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

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Desocort Cream 0.05%	Cream	.05 %	Topical	Galderma	1994-12-31	2007-08-02
Desocort Lotion - 0.05%	Lotion	.05 %	Topical	Galderma	1994-12-31	2016-08-04
Desocort Ointment - 0.05%	Ointment	.05 %	Topical	Galderma	1994-12-31	2016-08-04
Desonate	Gel	0.5 mg/1g	Topical	SkinMedica	2007-03-30	Not applicable
Desonate	Gel	0.5 mg/1g	Topical	Bayer	2006-10-20	Not applicable
Desonate	Gel	0.5 mg/1g	Topical	LEO Pharma Inc.	2018-10-01	Not applicable
Desonate	Gel	0.5 mg/1g	Topical	Intendis Inc.	2010-01-28	Not applicable
Desonide	Cream	0.5 mg/1g	Topical	Physicians Total Care, Inc.	2006-04-11	Not applicable
Desonide	Cream	0.5 mg/1g	Topical	Perrigo New York Inc	2006-04-11	Not applicable
Desonide	Cream	0.5 mg/1g	Topical	Rebel Distributors	2006-04-11	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Desonide	Cream	0.5 mg/1g	Topical	Gw Pharmaceuticals Ltd.	2016-08-19	Not applicable
Desonide	Lotion	0.5 mg/1mL	Topical	Glenmark Pharmaceuticals Inc.,Usa	2017-09-26	Not applicable
Desonide	Ointment	0.5 mg/1g	Topical	Glenmark Pharmaceuticals Inc., USA	2017-09-15	Not applicable
Desonide	Cream	0.5 mg/1g	Topical	Rebel Distributors	1992-06-30	Not applicable
Desonide	Cream	0.5 mg/1g	Topical	Taro Pharmaceuticals U.S.A., Inc.	1992-06-30	Not applicable
Desonide	Lotion	0.5 mg/1mL	Topical	E. Fougera & CO., A division of Fougera Pharmaceuticals Inc.	2002-03-19	Not applicable
Desonide	Ointment	0.5 mg/1g	Topical	North Star Rx Llc	2017-09-15	Not applicable
Desonide	Lotion	0.5 mg/1g	Topical	Physicians Total Care, Inc.	2004-05-17	Not applicable
Desonide	Lotion	.5 mg/1g	Topical	Owen Laboratories	1984-12-14	Not applicable
Desonide	Lotion	0.5 mg/1mL	Topical	Actavis Pharma Company	2009-05-28	Not applicable

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[10.8.0.0^{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

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.

Target	Actions	Organism
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

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

S01BA11 — Desonide

D07AB08 — Desonide

D07BB02 — Desonide and antiseptics

AHFS Codes

84:06.00 — Anti-inflammatory Agents

MSDS

Download (73.7 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Vasoconstriction	1
1	Recruiting	Basic Science	Healthy Volunteers	1
3	Completed	Treatment	Atopic Dermatitis (AD)	1
3	Completed	Treatment	Atopic Dermatitis Eczema	1
3	Unknown Status	Treatment	Atopic Dermatitis (AD) / Dermatitis, Eczematous	1
4	Completed	Treatment	Atopic Dermatitis (AD)	2
4	Completed	Treatment	Atopic Dermatitis (AD) / Dermatitis, Eczematous	1
4	Completed	Treatment	Hyperpigmentation	1
4	Not Yet Recruiting	Treatment	Psoriasis	1

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

Form	Route	Strength
Lotion	Topical	.05 %
Gel	Topical	0.5 mg/1g
Cream	Topical	.5 mg/1g
Lotion	Topical	.5 mg/1g
Lotion	Topical	0.5 mg/1g
Ointment	Topical	0.5 mg/1g
Cream	Topical	0.5 mg/1g
Lotion	Topical	0.5 mg/1mL
Cream	Topical	0.05 %
Ointment	Topical	0.05 %
Cream	Topical	.05 %
Ointment	Topical	.05 %
Cream	Topical	0.03 g/60g
Cream	Topical	.5 mg
Ointment	Topical	.5 mg
Aerosol, foam	Topical	0.05 %
Aerosol, foam	Topical	0.5 mg/1g

Prices

Unit description	Cost	Unit
DesOwen Lot w/Cetaphil Cream 0.05% Kit Box	255.84USD	box
Desowen 0.05% ointment kit	217.2USD	kit
Desowen 0.05% cream kit	212.4USD	kit
DesOwen 0.05% Lotion 118ml Bottle	183.17USD	bottle
Desonide powder	152.39USD	g
DesOwen 0.05% Lotion 59ml Bottle	123.38USD	bottle
Desonide 0.05% Lotion 118ml Bottle	76.75USD	bottle
Desonide 0.05% Lotion 59ml Bottle	50.86USD	bottle
Desonide 0.05% Ointment 60 gm Tube	41.76USD	tube
Desonide 0.05% Cream 60 gm Tube	41.48USD	tube
Desonide 0.05% Ointment 15 gm Tube	16.09USD	tube
Desonide 0.05% Cream 15 gm Tube	16.07USD	tube
Desowen 0.05% cream	2.43USD	g
Desonide 0.05% cream	0.81USD	g
Desocort 0.05 % Ointment	0.32USD	g
Pms-Desonide 0.05 % Cream	0.28USD	g
Pms-Desonide 0.05 % Ointment	0.28USD	g
Desocort 0.05 % Lotion	0.16USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US8460641	No	2013-06-11	2028-11-05
US8962000	No	2015-02-24	2025-08-31
US6730288	No	2004-05-04	2019-09-08
US7029659	No	2006-04-18	2019-09-08
US6387383	No	2002-05-14	2020-08-03
US9492384	No	2016-11-15	2025-08-31

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	257-260	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.
water solubility	Practically insoluble	Not Available
logP	1.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0594 mg/mL	ALOGPS
logP	2.31	ALOGPS
logP	1.9	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	112.06 m³·mol^-1	ChemAxon
Polarizability	44.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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 inhibitor	Non-inhibitor	0.8729
CYP450 2D6 inhibitor	Non-inhibitor	0.9544
CYP450 2C19 inhibitor	Non-inhibitor	0.9521
CYP450 3A4 inhibitor	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not 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

Details1. Glucocorticoid receptor

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

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]
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]
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

Details1. Cytochrome P450 3A4

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

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]
Verdeso monograph [File]

Drug created on May 16, 2007 11:31 / Updated on January 22, 2019 17:57

Desonide

Identification

Structure for Desonide (DB01260)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

Enzymes

References