Clobetasone

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
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
Medicalerrors
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Toxicity

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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Clobetasone can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hyperglycemia can be increased when Clobetasone is combined with Acarbose.
AcetohexamideThe risk or severity of hyperglycemia can be increased when Clobetasone is combined with Acetohexamide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Clobetasone is combined with Acetyldigitoxin.
AlbiglutideThe risk or severity of hyperglycemia can be increased when Clobetasone is combined with Albiglutide.
AlogliptinThe risk or severity of hyperglycemia can be increased when Clobetasone is combined with Alogliptin.
AminoglutethimideThe therapeutic efficacy of Clobetasone can be decreased when used in combination with Aminoglutethimide.
Bacillus calmette-guerin substrain russian BCG-I live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Clobetasone.
BendroflumethiazideThe risk or severity of electrolyte imbalance can be increased when Clobetasone is combined with Bendroflumethiazide.
BenzthiazideThe risk or severity of electrolyte imbalance can be increased when Clobetasone is combined with Benzthiazide.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Clobetasone butyrate8U0H6XI6EO25122-57-0FBRAWBYQGRLCEK-AVVSTMBFSA-N
International/Other Brands
Eumosone (GlaxoSmithKline)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EumovateOintment0.05 %TopicalGlaxosmithkline Inc2001-06-252007-08-02Canada flag
Eumovate Ont 0.05%Ointment0.05 %TopicalGlaxo Canada Inc1979-12-312001-08-01Canada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Eumovate Crm 0.05%Cream0.05 %TopicalGlaxo Canada Inc1979-12-312000-08-02Canada flag
Spectro Eczemacare Medicated CreamCream0.05 % w/wTopicalGlaxosmithkline Inc1999-09-27Not applicableCanada flag

Categories

ATC Codes
D07AB01 — ClobetasoneS01CA11 — Clobetasone and antiinfectivesS01BA09 — Clobetasone
Drug Categories
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
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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
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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
  1. Medsafe [Link]
  2. ChemIdplus [Link]
KEGG Drug
D07717
PubChem Compound
71387
PubChem Substance
347829268
ChemSpider
64482
RxNav
108074
ZINC
ZINC000005752185
Wikipedia
Clobetasone
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDermatitis, Eczematous1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamTopical
OintmentTopical
CreamTopical0.05 %
OintmentTopical0.05 %
CreamTopical0.05 % w/w
Solution / dropsOphthalmic
Suspension / dropsOphthalmic
OintmentTopical0.05 %w/w
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00691 mg/mLALOGPS
logP2.88ALOGPS
logP3.6ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.72 m3·mol-1ChemAxon
Polarizability41.36 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Targets

Drugtargets
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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
  1. UniProt [Link]
  2. KEGG [Link]

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
  1. Eumovate cream monograph [File]

Drug created on December 05, 2016 03:58 / Updated on May 15, 2021 12:14