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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
SaltsNot Available
Brand names
NameCompany
Espersonsanofi-aventis
Flubasonsanofi-aventis
Topicortsanofi-aventis
Topicort LPsanofi-aventis
Topisolonsanofi-aventis
Brand mixtures
Brand NameIngredients
DenomixDesoximetasone and Neomycin
Esperson NDesoximetasone and Neomycin
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[8.7.0.0^{2,7}.0^{11,15}]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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Halogenated Steroids; Ketosteroids; Iridoids and Derivatives; Cyclohexanols; Ketones; Cyclic Alcohols and Derivatives; Fluorohydrins; Primary Alcohols; Enolates; Polyamines; Organofluorides; Alkyl Fluorides; Aldehydes
Substituents3-keto-steroid; 20-keto-steroid; 9-halo-steroid; 11-hydroxy-steroid; 11-noriridane monoterpene; monoterpene; cyclohexanol; cyclic alcohol; secondary alcohol; ketone; halohydrin; fluorohydrin; polyamine; enolate; primary alcohol; alcohol; organofluoride; organohalogen; carbonyl group; alkyl halide; alkyl fluoride; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
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
Property Value Probability
Human Intestinal Absorption + 0.9928
Blood Brain Barrier + 0.9825
Caco-2 permeable + 0.9022
P-glycoprotein substrate Substrate 0.7712
P-glycoprotein inhibitor I Non-inhibitor 0.7281
P-glycoprotein inhibitor II Non-inhibitor 0.7049
Renal organic cation transporter Non-inhibitor 0.7676
CYP450 2C9 substrate Non-substrate 0.8621
CYP450 2D6 substrate Non-substrate 0.9066
CYP450 3A4 substrate Substrate 0.7565
CYP450 1A2 substrate Non-inhibitor 0.927
CYP450 2C9 substrate Non-inhibitor 0.9028
CYP450 2D6 substrate Non-inhibitor 0.8847
CYP450 2C19 substrate Non-inhibitor 0.9486
CYP450 3A4 substrate Non-inhibitor 0.6179
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8969
Ames test Non AMES toxic 0.9138
Carcinogenicity Non-carcinogens 0.9264
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 1.6856 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9473
hERG inhibition (predictor II) Inhibitor 0.5842
Pharmacoeconomics
Manufacturers
  • Nycomed us inc
  • Perrigo new york inc
  • Taro pharmaceuticals inc
  • Taro pharmaceuticals north america inc
  • Altana inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical
GelTopical
OintmentTopical
Prices
Unit descriptionCostUnit
Topicort 0.25% Ointment 60 gm Tube312.62USDtube
Topicort 0.25% Cream 60 gm Tube230.24USDtube
Desoximetasone 0.25% Ointment 60 gm Tube229.01USDtube
Desoximetasone 0.25% Cream 60 gm Tube204.91USDtube
Desoximetasone 0.05% Cream 60 gm Tube189.99USDtube
Desoximetasone 0.05% Gel 60 gm Tube174.86USDtube
Topicort 0.25% Ointment 15 gm Tube94.14USDtube
Topicort 0.05% Gel 15 gm Tube74.59USDtube
Desoximetasone 0.25% Ointment 15 gm Tube68.86USDtube
Topicort 0.25% Cream 15 gm Tube64.99USDtube
Desoximetasone 0.25% Cream 15 gm Tube59.94USDtube
Desoximetasone 0.05% Gel 15 gm Tube54.46USDtube
Desoximetasone 0.05% Cream 15 gm Tube51.25USDtube
Topicort 0.25% cream4.32USDg
Topicort lp 0.05% cream3.45USDg
Desoximetasone 0.05% cream1.29USDg
Topicort 0.25 % Cream0.73USDg
Desoximetasone 0.25% cream0.63USDg
Topicort Mild 0.05 % Cream0.5USDg
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 Solubility0.031ALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
ResourceLink
PubChem Compound5311067
PubChem Substance46506793
ChemSpider4470604
ChEBI691037
ChEMBLCHEMBL1766
Therapeutic Targets DatabaseDAP001185
PharmGKBPA164746011
Drug Product Database2241887
RxListhttp://www.rxlist.com/cgi/generic3/desoximeta.htm
Drugs.comhttp://www.drugs.com/cdi/desoximetasone-cream.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/top1452.shtml
WikipediaDesoximetasone
ATC CodesD07AC03D07XC02
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelshow(93.9 KB)
MSDSNot Available
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. 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