Identification

Name
Desoximetasone
Accession Number
DB00547  (APRD00910)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • (11beta,16alpha)-9-Fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione
  • 9alpha-Fluoro-16alpha-methyl-delta(1)-corticosterone
  • Desoximetason
  • Desoximetasona
  • Désoximétasone
  • Desoximetasonum
  • Desoxymethasone
External IDs
A-41-304 / Hoe 304 / HOE-304 / J83.644C / R 2113 / R-2113
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desoxi Cream 0.05%Cream0.05 %TopicalTaropharma, A Division Of Taro Pharmaceuticals Inc.1999-12-22Not applicableCanada
Desoxi Cream 0.25%Cream0.25 %TopicalTaropharma, A Division Of Taro Pharmaceuticals Inc.1999-12-22Not applicableCanada
Desoxi Gel 0.05%Gel0.05 %TopicalTaropharma, A Division Of Taro Pharmaceuticals Inc.2000-04-13Not applicableCanada
DesoximetasoneOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.1985-01-17Not applicableUs
TopicortOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.1985-01-17Not applicableUs
TopicortCream0.25 %TopicalValeant Canada Lp Valeant Canada S.E.C.1997-03-24Not applicableCanada
TopicortSpray2.5 mg/1mLTopicalTaro Pharmaceuticals U.S.A., Inc.2013-04-11Not applicableUs
Topicort 0.25%Cream.25 %TopicalHoechst Canada Inc.1977-12-311996-08-29Canada
Topicort Crm 2.5mg/gmCream2.5 mgTopicalHoechst Roussel Canada Inc.1994-12-311998-08-12Canada
Topicort GelGel0.05 %TopicalValeant Canada Lp Valeant Canada S.E.C.1996-12-04Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DesoximetasoneOintment2.5 mg/1gTopicalActavis Pharma Company2016-11-21Not applicableUs
DesoximetasoneCream0.5 mg/1gTopicalVersaPharm Inc. - an Akorn Company2017-01-19Not applicableUs
DesoximetasoneOintment2.5 mg/1gTopicalPhysicians Total Care, Inc.2008-05-08Not applicableUs
DesoximetasoneCream2.5 mg/1gTopicalProficient Rx LP2006-10-24Not applicableUs
DesoximetasoneCream2.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.1990-11-30Not applicableUs
DesoximetasoneOintment2.5 mg/1gTopicalCadila Pharnmaceuticals2017-12-05Not applicableUs
DesoximetasoneSpray2.5 mg/1mLTopicalTaro Pharmaceuticals U.S.A., Inc.2013-04-11Not applicableUs
DesoximetasoneOintment2.5 mg/1gTopicalGw Pharmaceuticals Ltd.2016-09-01Not applicableUs
DesoximetasoneCream2.5 mg/1gTopicalActavis Pharma Company2016-03-31Not applicableUs
DesoximetasoneOintment2.5 mg/1gTopicalPerrigo New York Inc.2015-05-14Not applicableUs
International/Other Brands
Esperson (sanofi-aventis) / Flubason (sanofi-aventis) / Topicort LP (sanofi-aventis) / Topisolon (sanofi-aventis)
Categories
UNII
4E07GXB7AU
CAS number
382-67-2
Weight
Average: 376.4617
Monoisotopic: 376.204987621
Chemical Formula
C22H29FO4
InChI Key
VWVSBHGCDBMOOT-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

Pharmacology

Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Associated Conditions
Pharmacodynamics

Like 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 action

The 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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Human
Absorption

Topical 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 distribution
Not Available
Protein binding

Bound to plasma proteins in varying degrees.

Metabolism

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

Route of elimination

Corticosteroids 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 life

The half-life of the material was 15 ± 2 hours (for urine) and 17 ± 2 hours (for feces) between the third and fifth trial day.

Clearance
Not Available
Toxicity

Topically 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0014687
PubChem Compound
5311067
PubChem Substance
46506793
ChemSpider
4470604
ChEBI
691037
ChEMBL
CHEMBL1766
Therapeutic Targets Database
DAP001185
PharmGKB
PA164746011
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Desoximetasone
ATC Codes
D07XC02 — DesoximetasoneD07AC03 — Desoximetasone
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
FDA label
Download (93.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Not Yet RecruitingTreatmentScalp Psoriasis1
4RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1

Pharmacoeconomics

Manufacturers
  • Nycomed us inc
  • Perrigo new york inc
  • Taro pharmaceuticals inc
  • Taro pharmaceuticals north america inc
  • Altana inc
Packagers
  • Dispensing Solutions
  • E. Fougera and Co.
  • Major Pharmaceuticals
  • Nycomed Inc.
  • Perrigo Co.
  • Pharmedix
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
  • Qualitest
  • Sanofi-Aventis Inc.
  • Taro Pharmaceuticals USA
  • United Research Laboratories Inc.
Dosage forms
FormRouteStrength
CreamTopical0.5 mg/1g
CreamTopical2.5 mg/1g
GelTopical0.5 mg/1g
CreamTopical0.25 %
OintmentTopical0.5 mg/1g
OintmentTopical2.5 mg/1g
SprayTopical2.5 mg/1mL
CreamTopical.25 %
CreamTopical2.5 mg
GelTopical0.05 %
GelTopical.05 %
GelTopical.5 mg
CreamTopical0.05 %
CreamTopical.05 %
CreamTopical.5 mg
OintmentTopical0.25 %
OintmentTopical2.5 mg
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5990100No1999-11-232018-03-24Us
US8715624No2014-05-062026-05-26Us
US8277780No2012-10-022028-09-01Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)217 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.9028
CYP450 2D6 inhibitorNon-inhibitor0.8847
CYP450 2C19 inhibitorNon-inhibitor0.9486
CYP450 3A4 inhibitorNon-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
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0859000000-a10700f328db7dc715b5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-2940000000-d3344c1ae6eb70791755

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 / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Alpha-hydroxy ketones / Secondary alcohols / Cyclic alcohols and derivatives / Cyclic ketones
show 6 more
Substituents
21-hydroxysteroid / Progestogin-skeleton / 20-oxosteroid / Pregnane-skeleton / 9-halo-steroid / Halo-steroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Oxosteroid / 11-beta-hydroxysteroid
show 21 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
11beta-hydroxy steroid, glucocorticoid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (CHEBI:691037)

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. 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:10754457]
  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:16891588]
  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:16895953]
  4. Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. [PubMed:16980198]
  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:17038445]
  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:17086345]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2018 11:08