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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
Synonyms
SynonymLanguageCode
11beta,21-Dihydroxy-16alpha,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dioneNot AvailableNot Available
11beta,21-Dihydroxy-16alpha,17-isopropylidenedioxypregna-1,4-diene-3,20-dioneNot AvailableNot Available
11beta,21-Dihydroxy-16alpha,17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dioneNot AvailableNot Available
16alpha-Hydroxyprednisole-16,17-acetonideNot AvailableNot Available
16alpha-Hydroxyprednisolone-16alpha,17-acetonideNot AvailableNot Available
16alpha,17alpha-IsopropylidenedioxyprednisoloneNot AvailableNot Available
Desfluorotriamcinolone acetonideNot AvailableNot Available
DesonidaNot AvailableNot Available
DesonidumNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desowencream.5 mg/gtopicalGalderma Laboratories, L.P.1984-12-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidecream.5 mg/gtopicalActavis Mid Atlantic LLC2013-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonategel.5 mg/gtopicalIntendis Inc.2010-01-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Verdesoaerosol, foam.5 mg/gtopicalAqua Pharmaceuticals2006-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidecream.5 mg/gtopicalRebel Distributors Corp2006-04-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidecream.5 mg/gtopicalPerrigo New York Inc2006-04-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonideointment.5 mg/gtopicalPerrigo New York Inc2006-08-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonategel.5 mg/gtopicalBayer Health Care Pharmaceuticals Inc.2006-10-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidecream.5 mg/gtopicalPhysicians Total Care, Inc.2006-04-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonideointment.5 mg/gtopicalPhysicians Total Care, Inc.2006-06-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidelotion.5 mg/gtopicalOwen Laboratories, Inc.1984-12-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidecream.5 mg/gtopicalOwen Laboratories, Inc.1984-12-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Verdesoaerosol, foam0.05 %topicalGlaxosmithkline IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desonideointment.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2010-10-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidelotion.5 mg/1000mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2002-03-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desowenlotion.5 mg/gtopicalGalderma Laboratories, L.P.1988-07-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Lokaralotion.5 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2002-03-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidelotion.5 mg/mLtopicalActavis Mid Atlantic LLC, Lincolnton, NC 280922009-05-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidecream.5 mg/gtopicalRebel Distributors Corp1992-06-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidecream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1992-06-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonideointment.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1994-08-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidelotion.5 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.2014-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desonidelotion.5 mg/gtopicalPhysicians Total Care, Inc.2004-05-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
DesocortGalderma
TridesilonBayer
Brand mixturesNot Available
SaltsNot 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[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]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
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 Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Meta-dioxolane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
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 substrateNon-inhibitor0.8729
CYP450 2D6 substrateNon-inhibitor0.9544
CYP450 2C19 substrateNon-inhibitor0.9521
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Aerosol, foamtopical.5 mg/g
Aerosol, foamtopical0.05 %
Creamtopical.5 mg/g
Geltopical.5 mg/g
Lotiontopical.5 mg/1000mL
Lotiontopical.5 mg/g
Lotiontopical.5 mg/mL
Ointmenttopical.5 mg/g
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
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 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesD07AB08S01BA11
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (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