Identification
- Summary
Clobetasone is a corticosteroid used to treat dry eyes, eczema, and dermatitis.
- Generic Name
- Clobetasone
- DrugBank Accession Number
- DB13158
- Background
Clobetasone is a corticosteroid that is often employed topically as a treatment for a variety of conditions such as eczema, psoriasis, various forms of dermatitis, and also for certain ophthalmologic conditions. Topical clobetasone butyrate has shown minimal suppression of the Hypothalamic-pituitary-adrenal axis.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Clobetasone (DB13158)
- Weight
- Average: 408.89
Monoisotopic: 408.1503652 - Chemical Formula
- C22H26ClFO4
- Synonyms
- Clobetasona
- Clobetasone
Pharmacology
- Indication
In dermatology, topical clobestasone butyrate helps to reduce the itchiness and erythema associated with eczema and dermatitis. In ophthalmology, clobetasone butyrate 0.1% eye drops have been shown to be safe and effective in the treatment of dry eyes in Sjögren's Syndrome.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Allergic contact dermatitis ••• ••• Used in combination to treat Conjunctivitis allergic Combination Product in combination with: Tetryzoline (DB06764) •••••••••••• Symptomatic treatment of Conjunctivitis allergic •••••••••••• •••••••• • ••••• Symptomatic treatment of Cyclitis •••••••••••• •••••••• • ••••• Management of Eczema ••• ••• - Contraindications & Blackbox Warnings
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Topical corticosteroid like clobetasone are synthetic derivatives of cortisone which produce anti-inflammatory, antiproliferative, immunosuppressive and vasoconstrictor effects when applied to the skin.
- Mechanism of action
Topically applied clobeyasone are thought to bind with cytoplasmic receptors in the dermal and intradermal cells and to induce inhibitory proteins, thus leading to decreased activity of prostaglandins, kinins, histamine, liposomal enzymes and other endogenous mediators of inflammation. Topical corticosteroids inhibit the migration of macrophages and leukocytes into areas of inflamed skin by reversing vascular dilation and permeability, resulting in decreased erythema, edema and pruritus.
Target Actions Organism AGlucocorticoid receptor agonistHumans - Absorption
Absorption is dependent on many drug-related factors including: intrinsic properties of the steroid itself; concentration of the drug (increased concentration generally leads to more drug being absorbed but may plateau at higher concentrations); vehicle used (optimized or augmented vehicles > ointments or gels > creams or lotions); duration of exposure; frequency of application; combination with other products that break down the skin barrier and increase absorption (e.g., salicylic acid, urea). Patient-related factors that influence absorption include: patient age (infants and children absorb topical medications more quickly and to a greater degree than adults, and have a greater total skin surface to body weight ratio; the elderly have thinner skin and absorb drug more readily); disruption of the skin due to inflammation or disease (e.g., absorption increased in atopic dermatitis); total skin area treated; skin site treated (absorption is much greater from thin-skinned areas such as scalp, face, eyelid, axilla, and scrotum than from areas with thicker skin such as forearm, knee, elbow, palm and sole); absorption is increased with increased temperature or humidity of the skin or the environment; occlusion of the treated skin (via plastic wrap, oily vehicles, dressings, tape, diapers, tight-fitting clothing, etc.) can increase absorption up to 10-fold.
- Volume of distribution
The use of pharmacodynamic endpoints for assessing the systemic exposure of topical corticosteroids is necessary due to the fact that circulating levels are well below the level of detection.
- Protein binding
Not Available
- Metabolism
Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. They are metabolised, primarily in the liver.
- Route of elimination
Clobetasone and its metabolites are excreted in urine.
