Identification
NameDesonide
Accession NumberDB01260
TypeSmall Molecule
GroupsApproved, Investigational
Description

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

Structure
Thumb
Synonyms
11beta,21-Dihydroxy-16alpha,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
11beta,21-Dihydroxy-16alpha,17-isopropylidenedioxypregna-1,4-diene-3,20-dione
11beta,21-Dihydroxy-16alpha,17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione
16alpha-Hydroxyprednisole-16,17-acetonide
16alpha-Hydroxyprednisolone-16alpha,17-acetonide
16alpha,17alpha-Isopropylidenedioxyprednisolone
Desfluorotriamcinolone acetonide
Desonida
Desonidum
External IDs D-2083 / D2083
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desocort Cream 0.05%Cream.05 %TopicalGalderma1994-12-312007-08-02Canada
Desocort Lotion - 0.05%Lotion.05 %TopicalGalderma1994-12-312016-08-04Canada
Desocort Ointment - 0.05%Ointment.05 %TopicalGalderma1994-12-312016-08-04Canada
DesonateGel.5 mg/gTopicalIntendis Inc.2010-01-28Not applicableUs
DesonateGel.5 mg/gTopicalBayer2006-10-20Not applicableUs
DesonideCream.5 mg/gTopicalRebel Distributors2006-04-11Not applicableUs
DesonideOintment.5 mg/gTopicalPhysicians Total Care, Inc.2006-06-21Not applicableUs
DesonideCream.5 mg/gTopicalProficient Rx LP2013-08-01Not applicableUs
DesonideCream.5 mg/gTopicalPerrigo New York Inc.2006-04-11Not applicableUs
DesonideCream.5 mg/gTopicalActavis Pharma Company2013-08-01Not applicableUs
DesonideCream.5 mg/gTopicalOwen Laboratories1984-12-14Not applicableUs
DesonideOintment.5 mg/gTopicalPerrigo New York Inc.2006-08-22Not applicableUs
DesonideCream.5 mg/gTopicalPhysicians Total Care, Inc.2006-04-11Not applicableUs
DesowenCream.5 mg/gTopicalGalderma1984-12-14Not applicableUs
Pdp-desonideOintment0.05 %TopicalPendopharm Division Of De Pharmascience Inc1997-01-14Not applicableCanada
Pdp-desonideCream0.05 %TopicalPendopharm Division Of De Pharmascience Inc1997-01-14Not applicableCanada
Tridesilon 0.05% Desonide CreamCream.05 %TopicalPerrigo International1996-11-11Not applicableCanada
Tridesilon 0.05% Desonide OintmentOintment.05 %TopicalPerrigo International1998-01-27Not applicableCanada
Tridesilon CreamCream.03 g/60gTopicalEncore Dermatology Inc2016-10-01Not applicableUs
Tridesilon Crm 0.05%Cream.5 mgTopicalMiles Inc. Pharmaceutical Division1978-12-311998-09-25Canada
Tridesilon Ont 0.05%Ointment.5 mgTopicalMiles Inc. Pharmaceutical Division1978-12-311998-09-25Canada
VerdesoAerosol, foam0.05 %TopicalGlaxosmithkline Inc2011-04-202016-04-13Canada
VerdesoAerosol, foam.5 mg/gTopicalAqua Pharmaceuticals2006-10-06Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DesonideCream.5 mg/gTopicalNorth Star Rx Llc1992-06-30Not applicableUs
DesonideOintment.5 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.1994-08-03Not applicableUs
DesonideLotion.5 mg/mLTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2002-03-19Not applicableUs
DesonideLotion.5 mg/mLTopicalTaro Pharmaceuticals U.S.A., Inc.2014-10-31Not applicableUs
DesonideLotion.5 mg/mLTopicalActavis Pharma Company2009-05-28Not applicableUs
DesonideCream.5 mg/gTopicalGw Pharmaceuticals Ltd.2015-06-29Not applicableUs
DesonideLotion.5 mg/gTopicalPhysicians Total Care, Inc.2004-05-17Not applicableUs
DesonideCream.5 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.1992-06-30Not applicableUs
DesonideOintment.5 mg/gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2001-03-12Not applicableUs
DesonideCream.5 mg/gTopicalRebel Distributors1992-06-30Not applicableUs
DesonideLotion.5 mg/gTopicalOwen Laboratories1984-12-14Not applicableUs
DesowenLotion.5 mg/gTopicalGalderma1988-07-15Not applicableUs
LokaraLotion.5 mg/mLTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2002-03-19Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DesocortGalderma
TridesilonBayer
Brand mixturesNot Available
Categories
UNIIJ280872D1O
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[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]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
Pharmacology
Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatose.

