Desonide

Identification

Summary

Desonide is a topical corticosteroid used for the symptomatic treatment of inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.

Brand Names
Desonate, Desowen, Lokara, Tridesilon, Verdeso
Generic Name
Desonide
DrugBank Accession Number
DB01260
Background

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

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 416.5073
Monoisotopic: 416.219888756
Chemical Formula
C24H32O6
Synonyms
  • 11β,21-dihydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
  • 11β,21-dihydroxy-16α,17-isopropylidenedioxypregna-1,4-diene-3,20-dione
  • 11β,21-dihydroxy-16α,17α-isopropylidenedioxypregna-1,4-diene-3,20-dione
  • 16α-hydroxyprednisole-16,17-acetonide
  • 16α-hydroxyprednisolone-16α,17-acetonide
  • 16α,17α-isopropylidenedioxyprednisolone
  • Desfluorotriamcinolone acetonide
  • Desonida
  • Desonide
  • Desonidum
External IDs
  • D-2083
  • D2083

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Humans
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

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Desonide can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hyperglycemia can be increased when Desonide is combined with Acarbose.
AcetohexamideThe risk or severity of hyperglycemia can be increased when Desonide is combined with Acetohexamide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Desonide is combined with Acetyldigitoxin.
AlbiglutideThe risk or severity of hyperglycemia can be increased when Desonide is combined with Albiglutide.
AlogliptinThe risk or severity of hyperglycemia can be increased when Desonide is combined with Alogliptin.
AminoglutethimideThe therapeutic efficacy of Desonide can be decreased when used in combination with Aminoglutethimide.
Bacillus calmette-guerin substrain russian BCG-I live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Desonide.
BendroflumethiazideThe risk or severity of electrolyte imbalance can be increased when Desonide is combined with Bendroflumethiazide.
BenzthiazideThe risk or severity of electrolyte imbalance can be increased when Desonide is combined with Benzthiazide.
Interactions
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Food Interactions
No interactions found.

Products

Products
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International/Other Brands
Desocort (Galderma) / Tridesilon (Bayer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Desocort Cream 0.05%CreamTopicalGalderma1994-12-312007-08-02Canada flag
Desocort Lotion - 0.05%LotionTopicalGalderma1994-12-312016-08-04Canada flag
Desocort Ointment - 0.05%OintmentTopicalGalderma1994-12-312016-08-04Canada flag
DesonateGel0.5 mg/1gTopicalIntendis Inc.2010-01-28Not applicableUS flag
DesonateGel0.5 mg/1gTopicalLEO Pharma Inc.2018-10-01Not applicableUS flag
DesonateGel0.5 mg/1gTopicalSkinMedica2007-03-30Not applicableUS flag
DesonateGel0.5 mg/1gTopicalBayer HealthCare Pharmaceuticals Inc.2006-10-20Not applicableUS flag
DesonideOintment0.5 mg/1gTopicalPerrigo New York Inc2006-08-22Not applicableUS flag
DesonideCream0.5 mg/1gTopicalRebel Distributors2006-04-11Not applicableUS flag
DesonideOintment0.5 mg/1gTopicalPhysicians Total Care, Inc.2006-06-21Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DesonideCream0.5 mg/1gTopicalCadila Healthcare Limited2019-11-25Not applicableUS flag
DesonideOintment0.5 mg/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2001-03-12Not applicableUS flag
DesonideLotion0.5 mg/1mLTopicalAleor Dermaceuticals Limited2020-08-31Not applicableUS flag
DesonideLotion0.5 mg/1mLTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2002-03-19Not applicableUS flag
DesonideLotion.5 mg/1gTopicalOwen Laboratories, Inc.1984-12-142018-03-01US flag
DesonideOintment0.5 mg/1gTopicalAleor Dermaceuticals Limited2019-11-02Not applicableUS flag
DesonideCream0.5 mg/1gTopicalTiber Laboratories, LLC1992-06-302012-06-30US flag
DesonideOintment0.5 mg/1gTopicalAlembic Pharmaceuticals, Inc.2019-10-24Not applicableUS flag
DesonideCream0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.1992-06-30Not applicableUS flag
DesonideOintment0.5 mg/1gTopicalTeligent Pharma, Inc.2019-03-13Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DESONIDA CLIOQUINOL CREMA.Desonide (0.1 g) + Clioquinol (3 g)CreamTopical2006-11-10Not applicableColombia flag
PRECORT-A KREMDesonide (0.125 %) + Clioquinol (3 %)CreamTopicalKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
PRECORT-A POMADDesonide (0.125 %) + Clioquinol (3 %)OintmentTopicalKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
PREDNOL-A 30 GR KREMDesonide (0.125 %) + Clioquinol (3 %)CreamTopicalGENSENTA İLAÇ SANAYİ VE TİCARET A.Ş.2020-08-14Not applicableTurkey flag
PREDNOL-A 30 GR POMADDesonide (0.125 %) + Clioquinol (3 %)OintmentTopicalGENSENTA İLAÇ SANAYİ VE TİCARET A.Ş.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
S01BA11 — DesonideD07BB02 — Desonide and antisepticsD07AB08 — Desonide
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Alpha-hydroxy ketone
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)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
J280872D1O
CAS number
638-94-8
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[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
SMILES
[H][C@@]12C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

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
Human Metabolome Database
HMDB0015389
KEGG Drug
D03696
PubChem Compound
5311066
PubChem Substance
46506186
ChemSpider
4470603
RxNav
3254
ChEBI
204734
ChEMBL
CHEMBL1201109
ZINC
ZINC000004212851
Therapeutic Targets Database
DAP001188
PharmGKB
PA164776996
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Desonide
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAtopic Dermatitis (AD)2
4CompletedTreatmentAtopic Dermatitis (AD) / Dermatitis, Eczematous1
4CompletedTreatmentHyperpigmentation1
4Unknown StatusTreatmentPsoriasis1
3CompletedTreatmentAtopic Dermatitis (AD)1
3CompletedTreatmentAtopic Dermatitis Eczema1
3Unknown StatusTreatmentAtopic Dermatitis (AD) / Dermatitis, Eczematous1
1CompletedTreatmentVasoconstriction1
1RecruitingBasic ScienceHealthy Volunteers1

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
CreamTopical0.05 %
Ointment
SolutionTopical
Cream
GelTopical0.5 mg/1g
CreamTopical0.05 g
EmulsionTopical
LotionTopical
CreamTopical
EmulsionTopical0.05 g
CreamTopical.5 mg/1g
LotionTopical.5 mg/1g
LotionTopical0.5 mg/1g
OintmentTopical0.5 mg/1g
OintmentTopical0.5 mg/01g
SolutionTopical
CreamTopical0.5 mg/1g
CreamTopical
LotionTopical0.5 mg/1mL
OintmentTopical
OintmentTopical
OintmentOphthalmic
Solution / dropsOphthalmic
LotionTopical
CreamTopical0.1 g
CreamTopical0.03 g/60g
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)Region
US8460641No2013-06-112028-11-05US flag
US8962000No2015-02-242025-08-31US flag
US6730288No2004-05-042019-09-08US flag
US7029659No2006-04-182019-09-08US flag
US6387383No2002-05-142020-08-03US flag
US9492384No2016-11-152025-08-31US flag

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)13.75ChemAxon
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
Polarizability44.59 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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
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
Humans
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 17:31 / Updated on May 06, 2021 06:19