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Identification
Name Desonide
Accession Number DB01260
Type small molecule
Groups approved
Description

A nonfluorinated corticosteroid anti-inflammatory agent used topically for dermatoses. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Desilux
Desocort
Desowen
Tridesilon
Brand mixtures Not Available
Categories
  • Anti-inflammatory Agents
CAS number 638-94-8
Weight Average: 416.5073
Monoisotopic: 416.219888756
Chemical Formula C24H32O6
InChI Key InChIKey=WBGKWQHBNHJJPZ-LECWWXJVSA-N
InChI
InChI=1S/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1
Plain Text
IUPAC Name
(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
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(C)(C)O2)C(=O)CO
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetals and Derivatives
  • Ethers
  • Dioxoles
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Ketones
Pharmacology
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatose.
Pharmacodynamics Desonide is a synthetic nonfluorinated corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents.
Mechanism of action Like other topical corticosteroids, desonide has anti-inflammatory, antipruritic and vasoconstrictive properties. The drug binds to cytosolic glucocorticoid receptors. This complex migrates to the nucleus and binds to genetic elements on the DNA. This activates and represses various genes. However corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
Absorption Topical corticosteroids can be absorbed from normal intact skin, inflammation and/or other disease processes in the skin may increase percutaneous absorption.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Stiefel laboratories inc
  • Perrigo new york inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Galderma laboratories lp
  • Intendis inc
  • Altana inc
Packagers
Dosage forms
Form Route Strength
Cream Topical
Lotion Topical
Ointment Topical
Prices
Unit description Cost Unit
DesOwen Lot w/Cetaphil Cream 0.05% Kit Box 255.84 USD box
Desowen 0.05% ointment kit 217.2 USD kit
Desowen 0.05% cream kit 212.4 USD kit
DesOwen 0.05% Lotion 118ml Bottle 183.17 USD bottle
Desonide powder 152.39 USD g
DesOwen 0.05% Lotion 59ml Bottle 123.38 USD bottle
Desonide 0.05% Lotion 118ml Bottle 76.75 USD bottle
Desonide 0.05% Lotion 59ml Bottle 50.86 USD bottle
Desonide 0.05% Ointment 60 gm Tube 41.76 USD tube
Desonide 0.05% Cream 60 gm Tube 41.48 USD tube
Desonide 0.05% Ointment 15 gm Tube 16.09 USD tube
Desonide 0.05% Cream 15 gm Tube 16.07 USD tube
Desowen 0.05% cream 2.43 USD g
Desonide 0.05% cream 0.81 USD g
Desocort 0.05 % Ointment 0.32 USD g
Pms-Desonide 0.05 % Cream 0.28 USD g
Pms-Desonide 0.05 % Ointment 0.28 USD g
Desocort 0.05 % Lotion 0.16 USD g
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Patents
Country Patent Number Approved Expires (estimated)
United States 6387383 2000-08-03 2020-08-03
United States 6730288 1999-09-08 2019-09-08
Properties
State solid
Experimental Properties
Property Value Source
melting point 274 °C PhysProp
water solubility Practically insoluble Not Available
logP 1.4 Not Available
Predicted Properties
Property Value Source
water solubility 5.94e-02 g/l ALOGPS
logP 2.31 ALOGPS
logP 1.9 ChemAxon
logS -3.9 ALOGPS
pKa (strongest acidic) 13.74 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 93.06 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 112.06 ChemAxon
polarizability 44.77 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D03696 Link_out
PubChem Compound 5311066 Link_out
PubChem Substance 46506186 Link_out
ChemSpider 4470603 Link_out
ChEBI 204734 Link_out
ChEMBL 204734 Link_out
Therapeutic Targets Database DAP001188 Link_out
PharmGKB PA164776996 Link_out
Drug Product Database 2048639 Link_out
RxList http://www.rxlist.com/cgi/generic/desonide.htm Link_out
Drugs.com http://www.drugs.com/cdi/desonide-cream.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/tri1457.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Desonide Link_out
ATC Codes
  • D07AC09
  • R03BA02
  • S01BA11
  • A07EA06
  • D07AB08
  • R01AD05
AHFS Codes
  • 84:06.00
PDB Entries Not Available
FDA label Not Available
MSDS show (73.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Russell GM, Henley DE, Leendertz J, Douthwaite JA, Wood SA, Stevens A, Woltersdorf WW, Peeters BW, Ruigt GS, White A, Veldhuis JD, Lightman SL: Rapid glucocorticoid receptor-mediated inhibition of hypothalamic-pituitary-adrenal ultradian activity in healthy males. J Neurosci. 2010 Apr 28;30(17):6106-15. Pubmed
  2. Shaw JR, Gabor K, Hand E, Lankowski A, Durant L, Thibodeau R, Stanton CR, Barnaby R, Coutermarsh B, Karlson KH, Sato JD, Hamilton JW, Stanton BA: Role of glucocorticoid receptor in acclimation of killifish (Fundulus heteroclitus) to seawater and effects of arsenic. Am J Physiol Regul Integr Comp Physiol. 2007 Feb;292(2):R1052-60. Epub 2006 Oct 12. Pubmed
  3. Otte C, Wust S, Zhao S, Pawlikowska L, Kwok PY, Whooley MA: Glucocorticoid receptor gene, low-grade inflammation, and heart failure: the Heart and Soul study. J Clin Endocrinol Metab. 2010 Jun;95(6):2885-91. Epub 2010 Apr 6. Pubmed
Comments
Drug created on May 16, 2007 11:31 / Updated on February 08, 2013 16:20