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Identification
Name Clobetasol
Accession Number DB01013 (APRD00876)
Type small molecule
Groups approved
Description

A derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Clobesol
  • Clobetasol Propionate
  • Clobetasol propionate [USAN:JAN]
  • Clobetasole propionate
  • Clobetasolpropionat mikron.
  • Clobex
  • Dermovate
  • Embeline
  • Embeline E
  • Olux
  • Temovate
  • Temovate E
Brand name mixtures Not Available
Categories
  • Anti-inflammatory Agents
  • Corticosteroids, topical
  • Glucocorticoids
CAS number 25122-46-7
Weight Average: 466.97
Monoisotopic: 466.192230046
Chemical Formula C25H32ClFO5
InChI Key InChIKey=CBGUOGMQLZIXBE-XGQKBEPLSA-N
InChI
InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
Plain Text
IUPAC Name
(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
SMILES
[H][C@@]12C[C@H](C)[C@](OC(=O)CC)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Alkyl Halides
  • Ethers
  • Alcohols and Polyols
  • Ketones
Pharmacology
Indication For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.
Pharmacodynamics Like other topical corticosteroids, clobetasol has anti-inflammatory, antipruritic, and vasoconstrictive properties. It is a very high potency 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. 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. Initially, however, clobetasol, like other corticosteroids, bind to the glucocorticoid receptor, which complexes, enteres the cell nucleus and modifies genetic transcription (transrepression/transactivation).
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 Not Available
Metabolism

