BUDESONIDE

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 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 126 Target ID: CHEMBL340 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020441s020lbl.pdf	Substrate 656
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB01222	Binding Agent 1059		1.32 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 237 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020441s020lbl.pdf	Primary	Approved 8360	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
Distal ulcerative colitis 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205613s000lbl.pdf	Primary	Approved 8360	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
Perennial allergic rhinitis 47 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020746s026lbl.pdf	Palliative	Approved 8360	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
Crohn's disease 42 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021324s008lbl.pdf	Primary	Approved 8360	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

Title	Date	PubMed
Dysphonia caused by inhaled steroids: recognition of a characteristic laryngeal abnormality.	1983 Nov	6648863
Contact sensitivity and cross-reactivity of budesonide.	1993 Apr	8508630
[Contact allergy to topical glucocorticoids].	1993 Feb	8449700
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
Frequency of voice problems and cough in patients using pressurized aerosol inhaled steroid preparations.	1995 Apr	7664859
Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids.	1995 Jan	7826093
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
Deteriorating diabetic control associated with high-dose inhaled budesonide.	1999 Jul	10489860
Delayed generalized allergic reactions to corticosteroids.	2000	10894975
Transcriptional potencies of inhaled glucocorticoids.	2000 Jul	10903220
Comparison of hydrofluoroalkane-beclomethasone dipropionate Autohaler with budesonide Turbuhaler in asthma control.	2001	11694816
Prevention of mouse lung tumors by budesonide and its modulation of biomarkers.	2002 Jul	12117777
Inhibition of chemokine production from human airway smooth muscle cells by fluticasone, budesonide and beclomethasone.	2004	14643170
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.	2005 Aug	16101941
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
Resveratrol, an extract of red wine, inhibits lipopolysaccharide induced airway neutrophilia and inflammatory mediators through an NF-kappaB-independent mechanism.	2005 May	15734790
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
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
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
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
Budesonide/formoterol maintenance and reliever therapy in Asian patients (aged ≥16 years) with asthma: a sub-analysis of the COSMOS study.	2012 Jul 1	22607479
Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux.	2012 May 1	22464980
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).	2013 Dec	24014644
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

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