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

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

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

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 116 Target ID: CHEMBL340 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020441s020lbl.pdf	Substrate 609
Glucocorticoid receptor 167 Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB01222	Binding Agent 996		1.32 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 227 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020441s020lbl.pdf	Primary	Approved 8043	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 8043	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 45 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020746s026lbl.pdf	Palliative	Approved 8043	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 37 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021324s008lbl.pdf	Primary	Approved 8043	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
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
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 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	10850854
Effects of topical glucocorticoids on in vitro lactoferrin glandular secretion: comparison between human upper and lower airways.	2000 Dec	11112886
Transcriptional potencies of inhaled glucocorticoids.	2000 Jul	10903220
Inhibition of GM-CSF secretion by topical corticosteroids and nedocromil sodium. A comparison study using nasal polyp epithelial cells.	2000 May	10868704
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	11158452
Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis.	2001 Nov 23	11730731
Budesonide-induced acute hepatitis in an HIV-positive patient with ritonavir as a co-medication.	2002 May 24	12004282
The locally acting glucocorticosteroid budesonide enhances intestinal sugar uptake following intestinal resection in rats.	2003 Feb	12524409
Stimulating effect of glucocorticosteroids on intestinal fructose transport in rats is increased by feeding a saturated fatty acid diet.	2003 Nov	14705828
Neuropsychologic changes and inhaled corticosteroids.	2004 Aug	15341026
Comparison of in vitro-activity of commonly used topical glucocorticoids on cytokine- and phospholipase inhibition.	2004 Aug 31	15337628
Effects of different anti-asthmatic agents on induced sputum and eosinophil cationic protein in mild asthmatics.	2004 Nov	15612964
Generalized seizure in a Mauritian woman taking bupropion.	2004 Oct	15526043
A randomized phase IIb trial of pulmicort turbuhaler (budesonide) in people with dysplasia of the bronchial epithelium.	2004 Oct 1	15475437
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	15362971
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
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
Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids.	2006 Mar	16507850
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
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
Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake.	2011 Jun	21430235
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
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
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	25313925
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
Thiobenzothiazole-modified Hydrocortisones Display Anti-inflammatory Activity with Reduced Impact on Islet β-Cell Function.	2015 May 22	25851902

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).

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:05:48 UTC 2021` Edited by `admin` on `Fri Jun 25 21:05:48 UTC 2021`
Record UNII	Q3OKS62Q6X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BUDESONIDE

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