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Identification
NameDesonide
Accession NumberDB01260
Typesmall molecule
Groupsapproved, investigational
Description

A nonfluorinated corticosteroid anti-inflammatory agent used topically for dermatoses. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
DesocortGalderma
DesonateNot Available
DesowenGalderma
LoKaraNot Available
TridesilonBayer
VerdesoNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number638-94-8
WeightAverage: 416.5073
Monoisotopic: 416.219888756
Chemical FormulaC24H32O6
InChI KeyWBGKWQHBNHJJPZ-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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsKetosteroids; Hydroxysteroids; Cyclohexanols; 1,3-Dioxolanes; Cyclic Alcohols and Derivatives; Ketones; Enolates; Polyamines; Acetals; Primary Alcohols; Aldehydes
Substituents20-keto-steroid; 11-hydroxy-steroid; 3-keto-steroid; cyclohexanol; meta-dioxolane; cyclic alcohol; ketone; secondary alcohol; primary alcohol; enolate; ether; polyamine; acetal; carbonyl group; aldehyde; alcohol
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationFor the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatose.
PharmacodynamicsDesonide 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 actionLike 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.
AbsorptionTopical corticosteroids can be absorbed from normal intact skin, inflammation and/or other disease processes in the skin may increase percutaneous absorption.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9764
Blood Brain Barrier + 0.9382
Caco-2 permeable - 0.6162
P-glycoprotein substrate Substrate 0.7998
P-glycoprotein inhibitor I Non-inhibitor 0.5837
P-glycoprotein inhibitor II Inhibitor 0.6045
Renal organic cation transporter Non-inhibitor 0.7573
CYP450 2C9 substrate Non-substrate 0.8268
CYP450 2D6 substrate Non-substrate 0.9078
CYP450 3A4 substrate Substrate 0.7545
CYP450 1A2 substrate Non-inhibitor 0.909
CYP450 2C9 substrate Non-inhibitor 0.8729
CYP450 2D6 substrate Non-inhibitor 0.9544
CYP450 2C19 substrate Non-inhibitor 0.9521
CYP450 3A4 substrate Non-inhibitor 0.536
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9129
Ames test Non AMES toxic 0.8938
Carcinogenicity Non-carcinogens 0.949
Biodegradation Not ready biodegradable 0.9766
Rat acute toxicity 2.5316 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9573
hERG inhibition (predictor II) Non-inhibitor 0.67
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
FormRouteStrength
CreamTopical
LotionTopical
OintmentTopical
Prices
Unit descriptionCostUnit
DesOwen Lot w/Cetaphil Cream 0.05% Kit Box255.84USDbox
Desowen 0.05% ointment kit217.2USDkit
Desowen 0.05% cream kit212.4USDkit
DesOwen 0.05% Lotion 118ml Bottle183.17USDbottle
Desonide powder152.39USDg
DesOwen 0.05% Lotion 59ml Bottle123.38USDbottle
Desonide 0.05% Lotion 118ml Bottle76.75USDbottle
Desonide 0.05% Lotion 59ml Bottle50.86USDbottle
Desonide 0.05% Ointment 60 gm Tube41.76USDtube
Desonide 0.05% Cream 60 gm Tube41.48USDtube
Desonide 0.05% Ointment 15 gm Tube16.09USDtube
Desonide 0.05% Cream 15 gm Tube16.07USDtube
Desowen 0.05% cream2.43USDg
Desonide 0.05% cream0.81USDg
Desocort 0.05 % Ointment0.32USDg
Pms-Desonide 0.05 % Cream0.28USDg
Pms-Desonide 0.05 % Ointment0.28USDg
Desocort 0.05 % Lotion0.16USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States63873832000-08-032020-08-03
United States67302881999-09-082019-09-08
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point257-260Bernstein, S. and Allen, G.R., Jr.; U.S. Patent 2,990,401; June 27, 1961; assigned to American Cyanamid Company. Diassi, P.A. and Principe, P.A.; U.S.Patent 3,549,498; December 22, 1970; assigned to E.R. Squibb & Sons, inc.
water solubilityPractically insolubleNot Available
logP1.4Not Available
Predicted Properties
PropertyValueSource
water solubility5.94e-02 g/lALOGPS
logP2.31ALOGPS
logP1.9ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)13.74ChemAxon
pKa (strongest basic)-2.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count2ChemAxon
polar surface area93.06ChemAxon
rotatable bond count2ChemAxon
refractivity112.06ChemAxon
polarizability44.77ChemAxon
number of rings5ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Bernstein, S. and Allen, G.R., Jr.; U.S. Patent 2,990,401; June 27, 1961; assigned to
American Cyanamid Company.
Diassi, P.A. and Principe, P.A.; U.S.Patent 3,549,498; December 22, 1970; assigned to
E.R. Squibb & Sons, inc.

General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD03696
PubChem Compound5311066
PubChem Substance46506186
ChemSpider4470603
ChEBI204734
ChEMBLCHEMBL1201109
Therapeutic Targets DatabaseDAP001188
PharmGKBPA164776996
Drug Product Database2048639
RxListhttp://www.rxlist.com/cgi/generic/desonide.htm
Drugs.comhttp://www.drugs.com/cdi/desonide-cream.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/tri1457.shtml
WikipediaDesonide
ATC CodesS01BA11D07AB08
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

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

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Drug created on May 16, 2007 11:31 / Updated on April 10, 2014 13:55