Budesonide

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020441s020lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020441s020lbl.pdf	Substrate 661
Glucocorticoid receptor 173 Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB01222	Binding Agent 1076		1.32 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020441s020lbl.pdf	Primary	Approved 8583	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
Distal ulcerative colitis 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205613s000lbl.pdf	Primary	Approved 8583	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
Perennial allergic rhinitis 47 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020746s026lbl.pdf	Palliative	Approved 8583	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
Crohn's disease 64 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021324s008lbl.pdf	Primary	Approved 8583	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

Title	Date	PubMed
Methodological aspects on clinical trials with inhaled corticosteroids: results of two comparisons between two steroid aerosols in patients with asthma.	1982	6958474
Contact sensitivity and cross-reactivity of budesonide.	1993 Apr	8508630
Contact allergies to topical corticosteroids.	1993 Mar	8462297
The effect of different corticosteroids and cyclosporin A on interleukin-4 and interleukin-5 release from murine TH2-type T cells.	1994 Aug 1	7988651
Effect of terfenadine and budesonide on nasal symptoms, olfaction, and nasal airway patency following allergen challenge.	1995 Aug	7503405
Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids.	1995 Jan	7826093
Effects of glucocorticoids on lymphocyte activation in patients with steroid-sensitive and steroid-resistant asthma.	1996 Dec	8977508
Induction of the E-selectin promoter by interleukin 1 and tumour necrosis factor alpha, and inhibition by glucocorticoids.	1997 Dec 1	9371735
The effects of inhaled glucocorticoids on bone mass and biochemical markers of bone homeostasis: a 1-year study of beclomethasone versus budesonide.	1997 Jun	9232087
[Steroid-induced myopathy in left-sided ulcerative colitis. Successful treatment and continued therapy with the topical steroid budesonide].	1997 Jun 15	9297069
Severe hypokalemia after budesonide treatment for Crohn's disease.	1997 Mar	9138184
Effects of different anti-asthmatic agents on induced sputum and eosinophil cationic protein in mild asthmatics.	2004 Nov	15612964
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.	2005 Aug	16101941
Novel sulfhydryl-reactive compounds orazipone and OR-1958 inhibit cytokine production and histamine release in rat and human mast cells.	2005 Jan	15589479
Intratracheal budesonide-poly(lactide-co-glycolide) microparticles reduce oxidative stress, VEGF expression, and vascular leakage in a benzo(a)pyrene-fed mouse model.	2005 Jul	15969944
The effect of intranasal steroid budesonide on the congestion-related sleep disturbance and daytime somnolence in patients with perennial allergic rhinitis.	2005 Jul-Aug	16270719
Chemoprevention: mouse colon and lung tumor bioassay and modulation of DNA methylation as a biomarker.	2005 Mar	15824018
Effect of inhaled corticosteroid on an immunoreactive thymus and activation-regulated chemokine expression in the bronchial biopsies from asthmatics.	2005 Mar	15679716
Resveratrol, an extract of red wine, inhibits lipopolysaccharide induced airway neutrophilia and inflammatory mediators through an NF-kappaB-independent mechanism.	2005 May	15734790
The combined effects of zafirlukast, prednisone, and inhaled budesonide on IL-13 and IFN-gamma secretion.	2005 Sep	16160912
Reversible dementia with parkinsonian features associated with budesonide use.	2006 Aug 22	16924038
Prevention of mouse lung tumors and modulation of DNA methylation by combined treatment with budesonide and R115777 (ZarnestraMT).	2006 Dec	16733249
Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids.	2006 Mar	16507850
[Effects of beclomethasone dipropionate and budesonide on interleukin-13 induced cytokine release, proliferation and differentiation of the human lung fibroblasts].	2007 Aug	17988555
Modulation by budesonide of DNA methylation and mRNA expression in mouse lung tumors.	2007 Mar 1	17163412
The effect of corticosteroids on the disposal of long-acting beta2-agonists by airway smooth muscle cells.	2007 Nov	17920670
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Oxidative stress modulates theophylline effects on steroid responsiveness.	2008 Dec 19	18951874
Tolerance and rebound with zafirlukast in patients with persistent asthma.	2008 May 19	18489783
A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions.	2008 Oct	18812576
Mass casualties from acute inhalation of chlorine gas.	2009 Dec	20016425
Thirteen-year follow-up of early intervention with an inhaled corticosteroid in patients with asthma.	2009 Dec	20004779
Management of Crohn's disease in adults.	2009 Feb	19174807
Contact allergy to topical corticosteroids--results from the IVDK and epidemiological risk assessment.	2009 Jan	18761609
Expression and regulation of the bile acid transporter, OSTalpha-OSTbeta in rat and human intestine and liver.	2009 Jul	19562681
Budesonide prevents cytokine-induced decrease of the relaxant responses to formoterol and terbutaline, but not to salmeterol, in mouse trachea.	2010 Apr	20061444
Recurrent spontaneous gastrointestinal graft-versus-host disease in autologous hematopoietic stem cell transplantation.	2010 Feb	20223723
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.	2010 Jul	20116850
Rapid nongenomic actions of inhaled corticosteroids on long-acting β(2)-agonist transport in the airway.	2011 Dec	21914487
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	20888898
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake.	2011 Jun	21430235
Activities of aldo-keto reductase 1 enzymes on two inhaled corticosteroids: implications for the pharmacological effects of inhaled corticosteroids.	2011 May 30	21276783
Hyalinization of the pyloric stomach in CD-1 mice following oral (dietary) administration of the corticosteroid agonists mometasone furoate, budesonide, and flunisolide.	2011 Oct	21885873
Contact sensitization in very young children.	2011 Oct	21616561
Design and synthesis of long acting inhaled corticosteroids for the treatment of asthma.	2011 Oct 1	21880489
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	21782008
Review article: a decision-making algorithm for the management of pregnancy in the inflammatory bowel disease patient.	2012 Mar	22221203
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453
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	25752796

Patents

Sample Use Guides

In Vivo Use Guide

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

Official Name

English

ENTOCORT EC

Preferred 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

EOHILIA

Brand Name

English

UCERIS COMPONENT BUDESONIDE

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

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

(RS)-11?,16?,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