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Identification
NameClobetasol propionate
Accession NumberDB01013  (APRD00876)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
21-chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-propionateNot AvailableNot Available
clobetasol 17-propanoateNot AvailableNot Available
clobetasol 17-propionateNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
ClobesolGlaxoSmithKline
ClobexGalderma
CormaxHi-Tech
DermovateGlaxoSmithKline
EmbelineHi-Tech
Embeline EHi-Tech
OluxMipharm
OLUX-ENot Available
TemovateFougera
Temovate EFougera
Brand mixturesNot Available
Categories
CAS number25122-46-7
WeightAverage: 466.97
Monoisotopic: 466.192230046
Chemical FormulaC25H32ClFO5
InChI KeyCBGUOGMQLZIXBE-KBUOYLHWNA-N
InChI
InChI=1/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-/s2
IUPAC Name
(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Halogenated Steroids; Iridoids and Derivatives; Cyclohexanols; Tertiary Alcohols; Cyclic Alcohols and Derivatives; Ketones; Fluorohydrins; Enolates; Polyamines; Organochlorides; Organofluorides; Alkyl Fluorides; Alkyl Chlorides
Substituents20-keto-steroid; 3-keto-steroid; 9-halo-steroid; 17-hydroxy-steroid; 11-hydroxy-steroid; monoterpene; 11-noriridane monoterpene; cyclohexanol; tertiary alcohol; cyclic alcohol; secondary alcohol; halohydrin; fluorohydrin; ketone; polyamine; enolate; organofluoride; organochloride; organohalogen; alcohol; carbonyl group; alkyl halide; alkyl fluoride; alkyl chloride
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationFor short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.
PharmacodynamicsLike 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 actionThe 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).
AbsorptionTopical 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 distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationCorticosteroids 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 lifeNot Available
ClearanceNot Available
ToxicityOral 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9814
Caco-2 permeable + 0.812
P-glycoprotein substrate Substrate 0.7852
P-glycoprotein inhibitor I Non-inhibitor 0.7375
P-glycoprotein inhibitor II Non-inhibitor 0.7683
Renal organic cation transporter Non-inhibitor 0.7883
CYP450 2C9 substrate Non-substrate 0.8533
CYP450 2D6 substrate Non-substrate 0.9077
CYP450 3A4 substrate Substrate 0.7967
CYP450 1A2 substrate Non-inhibitor 0.9412
CYP450 2C9 substrate Non-inhibitor 0.8713
CYP450 2D6 substrate Non-inhibitor 0.8327
CYP450 2C19 substrate Non-inhibitor 0.9126
CYP450 3A4 substrate Non-inhibitor 0.5411
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9129
Ames test Non AMES toxic 0.8848
Carcinogenicity Non-carcinogens 0.935
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.1435 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9314
hERG inhibition (predictor II) Non-inhibitor 0.5569
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
FormRouteStrength
CreamTopical
LiquidTopical
LotionTopical
OintmentTopical
ShampooTopical
SolutionTopical
Prices
Unit descriptionCostUnit
Clobex 0.05% Lotion 118ml Bottle513.56USDbottle
Clobex Spray 0.05% Liquid 125ml Bottle501.7USDbottle
Olux 0.05% Foam 100 gm Can443.77USDcan
Olux-E 0.05% Foam 100 gm Can384.32USDcan
Olux Olux-E Complete Pack 0.05 & 0.05% Miscellaneous 110 gm Can373.65USDcan
Clobex 0.05% Shampoo 118ml Bottle365.67USDbottle
Clobetasol Propionate 0.05% Foam 100 gm Can326.37USDcan
Clobex 0.05% Lotion 59ml Bottle280.8USDbottle
Clobex Spray 0.05% Liquid 59ml Bottle278.93USDbottle
Olux 0.05% Foam 50 gm Can239.07USDcan
Temovate 0.05% Cream 60 gm Tube234.19USDtube
Temovate 0.05% Gel 60 gm Tube234.19USDtube
Temovate E 0.05% Cream 60 gm Tube234.19USDtube
Clobetasol Propionate 0.05% Foam 50 gm Can177.05USDcan
Temovate 0.05% Ointment 30 gm Tube132.55USDtube
Temovate 0.05% Solution 50ml Bottle113.82USDbottle
Temovate 0.05% Cream 45 gm Tube95.43USDtube
Clobetasol Propionate 0.05% Gel 60 gm Tube93.82USDtube
Temovate 0.05% Ointment 15 gm Tube82.1USDtube
