Identification

Name
Desonide
Accession Number
DB01260
Type
Small Molecule
Groups
Approved, 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
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
DesonateGel0.5 mg/1gTopicalLEO Pharma Inc.2018-10-01Not applicableUs
DesonateGel0.5 mg/1gTopicalSkinMedica2007-03-30Not applicableUs
DesonateGel0.5 mg/1gTopicalBayer2006-10-20Not applicableUs
DesonateGel0.5 mg/1gTopicalIntendis Inc.2010-01-28Not applicableUs
DesonideCream0.5 mg/1gTopicalRebel Distributors2006-04-11Not applicableUs
DesonideOintment0.5 mg/1gTopicalPhysicians Total Care, Inc.2006-06-21Not applicableUs
DesonideCream0.5 mg/1gTopicalPerrigo New York Inc2006-04-11Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DesonideOintment0.5 mg/1gTopicalVersaPharm, Inc. - An Akorn Company2017-09-01Not applicableUs
DesonideCream0.5 mg/1gTopicalTiber Laboratories, LLC1992-06-302012-06-30Us
DesonideCream0.5 mg/1gTopicalProficient Rx LP2013-08-01Not applicableUs
DesonideOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.1994-08-03Not applicableUs
DesonideOintment0.5 mg/1gTopicalNorth Star Rx Llc2017-09-15Not applicableUs
DesonideLotion.5 mg/1gTopicalOwen Laboratories1984-12-14Not applicableUs
DesonideCream0.5 mg/1gTopicalNorth Star Rx Llc1992-06-30Not applicableUs
DesonideCream0.5 mg/1gTopicalGlenmark Pharmaceuticals Inc.,Usa2017-07-24Not applicableUs
DesonideLotion0.5 mg/1gTopicalPhysicians Total Care, Inc.2004-05-17Not applicableUs
DesonideLotion0.5 mg/1mLTopicalActavis Pharma Company2009-05-28Not applicableUs
International/Other Brands
Desocort (Galderma) / Tridesilon (Bayer)
Categories
UNII
J280872D1O
CAS number
638-94-8
Weight
Average: 416.5073
Monoisotopic: 416.219888756
Chemical Formula
C24H32O6
InChI Key
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
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.

Associated Conditions
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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0015389
KEGG Drug
D03696
PubChem Compound
5311066
PubChem Substance
46506186
ChemSpider
4470603
ChEBI
204734
ChEMBL
CHEMBL1201109
Therapeutic Targets Database
DAP001188
PharmGKB
PA164776996
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Desonide
ATC Codes
D07AB08 — DesonideD07BB02 — Desonide and antisepticsS01BA11 — Desonide
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingBasic ScienceHealthy Volunteers1
3CompletedTreatmentAtopic Dermatitis (AD)1
3CompletedTreatmentAtopic Dermatitis Eczema1
3Unknown StatusTreatmentAtopic Dermatitis (AD) / Dermatitis, Eczematous1
4CompletedTreatmentAtopic Dermatitis (AD)2
4CompletedTreatmentAtopic Dermatitis (AD) / Dermatitis, Eczematous1
4CompletedTreatmentHyperpigmentation1
4Not Yet RecruitingTreatmentPsoriasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Ameri-Pac Inc.
  • Contract Pharm
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DPT Laboratories Ltd.
  • E. Fougera and Co.
  • Galderma Laboratories
  • Intendis Inc.
  • Ivax Pharmaceuticals
  • Major Pharmaceuticals
  • Medisca Inc.
  • Nycomed Inc.
  • Palmetto Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmedix
  • Physicians Total Care Inc.
  • Stiefel Labs
  • Taro Pharmaceuticals USA
Dosage forms
FormRouteStrength
LotionTopical.05 %
GelTopical0.5 mg/1g
CreamTopical.5 mg/1g
LotionTopical.5 mg/1g
LotionTopical0.5 mg/1g
OintmentTopical0.5 mg/1g
CreamTopical0.5 mg/1g
LotionTopical0.5 mg/1mL
CreamTopical0.05 %
OintmentTopical0.05 %
CreamTopical.05 %
OintmentTopical.05 %
CreamTopical0.03 g/60g
CreamTopical.5 mg
OintmentTopical.5 mg
Aerosol, foamTopical0.05 %
Aerosol, foamTopical0.5 mg/1g
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)
US8460641No2013-06-112028-11-05Us
US8962000No2015-02-242025-08-31Us
US6730288No2004-05-042019-09-08Us
US7029659No2006-04-182019-09-08Us
US6387383No2002-05-142020-08-03Us
US9492384No2016-11-152025-08-31Us

Properties

State
Solid
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-3.8ALOGPS
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/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
show 5 more
Substituents
Progestogin-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
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
11beta-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 modula...
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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  2. Verdeso monograph [File]

Drug created on May 16, 2007 11:31 / Updated on November 16, 2018 11:19