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

Details

Stereochemistry EPIMERIC
Molecular Formula C25H34O6
Molecular Weight 430.5339
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUDESONIDE

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

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

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

2000
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

2013
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

2015
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

2001
PubMed

PubMed

TitleDatePubMed
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
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
AIRSUPRA COMPONENT BUDESONIDE
Brand Name English
Budesonide [WHO-DD]
Common 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 [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
BUDESONIDE COMPONENT OF AIRSUPRA
Brand 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)-11β,16α,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 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
EVMPD
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
INN
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
DAILYMED
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
NCI_THESAURUS
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
LACTMED
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
PUBCHEM
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
ECHA (EC/EINECS)
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
DRUG BANK
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
FDA UNII
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
RXCUI
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
MESH
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
CHEBI
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
IUPHAR
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
RS_ITEM_NUM
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
DRUG CENTRAL
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
CAS
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
MERCK INDEX
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
NSC
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
EPA CompTox
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
WIKIPEDIA
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
ChEMBL
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