DEXBUDESONIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H34O6
Molecular Weight	430.5339
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 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(O[C@H](CCC)O2)C(=O)CO

InChI

InChIKey=VOVIALXJUBGFJZ-VXKMTNQYSA-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	430.5339
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23416292

Dexbudesonide (22R- Budesonide) is an epimer R of Budesonide, last is used as a mixture of 22R and 22S epimers for the topical treatment of asthma, rhinitis, and inflammatory bowel disease

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Budesonide for maintenance of remission in Crohn's disease.	2001	11279777
Ultrasonic nebulization system for respiratory drug delivery.	2001	11247278
Onset of bronchodilation of budesonide/formoterol vs. salmeterol/fluticasone in single inhalers.	2001	11162416
A comparison of topical budesonide and oral montelukast in seasonal allergic rhinitis and asthma.	2001 Apr	11359431
Quality of life indices may be predictive of placebo and medication response to treatment for allergic rhinitis.	2001 Apr	11345281
Airway epithelial cells release eosinophil survival-promoting factors (GM-CSF) after stimulation of proteinase-activated receptor 2.	2001 Apr	11295658
beta2-Adrenoceptor desensitization in human alveolar macrophages induced by inhaled terbutaline in vivo is not counteracted by budesonide.	2001 Apr	11256987
Intestinal luminal pH in inflammatory bowel disease: possible determinants and implications for therapy with aminosalicylates and other drugs.	2001 Apr	11247905
Nasal retention of budesonide and fluticasone in man: formation of airway mucosal budesonide-esters in vivo.	2001 Feb	11259988
Comparison of handling and acceptability of two spacer devices in young children with asthma.	2001 Feb	11236040
Switch from systemic steroids to budesonide in steroid dependent patients with inactive Crohn's disease.	2001 Feb	11156638
Novel glucocorticoid antedrugs possessing a 17beta-(gamma-lactone) ring.	2001 Feb 15	11170650
Tixocortol pivalate contact allergy in the GPMT: frequency and cross-reactivity.	2001 Jan	11156006
Pulmonary edema induced by allergen challenge in the rat: noninvasive assessment by magnetic resonance imaging.	2001 Jan	11146490
Pneumomediastinum and pneumopericardium: unusual and rare complications of asthma in a 4 years old girl.	2001 Jan-Feb	11449532
Effects of topical budesonide treatment on glucocorticoid receptor mRNA down-regulation and cytokine patterns in nasal polyps.	2001 Jan-Feb	11258648
Assessing the effect of intranasal steroids on growth.	2001 Jul	11449205
Effects of intranasal corticosteroids on the hypothalamic-pituitary-adrenal axis in children.	2001 Jul	11449204
Pharmacokinetics of intranasal corticosteroids.	2001 Jul	11449203
Proinflammatory cytokines and eosinophil cationic protein on glandular secretion from human nasal mucosa: regulation by corticosteroids.	2001 Jul	11447387
Infliximab for the treatment of Crohn's disease: review and indications for clinical use in Canada.	2001 Jun	11429666
Comparison of montelukast versus budesonide in the treatment of exercise-induced bronchoconstriction.	2001 Jun	11428738
Once-daily budesonide inhalation powder (Pulmicort Turbuhaler) maintains pulmonary function and symptoms of asthmatic children previously receiving inhaled corticosteroids.	2001 Jun	11428735
Once-daily budesonide via Turbuhaler improves symptoms in adults with persistent asthma.	2001 Jun	11428734
Interleukin-13 upregulates eotaxin expression in airway epithelial cells by a STAT6-dependent mechanism.	2001 Jun	11415942
The problem of dose-response and therapeutic ratio of inhaled steroids.	2001 Jun	11401902
On-demand relief treatment for asthma.	2001 Jun 9	11417576
[Solid combination of budesonide and formoterol in the treatment of bronchial asthma].	2001 Mar	11293852
The effectiveness of high-dose inhaled budesonide therapy in the treatment of acute asthma exacerbations in children.	2001 Mar	11289332
Use of inhaled corticosteroids and risk of fractures.	2001 Mar	11277277
FeNO measured at fixed exhalation flow rate during controlled tidal breathing in children from the age of 2 yr.	2001 Mar	11254527
Comparison of the systemic effects of fluticasone propionate and budesonide given by dry powder inhaler in healthy and asthmatic subjects.	2001 Mar	11182010
Effect of budesonide and nedocromil sodium on IL-6 and IL-8 release from human nasal mucosa and polyp epithelial cells.	2001 May	11392584
Approach to corticosteroid-dependent and corticosteroid-refractory Crohn's disease.	2001 May	11380040
The linear relationship between changes in childhood growth velocity and topical glucocorticoid dose.	2001 May-Jun	11424876

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

In vitro biotransformation of the 22R (Dexbudesonide) and 22S epimers of the topical steroid budesonide was studied in the S-9 fraction of human liver, bronchus, skin and colonic mucosa. A marked decay of the initial concentration of unchanged budesonide epimers was noticed after 2 h incubation in cultured human hepatocytes, while only a small decrease was observed after 24 h incubation in cultured human airway smooth muscle cells and BEAS-2B cells. The 22R epimer of budesonide suffered greater in vitro biotransformation than the 22S epimer in human hepatic, bronchial and colonic tissues.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:55:59 GMT 2023` Edited by `admin` on `Fri Dec 15 15:55:59 GMT 2023`
Record UNII	2HI1006KPH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXBUDESONIDE

Official Name

English

dexbudesonide [INN]

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 16,17-BUTYLIDENEBIS(OXY)-11,21-DIHYDROXY-, (11.BETA.16.ALPHA.(R))

Common Name

English

Dexbudesonide [WHO-DD]

Common Name

English

(R)-11.BETA.,16.ALPHA.,17,21-TETRAHYDROXYPREGNA-1,4-DIENE-3,20-DIONE 16,17-ACETAL WITH BUTYRALDEHYDE

Common Name

English

R-BUDESONIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C521