Metabolized, primarily in the liver, and then excreted by the kidneys.
Route of elimination Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids, including clobetasol propionate and its metabolites, are also excreted into the bile.
Half life Not Available
Clearance Not Available
Toxicity Oral LD50 in rat and mouse is >3000 mg/kg. Topically applied clobetasol 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
Pharmacoeconomics
Manufacturers
  • Perrigo israel pharmaceuticals ltd
  • Connetics corp
  • Stiefel laboratories inc
  • Actavis mid atlantic llc
  • E fougera div altana inc
  • Taro pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Altana inc
  • Stiefel a gsk co
  • Taro pharmaceuticals usa inc
  • Hi tech pharmacal co inc
  • Perrigo co
  • Galderma laboratories l p
  • Nycomed us inc
  • Galderma laboratories inc
  • Tolmar inc
  • Wockhardt eu operations (swiss) ag
  • Galderma laboratories lp
Packagers
Dosage forms
Form Route Strength
Cream Topical
Liquid Topical
Lotion Topical
Ointment Topical
Shampoo Topical
Solution Topical
Prices
Unit description Cost Unit
Clobex 0.05% Lotion 118ml Bottle 513.56 USD bottle
Clobex Spray 0.05% Liquid 125ml Bottle 501.7 USD bottle
Olux 0.05% Foam 100 gm Can 443.77 USD can
Olux-E 0.05% Foam 100 gm Can 384.32 USD can
Olux Olux-E Complete Pack 0.05 & 0.05% Miscellaneous 110 gm Can 373.65 USD can
Clobex 0.05% Shampoo 118ml Bottle 365.67 USD bottle
Clobetasol Propionate 0.05% Foam 100 gm Can 326.37 USD can
Clobex 0.05% Lotion 59ml Bottle 280.8 USD bottle
Clobex Spray 0.05% Liquid 59ml Bottle 278.93 USD bottle
Olux 0.05% Foam 50 gm Can 239.07 USD can
Temovate 0.05% Cream 60 gm Tube 234.19 USD tube
Temovate 0.05% Gel 60 gm Tube 234.19 USD tube
Temovate E 0.05% Cream 60 gm Tube 234.19 USD tube
Clobetasol Propionate 0.05% Foam 50 gm Can 177.05 USD can
Temovate 0.05% Ointment 30 gm Tube 132.55 USD tube
Temovate 0.05% Solution 50ml Bottle 113.82 USD bottle
Temovate 0.05% Cream 45 gm Tube 95.43 USD tube
Clobetasol Propionate 0.05% Gel 60 gm Tube 93.82 USD tube
Temovate 0.05% Ointment 15 gm Tube 82.1 USD tube
Clobetasol 17-prop powder 70.74 USD g
Clobetasol Propionate 0.05% Cream 60 gm Tube 64.15 USD tube
Clobetasol Propionate 0.05% Ointment 60 gm Tube 64.15 USD tube
Clobetasol Propionate 0.05% Gel 30 gm Tube 51.66 USD tube
Clobetasol Propionate 0.05% Ointment 45 gm Tube 50.56 USD tube
Clobetasol Propionate 0.05% Cream 45 gm Tube 48.57 USD tube
Temovate 0.05% Gel 15 gm Tube 47.38 USD tube
Temovate E 0.05% Cream 15 gm Tube 44.9 USD tube
Clobetasol Propionate 0.05% Solution 50ml Bottle 41.18 USD bottle
Clobetasol Propionate 0.05% Cream 30 gm Tube 34.79 USD tube
Clobetasol Propionate 0.05% Ointment 30 gm Tube 34.79 USD tube
Clobetasol Propionate 0.05% Gel 15 gm Tube 28.86 USD tube
Clobetasol Propionate 0.05% Solution 25ml Bottle 26.99 USD bottle
Clobetasol Propionate 0.05% Cream 15 gm Tube 24.94 USD tube
Clobetasol Propionate 0.05% Ointment 15 gm Tube 24.1 USD tube
Olux 0.05% foam 6.77 USD g
Olux-e 0.05% foam 5.9 USD g
Clobex 0.05% topical lotion 4.58 USD ml
Temovate emollient 0.05% crm 3.75 USD g
Olux-olux-e complete pack 3.43 USD g
Temovate 0.05% cream 3.29 USD g
Cormax 0.05% cream 2.06 USD g
Embeline 0.05% cream 1.86 USD g
Clobetasol 0.05% cream 1.43 USD g
Dermovate 0.05 % Cream 0.72 USD g
Dermovate 0.05 % Ointment 0.72 USD g
Dermovate 0.05 % Lotion 0.63 USD g
Mylan-Clobetasol 0.05 % Cream 0.38 USD g
Mylan-Clobetasol 0.05 % Ointment 0.38 USD g
Novo-Clobetasol 0.05 % Cream 0.38 USD g
Novo-Clobetasol 0.05 % Ointment 0.38 USD g
Pms-Clobetasol 0.05 % Cream 0.38 USD g
Pms-Clobetasol 0.05 % Ointment 0.38 USD g
Ratio-Clobetasol 0.05 % Cream 0.38 USD g
Ratio-Clobetasol 0.05 % Ointment 0.38 USD g
Taro-Clobetasol 0.05 % Cream 0.38 USD g
Taro-Clobetasol 0.05 % Ointment 0.38 USD g
Mylan-Clobetasol 0.05 % Lotion 0.33 USD g
Pms-Clobetasol 0.05 % Lotion 0.33 USD g
Ratio-Clobetasol 0.05 % Lotion 0.33 USD g
Taro-Clobetasol 0.05 % Lotion 0.33 USD g
Patents
Country Patent Number Approved Expires
United States 7700081 2002-01-03 2022-01-03
United States 6126920 1996-03-01 2016-03-01
Canada 2333869 2009-01-06 2019-09-08
Canada 2333427 2007-01-09 2019-06-17
Properties
State solid
Melting point 195.5-197 oC
Experimental Properties
Property Value Source
water solubility 3.86 mg/L PhysProp
logP 3 PhysProp
Predicted Properties
Property Value Source
water solubility 4.13e-03 g/l ALOGPS
logP 3.49 ALOGPS
logP 4.18 ChemAxon Molconvert
logS -5.05 ALOGPS
pKa 15.14 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 80.67 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 119.32 ChemAxon Molconvert
polarizability 47.87 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01272 Link_out
PubChem Compound 32798 Link_out
PubChem Substance 46505670 Link_out
ChemSpider 30399 Link_out
ChEBI 205919 Link_out
ChEMBL 205919 Link_out
Therapeutic Targets Database DAP001183 Link_out
PharmGKB PA449040 Link_out
Drug Product Database 2245524 Link_out
RxList http://www.rxlist.com/cgi/generic/olux.htm Link_out
Drugs.com http://www.drugs.com/cdi/clobetasol-cream.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/tem1431.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Clobetasol Link_out
ATC Codes
  • D07AD01
AHFS Codes
  • 84:06.00
PDB Entries Not Available
FDA label show (95.3 KB)
MSDS show (74.6 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Fitzgerald P, O’Brien SM, Scully P, Rijkers K, Scott LV, Dinan TG: Cutaneous glucocorticoid receptor sensitivity and pro-inflammatory cytokine levels in antidepressant-resistant depression. Psychol Med. 2006 Jan;36(1):37-43. Epub 2005 Oct 28. Pubmed
  2. Hofmann TG, Hehner SP, Bacher S, Droge W, Schmitz ML: Various glucocorticoids differ in their ability to induce gene expression, apoptosis and to repress NF-kappaB-dependent transcription. FEBS Lett. 1998 Dec 28;441(3):441-6. Pubmed
Enzymes

1. Cytochrome P450 1A1

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:07

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.