stomach in CD-1 mice following oral (dietary) administration of the corticosteroid agonists mometasone furoate, budesonide, and flunisolide.
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
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
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
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
Patents

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
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
BUDESONIDE
EP   INN   JAN   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
BREZTRI COMPONENT BUDESONIDE
Brand Name English
ORTIKOS
Brand Name English
BUDESONIDE [USAN]
Common Name English
UCERIS COMPONENT BUDESONIDE
Brand Name English
BUDESONIDE COMPONENT OF UCERIS
Brand Name English
ENTOCORT
Brand Name English
S-1320
Code English
BUDESONIDE [VANDF]
Common Name English
RHINOCORT
Brand Name English
BUDESONIDE [EP MONOGRAPH]
Common Name English
PULMICORT
Brand Name English
BUDESONIDE [MI]
Common Name English
R01AD05
Code English
BUDESONIDE [WHO-DD]
Common Name English
BUDESONIDE [INN]
Common Name English
BUDESONIDE COMPONENT OF SYMBICORT
Common Name English
BUDESONIDE COMPONENT OF BREZTRI
Brand Name English
SYMBICORT COMPONENT BUDESONIDE
Common Name English
UCERIS
Brand Name English
MAP-0010
Code English
BUDESONIDE [ORANGE BOOK]
Common Name English
NSC-757788
Code English
BUDESONIDE [USP MONOGRAPH]
Common Name English
MAP0010
Code English
BUDESONIDE [USP-RS]
Common Name English
BUDESONIDE [JAN]
Common Name English
ENTOCORT EC
Brand Name English
(RS)-11.BETA.,16.ALPHA.,17,21-TETRAHYDROXYPREGNA-1,4-DIENE-3,20-DIONE CYCLIC 16,17-ACETAL WITH BUTYRALDEHYDE
Common Name English
Classification Tree Code System Code
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
WHO-ATC R03BA02
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
FDA ORPHAN DRUG 305710
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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
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
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
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
FDA ORPHAN DRUG 394613
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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
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
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
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
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
FDA ORPHAN DRUG 227406
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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
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
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
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
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
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
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
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
NCI_THESAURUS C521
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
WHO-ATC R01AD05
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
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
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
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
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
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
Code System Code Type Description
EVMPD
SUB05955MIG
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY
INN
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
PRIMARY
NCI_THESAURUS
C1027
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY
LACTMED
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
PRIMARY
PUBCHEM
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
PRIMARY
ECHA (EC/EINECS)
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
PRIMARY
DRUG BANK
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
PRIMARY
FDA UNII
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
PRIMARY
RXCUI
19831
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY RxNorm
MESH
D019819
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY
IUPHAR
7434
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY
DRUG CENTRAL
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
PRIMARY
CAS
51333-22-3
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY
USP_CATALOG
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
PRIMARY USP-RS
MERCK INDEX
M2746
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY Merck Index
EPA CompTox
51333-22-3
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY
WIKIPEDIA
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
PRIMARY
ChEMBL
CHEMBL1370
Created by admin on Fri Jun 25 21:05:48 UTC 2021 , Edited by admin on Fri Jun 25 21:05:48 UTC 2021
PRIMARY