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Identification
NameDesoximetasone
Accession NumberDB00547  (APRD00910)
TypeSmall Molecule
GroupsApproved
Description

A topical anti-inflammatory glucocorticoid used in dermatoses, skin allergies, psoriasis, etc. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(11beta,16alpha)-9-Fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dioneNot AvailableNot Available
9alpha-Fluoro-16alpha-methyl-delta(1)-corticosteroneNot AvailableNot Available
DesoximetasonGermanINN
DesoximetasonaSpanishINN
DésoximétasoneFrenchINN
DesoximetasonumLatinINN
DesoxymethasoneNot AvailableIS
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desoximetasoneointment.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1985-01-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topicortointment.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1985-01-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topicortspray2.5 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.2013-04-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topicortcream0.25 %topicalValeant Canada Lp Valeant Canada S.E.C.Not AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desoximetasoneointment2.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2012-09-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonecream2.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2010-06-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonecream2.5 mg/gtopicalRebel Distributors Corp1990-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonecream2.5 mg/gtopicalPerrigo New York Inc2006-10-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonegel.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1998-07-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasoneointment2.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1996-06-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonecream2.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1990-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonecream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1990-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topicortgel.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1998-07-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topicortointment2.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1992-12-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topicortcream2.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1990-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topicortcream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1990-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonegel.5 mg/gtopicalPhysicians Total Care, Inc.2008-02-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonecream2.5 mg/gtopicalPhysicians Total Care, Inc.1994-06-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasoneointment2.5 mg/gtopicalPhysicians Total Care, Inc.2008-05-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasonegel.5 mg/gtopicalVersa Pharm Incorporated2011-04-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasoneointment2.5 mg/gtopicalVersa Pharm Incorporated2014-09-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Desoximetasoneointment2.5 mg/gtopicalGlenmark Generics Inc.,USA2013-09-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
Espersonsanofi-aventis
Flubasonsanofi-aventis
Topicort LPsanofi-aventis
Topisolonsanofi-aventis
Brand mixtures
Brand NameIngredients
DenomixDesoximetasone and Neomycin
Esperson NDesoximetasone and Neomycin
SaltsNot Available
CategoriesNot Available
CAS number382-67-2
WeightAverage: 376.4617
Monoisotopic: 376.204987621
Chemical FormulaC22H29FO4
InChI KeyVWVSBHGCDBMOOT-IIEHVVJPSA-N
InChI
InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
IUPAC Name
(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
SMILES
[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
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
  • Halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Halohydrin
  • Fluorohydrin
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
PharmacodynamicsLike other topical corticosteroids, desoximetasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Desoximetasone is a potent topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
Mechanism of actionThe precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. This is achieved first by the drug binding to the glucocorticoid receptors which then translocates into the nucleus and binds to DNA causing various activations and repressions of genes. 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 intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
Volume of distributionNot Available
Protein bindingBound to plasma proteins in varying degrees.
Metabolism

Metabolized, primarily in the liver, and then excreted by the kidneys.