Clobetasol 17-prop powder70.74USDg
Clobetasol Propionate 0.05% Cream 60 gm Tube64.15USDtube
Clobetasol Propionate 0.05% Ointment 60 gm Tube64.15USDtube
Clobetasol Propionate 0.05% Gel 30 gm Tube51.66USDtube
Clobetasol Propionate 0.05% Ointment 45 gm Tube50.56USDtube
Clobetasol Propionate 0.05% Cream 45 gm Tube48.57USDtube
Temovate 0.05% Gel 15 gm Tube47.38USDtube
Temovate E 0.05% Cream 15 gm Tube44.9USDtube
Clobetasol Propionate 0.05% Solution 50ml Bottle41.18USDbottle
Clobetasol Propionate 0.05% Cream 30 gm Tube34.79USDtube
Clobetasol Propionate 0.05% Ointment 30 gm Tube34.79USDtube
Clobetasol Propionate 0.05% Gel 15 gm Tube28.86USDtube
Clobetasol Propionate 0.05% Solution 25ml Bottle26.99USDbottle
Clobetasol Propionate 0.05% Cream 15 gm Tube24.94USDtube
Clobetasol Propionate 0.05% Ointment 15 gm Tube24.1USDtube
Olux 0.05% foam6.77USDg
Olux-e 0.05% foam5.9USDg
Clobex 0.05% topical lotion4.58USDml
Temovate emollient 0.05% crm3.75USDg
Olux-olux-e complete pack3.43USDg
Temovate 0.05% cream3.29USDg
Cormax 0.05% cream2.06USDg
Embeline 0.05% cream1.86USDg
Clobetasol 0.05% cream1.43USDg
Dermovate 0.05 % Cream0.72USDg
Dermovate 0.05 % Ointment0.72USDg
Dermovate 0.05 % Lotion0.63USDg
Mylan-Clobetasol 0.05 % Cream0.38USDg
Mylan-Clobetasol 0.05 % Ointment0.38USDg
Novo-Clobetasol 0.05 % Cream0.38USDg
Novo-Clobetasol 0.05 % Ointment0.38USDg
Pms-Clobetasol 0.05 % Cream0.38USDg
Pms-Clobetasol 0.05 % Ointment0.38USDg
Ratio-Clobetasol 0.05 % Cream0.38USDg
Ratio-Clobetasol 0.05 % Ointment0.38USDg
Taro-Clobetasol 0.05 % Cream0.38USDg
Taro-Clobetasol 0.05 % Ointment0.38USDg
Mylan-Clobetasol 0.05 % Lotion0.33USDg
Pms-Clobetasol 0.05 % Lotion0.33USDg
Ratio-Clobetasol 0.05 % Lotion0.33USDg
Taro-Clobetasol 0.05 % Lotion0.33USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States77000812002-01-032022-01-03
United States61269201996-03-012016-03-01
Canada23338692009-01-062019-09-08
Canada23334272007-01-092019-06-17
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point226Elks, J., Phillipps, G.H. and May, P.J.; US. Patent 3,721,687; March 20, 1973; assigned to Glaxo Laboratories Limited, England.
water solubility3.86 mg/LNot Available
logP3.50SANGSTER (1994)
Predicted Properties
PropertyValueSource
water solubility4.13e-03 g/lALOGPS
logP3.49ALOGPS
logP4.18ChemAxon
logS-5ALOGPS
pKa (strongest acidic)13.63ChemAxon
pKa (strongest basic)-3.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area80.67ChemAxon
rotatable bond count5ChemAxon
refractivity119.32ChemAxon
polarizability48.28ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Elks, J., Phillipps, G.H. and May, P.J.; US. Patent 3,721,687; March 20, 1973; assigned to
Glaxo Laboratories Limited, England.

General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01272
ChEBI31414
ChEMBLCHEMBL1159650
Therapeutic Targets DatabaseDAP001183
PharmGKBPA164744375
Drug Product Database2245524
RxListhttp://www.rxlist.com/cgi/generic/olux.htm
Drugs.comhttp://www.drugs.com/cdi/clobetasol-cream.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/tem1431.shtml
WikipediaClobetasol_propionate
ATC CodesD07AD01
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelshow(95.3 KB)
MSDSshow(74.6 KB)
Interactions
Drug Interactions
Drug
AldesleukinCorticosteroids such as clobetasol may diminish the antineoplastic effect of aldesleukin. Avoid conccurent use of corticosteroids with aldesleukin.
TelaprevirCorticosteroids such as clobetasol may decrease the serum concentration of telaprevir. Telaprevir may increase the serum concentration of corticosteroids. Concurrent use of telaprevir and systemic corticosteroids is not recommended. When possible, consider alternatives, and if such a combination is necessary, use extra caution, monitoring patients for excessive systemic steroid effects as well as for diminished telaprevir effects.
Food InteractionsNot Available

Targets

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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
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Drug created on June 13, 2005 07:24 / Updated on April 07, 2014 15:10