- Accession Number
- DB00547 (APRD00910)
- Small Molecule
A topical anti-inflammatory glucocorticoid used in dermatoses, skin allergies, psoriasis, etc. [PubChem]
- External IDs
- A-41-304 / Hoe 304 / HOE-304 / J83.644C / R 2113 / R-2113
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Desoxi Cream 0.05% Cream 0.05 % Topical Taropharma, A Division Of Taro Pharmaceuticals Inc. 1999-12-22 Not applicable Desoxi Cream 0.25% Cream 0.25 % Topical Taropharma, A Division Of Taro Pharmaceuticals Inc. 1999-12-22 Not applicable Desoxi Gel 0.05% Gel 0.05 % Topical Taropharma, A Division Of Taro Pharmaceuticals Inc. 2000-04-13 Not applicable Desoximetasone Ointment 0.5 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 1985-01-17 Not applicable Topicort Ointment 0.5 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 1985-01-17 Not applicable Topicort Cream 0.25 % Topical Valeant Canada Lp Valeant Canada S.E.C. 1997-03-24 Not applicable Topicort Spray 2.5 mg/1mL Topical Taro Pharmaceuticals U.S.A., Inc. 2013-04-11 Not applicable Topicort 0.25% Cream .25 % Topical Hoechst Canada Inc. 1977-12-31 1996-08-29 Topicort Crm 2.5mg/gm Cream 2.5 mg Topical Hoechst Roussel Canada Inc. 1994-12-31 1998-08-12 Topicort Gel Gel 0.05 % Topical Valeant Canada Lp Valeant Canada S.E.C. 1996-12-04 Not applicable
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Desoximetasone Ointment 2.5 mg/1g Topical Glenmark Pharmaceuticals Inc.,Usa 2013-09-20 Not applicable Desoximetasone Ointment 2.5 mg/1g Topical Zydus Pharmaceuticals Usa, Inc. 2017-12-05 Not applicable Desoximetasone Ointment 2.5 mg/1g Topical Physicians Total Care, Inc. 2008-05-08 Not applicable Desoximetasone Spray 2.5 mg/1mL Topical Taro Pharmaceuticals U.S.A., Inc. 2013-04-11 Not applicable Desoximetasone Ointment 2.5 mg/1g Topical Novel Laboratories, Inc. 2016-05-10 Not applicable Desoximetasone Gel 0.5 mg/1g Topical Rising Pharmaceuticals 2016-08-12 Not applicable Desoximetasone Cream 0.5 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 1990-11-30 Not applicable Desoximetasone Ointment 2.5 mg/1g Topical Versa Pharm Incorporated 2014-09-12 Not applicable Desoximetasone Cream 0.5 mg/1g Topical Versa Pharm Incorporated 2017-01-19 Not applicable Desoximetasone Cream 2.5 mg/1g Topical Versa Pharm Incorporated 2015-06-30 Not applicable
- International/Other Brands
- Esperson (sanofi-aventis) / Flubason (sanofi-aventis) / Topicort LP (sanofi-aventis) / Topisolon (sanofi-aventis)
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Steroids, Fluorinated
- CAS number
- Average: 376.4617
- Chemical Formula
- InChI Key
- IUPAC Name
For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
- Associated Conditions
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.
Target Actions Organism AGlucocorticoid receptoragonist Human
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.
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.
- Not Available
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
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- Drug Interactions
Drug Interaction (4R)-limonene The risk or severity of adverse effects can be increased when (4R)-limonene is combined with Desoximetasone. 1,10-Phenanthroline The risk or severity of adverse effects can be increased when Desoximetasone is combined with 1,10-Phenanthroline. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Desoximetasone. Acemetacin The risk or severity of adverse effects can be increased when Acemetacin is combined with Desoximetasone. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Desoximetasone. Adalimumab The risk or severity of adverse effects can be increased when Adalimumab is combined with Desoximetasone. Alclofenac The risk or severity of adverse effects can be increased when Alclofenac is combined with Desoximetasone. Alclometasone The risk or severity of adverse effects can be increased when Alclometasone is combined with Desoximetasone. Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Desoximetasone. Alemtuzumab The risk or severity of adverse effects can be increased when Alemtuzumab is combined with Desoximetasone.
- Food Interactions
- Not Available
- 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
- ATC Codes
- D07XC02 — Desoximetasone
- D07XC — Corticosteroids, potent, other combinations
- D07X — CORTICOSTEROIDS, OTHER COMBINATIONS
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- AHFS Codes
- 84:06.00 — Anti-inflammatory Agents
- FDA label
- Download (93.9 KB)
- Clinical Trials
Phase Status Purpose Conditions Count 3 Not Yet Recruiting Treatment Scalp Psoriasis 1 4 Recruiting Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1
- Nycomed us inc
- Perrigo new york inc
- Taro pharmaceuticals inc
- Taro pharmaceuticals north america inc
- Altana inc
- Dispensing Solutions
- E. Fougera and Co.