- Half-life
N/A
- Clearance
Not Available
- Adverse Effects
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Organism : Mouse Test type: LD50 Oral (Reported dose: >6gm/kg) LD50 Subcutaneous ( >3600mg/kg ) Effects : Behavioral : somnolence ( general depressed activity ) Blood changes in spleen
Organism : Mouse Test type: LD50 Route: Intraperitoneal Reported dose: 500 mg/kg
LD50 rat : 1510mg/kg Intraperitoneal LD50 rat >6gm/kg Oral LD 50 rat : > 2600mg/kg subcutaneous
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Clobetasone can be increased when it is combined with Abametapir. Acarbose The risk or severity of hyperglycemia can be increased when Clobetasone is combined with Acarbose. Acetohexamide The risk or severity of hyperglycemia can be increased when Clobetasone is combined with Acetohexamide. Acetyldigitoxin The risk or severity of adverse effects can be increased when Clobetasone is combined with Acetyldigitoxin. Albiglutide The risk or severity of hyperglycemia can be increased when Clobetasone is combined with Albiglutide. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Clobetasone butyrate 8U0H6XI6EO 25122-57-0 FBRAWBYQGRLCEK-AVVSTMBFSA-N - International/Other Brands
- Eumosone (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Eumovate Ointment 0.05 % Topical Glaxosmithkline Inc 2001-06-25 2007-08-02 Canada 
Eumovate Ont 0.05% Ointment 0.05 % Topical Glaxo Canada Inc 1979-12-31 2001-08-01 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Eumovate Crm 0.05% Cream 0.05 % Topical Glaxo Canada Inc 1979-12-31 2000-08-02 Canada Spectro Eczemacare Medicated Cream Cream 0.05 % w/w Topical Glaxosmithkline Inc 1999-09-27 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image VISUCLOBEN ANTIBIOTICO Clobetasone butyrate (1 MG/ML) + Bekanamycin (14.4 MG/ML) Suspension / drops Ophthalmic Visufarma S.P.A. 2014-07-08 2022-04-12 Italy 
Categories
- ATC Codes
- D07AB01 — Clobetasone
- D07AB — Corticosteroids, moderately potent (group II)
- D07A — CORTICOSTEROIDS, PLAIN
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- S01CA — Corticosteroids and antiinfectives in combination
- S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Moderately Potent (Group II)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs that are Mainly Renally Excreted
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Ointments
- Ophthalmologicals
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Sensory Organs
- Steroids
- Steroids, Fluorinated
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Pregnane steroids
- Direct Parent
- Gluco/mineralocorticoids, progestogins and derivatives
- Alternative Parents
- 20-oxosteroids / 11-oxosteroids / 17-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Alpha-chloroketones / Cyclic ketones show 7 more
- Substituents
- 11-oxosteroid / 17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl chloride / Alkyl fluoride show 21 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- LT69WY1J6D
- CAS number
- 54063-32-0
- InChI Key
- XXIFVOHLGBURIG-OZCCCYNHSA-N
- InChI
- InChI=1S/C22H26ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-16,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19-,20-,21-,22-/m0/s1
- IUPAC Name
- (1R,2S,10S,11S,13S,14R,15S)-14-(2-chloroacetyl)-1-fluoro-14-hydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione
- SMILES
- [H][C@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)C(=O)C[C@]2(C)[C@@]1(O)C(=O)CCl
References
- General References
- External Links
- KEGG Drug
- D07717
- PubChem Compound
- 71387
- PubChem Substance
- 347829268
- ChemSpider
- 64482
- 108074
- ZINC
- ZINC000005752185
- Wikipedia
- Clobetasone
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Atopic Dermatitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 0.05 % w/w Cream Topical Cream Topical 0.5 mg/g Cream Topical 0.5 mg Ointment Topical 0.5 MG/G Cream Topical 0.05 % Ointment Topical 0.05 % Cream Topical 0.05 %w/w Solution / drops Ophthalmic Suspension / drops Ophthalmic Ointment Topical 0.05 %w/w - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00691 mg/mL ALOGPS logP 2.88 ALOGPS logP 3.6 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 12.49 Chemaxon pKa (Strongest Basic) -3.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 71.44 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 104.72 m3·mol-1 Chemaxon Polarizability 41.36 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05g3-0009100000-82438b9045505425dd4c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0002900000-2bce86292e8ec5f46256 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-0449200000-a25b37d4a675fea47698 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-6009200000-bf7f1146abe96a216431 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0zgi-0009000000-d55a71b209f93ae47723 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0pi0-0390000000-01fd7ed6a651758cc421 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.71617 predictedDeepCCS 1.0 (2019) [M+H]+ 193.54106 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.14688 predictedDeepCCS 1.0 (2019)
Targets
- 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
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- 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
- Eumovate cream monograph [File]
Drug created at December 05, 2016 03:58 / Updated at February 20, 2024 23:55