Structured Indications
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Glucocorticoid receptorProteinyes
agonist
HumanP04150 details
Related Articles
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 distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesD07BB02 — Desonide and antisepticsD07AB08 — DesonideS01BA11 — Desonide
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.7 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentModerate, refractory Atopic dermatitis1
3Unknown StatusTreatmentDermatitis, Eczematous / Moderate, refractory Atopic dermatitis1
4CompletedTreatmentDermatitis, Eczematous / Moderate, refractory Atopic dermatitis1
4CompletedTreatmentHyperpigmentation1
4CompletedTreatmentModerate, refractory Atopic dermatitis1
4Not Yet RecruitingTreatmentPsoriasis1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
LotionTopical.05 %
GelTopical.5 mg/g
OintmentTopical.5 mg/g
CreamTopical.5 mg/g
LotionTopical.5 mg/g
LotionTopical.5 mg/mL
CreamTopical0.05 %
OintmentTopical0.05 %
CreamTopical.05 %
OintmentTopical.05 %
CreamTopical.03 g/60g
CreamTopical.5 mg
OintmentTopical.5 mg
Aerosol, foamTopical.5 mg/g
Aerosol, foamTopical0.05 %
Prices
Unit descriptionCostUnit
DesOwen Lot w/Cetaphil Cream 0.05% Kit Box255.84USD box
Desowen 0.05% ointment kit217.2USD kit
Desowen 0.05% cream kit212.4USD kit
DesOwen 0.05% Lotion 118ml Bottle183.17USD bottle
Desonide powder152.39USD g
DesOwen 0.05% Lotion 59ml Bottle123.38USD bottle
Desonide 0.05% Lotion 118ml Bottle76.75USD bottle
Desonide 0.05% Lotion 59ml Bottle50.86USD bottle
Desonide 0.05% Ointment 60 gm Tube41.76USD tube
Desonide 0.05% Cream 60 gm Tube41.48USD tube
Desonide 0.05% Ointment 15 gm Tube16.09USD tube
Desonide 0.05% Cream 15 gm Tube16.07USD tube
Desowen 0.05% cream2.43USD g
Desonide 0.05% cream0.81USD g
Desocort 0.05 % Ointment0.32USD g
Pms-Desonide 0.05 % Cream0.28USD g
Pms-Desonide 0.05 % Ointment0.28USD g
Desocort 0.05 % Lotion0.16USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6387383 No2000-08-032020-08-03Us
US6730288 No1999-09-082019-09-08Us
US7029659 No1999-09-082019-09-08Us
US8460641 No2008-11-052028-11-05Us
US8962000 No2005-08-312025-08-31Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)257-260Bernstein, 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 Solubility0.0594 mg/mLALOGPS
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 Area93.06 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity112.06 m3·mol-1ChemAxon
Polarizability44.77 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9764
Blood Brain Barrier+0.9382
Caco-2 permeable-0.6162
P-glycoprotein substrateSubstrate0.7998
P-glycoprotein inhibitor INon-inhibitor0.5837
P-glycoprotein inhibitor IIInhibitor0.6045
Renal organic cation transporterNon-inhibitor0.7573
CYP450 2C9 substrateNon-substrate0.8268
CYP450 2D6 substrateNon-substrate0.9078
CYP450 3A4 substrateSubstrate0.7545
CYP450 1A2 substrateNon-inhibitor0.909
CYP450 2C9 inhibitorNon-inhibitor0.8729
CYP450 2D6 inhibitorNon-inhibitor0.9544
CYP450 2C19 inhibitorNon-inhibitor0.9521
CYP450 3A4 inhibitorNon-inhibitor0.536
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9129
Ames testNon AMES toxic0.8938
CarcinogenicityNon-carcinogens0.949
BiodegradationNot ready biodegradable0.9766
Rat acute toxicity2.5316 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9573
hERG inhibition (predictor II)Non-inhibitor0.67
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative ParentsGluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo delta-1,4-steroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Ketals / Alpha-hydroxy ketones / 1,3-dioxolanes / Secondary alcohols / Cyclic ketones
SubstituentsProgestogin-skeleton / 21-hydroxysteroid / 20-oxosteroid / Pregnane-skeleton / 3-oxosteroid / 3-oxo-delta-1,4-steroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / Oxosteroid / Delta-1,4-steroid
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors11beta-hydroxy steroid, cyclic ketal, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, corticosteroid, 21-hydroxy steroid (CHEBI:204734 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, 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 grow...
Gene Name:
NR3C1
Uniprot ID:
P04150
Uniprot Name:
Glucocorticoid receptor
Molecular Weight:
85658.57 Da
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. doi: 10.1523/JNEUROSCI.5332-09.2010. [PubMed:20427668 ]
  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:17038445 ]
  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. doi: 10.1210/jc.2009-2251. Epub 2010 Apr 6. [PubMed:20371666 ]
Drug created on May 16, 2007 11:31 / Updated on July 27, 2017 16:02