Route of eliminationCorticosteroids are bound to plasma proteins in varying degrees, are metabolized primarily in the liver and excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.Pharmacokinetic studies in men with Desoximetasone Cream USP, 0.25% with tagged desoximetasone showed a total of 5.2% ± 2.9% excretion in urine (4.1% ± 2.3%) and feces (1.1% ± 0.6%)
Half lifeThe half-life of the material was 15 ± 2 hours (for urine) and 17 ± 2 hours (for feces) between the third and fifth trial day.
ClearanceNot Available
ToxicityTopically applied desoximetasone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
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+0.9928
Blood Brain Barrier+0.9825
Caco-2 permeable+0.9022
P-glycoprotein substrateSubstrate0.7712
P-glycoprotein inhibitor INon-inhibitor0.7281
P-glycoprotein inhibitor IINon-inhibitor0.7049
Renal organic cation transporterNon-inhibitor0.7676
CYP450 2C9 substrateNon-substrate0.8621
CYP450 2D6 substrateNon-substrate0.9066
CYP450 3A4 substrateSubstrate0.7565
CYP450 1A2 substrateNon-inhibitor0.927
CYP450 2C9 substrateNon-inhibitor0.9028
CYP450 2D6 substrateNon-inhibitor0.8847
CYP450 2C19 substrateNon-inhibitor0.9486
CYP450 3A4 substrateNon-inhibitor0.6179
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8969
Ames testNon AMES toxic0.9138
CarcinogenicityNon-carcinogens0.9264
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.6856 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9473
hERG inhibition (predictor II)Inhibitor0.5842
Pharmacoeconomics
Manufacturers
  • Nycomed us inc
  • Perrigo new york inc
  • Taro pharmaceuticals inc
  • Taro pharmaceuticals north america inc
  • Altana inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical.5 mg/g
Creamtopical0.25 %
Creamtopical2.5 mg/g
Geltopical.5 mg/g
Ointmenttopical.5 mg/g
Ointmenttopical2.5 mg/g
Spraytopical2.5 mg/mL
Prices
Unit descriptionCostUnit
Topicort 0.25% Ointment 60 gm Tube312.62USD tube
Topicort 0.25% Cream 60 gm Tube230.24USD tube
Desoximetasone 0.25% Ointment 60 gm Tube229.01USD tube
Desoximetasone 0.25% Cream 60 gm Tube204.91USD tube
Desoximetasone 0.05% Cream 60 gm Tube189.99USD tube
Desoximetasone 0.05% Gel 60 gm Tube174.86USD tube
Topicort 0.25% Ointment 15 gm Tube94.14USD tube
Topicort 0.05% Gel 15 gm Tube74.59USD tube
Desoximetasone 0.25% Ointment 15 gm Tube68.86USD tube
Topicort 0.25% Cream 15 gm Tube64.99USD tube
Desoximetasone 0.25% Cream 15 gm Tube59.94USD tube
Desoximetasone 0.05% Gel 15 gm Tube54.46USD tube
Desoximetasone 0.05% Cream 15 gm Tube51.25USD tube
Topicort 0.25% cream4.32USD g
Topicort lp 0.05% cream3.45USD g
Desoximetasone 0.05% cream1.29USD g
Topicort 0.25 % Cream0.73USD g
Desoximetasone 0.25% cream0.63USD g
Topicort Mild 0.05 % Cream0.5USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point217 °CPhysProp
water solubility42.1 mg/LNot Available
logP2.35HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.031 mg/mLALOGPS
logP2.13ALOGPS
logP2.35ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.44ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.17 m3·mol-1ChemAxon
Polarizability40.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Kieslich, K., Kerb, U. and Raspe, G.; U S . Patent 3,232,839; February 1,1966; assigned to
Schering AG, Germany.

General ReferenceNot Available
External Links
ATC CodesD07AC03D07XC02
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelDownload (93.9 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinCorticosteroids may diminish the antineoplastic effect of Aldesleukin.
DeferasiroxCorticosteroids may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
HyaluronidaseCorticosteroids may diminish the therapeutic effect of Hyaluronidase.
TelaprevirCorticosteroids may decrease the serum concentration of Telaprevir. Telaprevir may increase the serum concentration of Corticosteroids.
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. Lange K, Kleuser B, Gysler A, Bader M, Maia C, Scheidereit C, Korting HC, Schafer-Korting M: Cutaneous inflammation and proliferation in vitro: differential effects and mode of action of topical glucocorticoids. Skin Pharmacol Appl Skin Physiol. 2000 Mar-Apr;13(2):93-103. Pubmed
  2. Grossman R, Yehuda R, Golier J, McEwen B, Harvey P, Maria NS: Cognitive effects of intravenous hydrocortisone in subjects with PTSD and healthy control subjects. Ann N Y Acad Sci. 2006 Jul;1071:410-21. Pubmed
  3. Rautanen A, Eriksson JG, Kere J, Andersson S, Osmond C, Tienari P, Sairanen H, Barker DJ, Phillips DI, Forsen T, Kajantie E: Associations of body size at birth with late-life cortisol concentrations and glucose tolerance are modified by haplotypes of the glucocorticoid receptor gene. J Clin Endocrinol Metab. 2006 Nov;91(11):4544-51. Epub 2006 Aug 8. Pubmed
  4. Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. Pubmed
  5. 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
  6. Sher L: Combined dexamethasone suppression-corticotropin-releasing hormone stimulation test in studies of depression, alcoholism, and suicidal behavior. ScientificWorldJournal. 2006 Oct 31;6:1398-404. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 10, 2014 13:56