- Major Pharmaceuticals
- Nycomed Inc.
- Perrigo Co.
- Physicians Total Care Inc.
- Prescript Pharmaceuticals
- Sanofi-Aventis Inc.
- Taro Pharmaceuticals USA
- United Research Laboratories Inc.
- Dosage forms
Form Route Strength Cream Topical 0.5 mg/1g Cream Topical 2.5 mg/1g Gel Topical 0.5 mg/1g Cream Topical 0.25 % Ointment Topical 0.5 mg/1g Ointment Topical 2.5 mg/1g Spray Topical 2.5 mg/1mL Cream Topical .25 % Cream Topical 2.5 mg Gel Topical 0.05 % Gel Topical .05 % Gel Topical .5 mg Cream Topical 0.05 % Cream Topical .05 % Cream Topical .5 mg Ointment Topical 0.25 % Ointment Topical 2.5 mg
Unit description Cost Unit Topicort 0.25% Ointment 60 gm Tube 312.62USD tube Topicort 0.25% Cream 60 gm Tube 230.24USD tube Desoximetasone 0.25% Ointment 60 gm Tube 229.01USD tube Desoximetasone 0.25% Cream 60 gm Tube 204.91USD tube Desoximetasone 0.05% Cream 60 gm Tube 189.99USD tube Desoximetasone 0.05% Gel 60 gm Tube 174.86USD tube Topicort 0.25% Ointment 15 gm Tube 94.14USD tube Topicort 0.05% Gel 15 gm Tube 74.59USD tube Desoximetasone 0.25% Ointment 15 gm Tube 68.86USD tube Topicort 0.25% Cream 15 gm Tube 64.99USD tube Desoximetasone 0.25% Cream 15 gm Tube 59.94USD tube Desoximetasone 0.05% Gel 15 gm Tube 54.46USD tube Desoximetasone 0.05% Cream 15 gm Tube 51.25USD tube Topicort 0.25% cream 4.32USD g Topicort lp 0.05% cream 3.45USD g Desoximetasone 0.05% cream 1.29USD g Topicort 0.25 % Cream 0.73USD g Desoximetasone 0.25% cream 0.63USD g Topicort Mild 0.05 % Cream 0.5USD gDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent Number Pediatric Extension Approved Expires (estimated) US5990100 No 1998-03-24 2018-03-24 US8715624 No 2006-05-26 2026-05-26 US8277780 No 2008-09-01 2028-09-01
- Experimental Properties
Property Value Source melting point (°C) 217 °C PhysProp water solubility 42.1 mg/L Not Available logP 2.35 HANSCH,C ET AL. (1995)
- Predicted Properties
Property Value Source Water Solubility 0.031 mg/mL ALOGPS logP 2.13 ALOGPS logP 2.35 ChemAxon logS -4.1 ALOGPS pKa (Strongest Acidic) 13.44 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 101.17 m3·mol-1 ChemAxon Polarizability 40.09 Å3 ChemAxon Number of Rings 4 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 + 0.9928 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 inhibitor Non-inhibitor 0.9028 CYP450 2D6 inhibitor Non-inhibitor 0.8847 CYP450 2C19 inhibitor Non-inhibitor 0.9486 CYP450 3A4 inhibitor 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
- Mass Spec (NIST)
- Not Available
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 LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-000i-0859000000-a10700f328db7dc715b5 MS/MS Spectrum - , positive LC-MS/MS splash10-00di-2940000000-d3344c1ae6eb70791755
- 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.
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Steroids and steroid derivatives
- Sub Class
- Direct Parent
- 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 ketonesFluorohydrins / Organic oxides / Primary alcohols / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides show 6 more
- 21-hydroxysteroid / Progestogin-skeleton / 20-oxosteroid / Pregnane-skeleton / 9-halo-steroid / Halo-steroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Oxosteroid / 11-beta-hydroxysteroid11-hydroxysteroid / Delta-1,4-steroid / Alpha-hydroxy ketone / Cyclic alcohol / Ketone / Secondary alcohol / Halohydrin / Fluorohydrin / Cyclic ketone / Organic oxygen compound / Organohalogen compound / Organofluoride / Organooxygen compound / Primary alcohol / Carbonyl group / Hydrocarbon derivative / Alkyl halide / Alkyl fluoride / Alcohol / Organic oxide / Aliphatic homopolycyclic compound 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)
- Pharmacological action
- 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
- Uniprot ID
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
- 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]
- 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]
- 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]
- Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. [PubMed:16980198]
- 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]
- 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 September 21, 2018 00:02