Clobetasol propionate

Identification

Summary

Clobetasol propionate is a corticosteroid used to treat corticosteroid-responsive dermatoses and plaque psoriasis.

Brand Names
Clobex, Clodan, Dermovate, Impeklo, Impoyz, Olux, Temovate, Tovet
Generic Name
Clobetasol propionate
DrugBank Accession Number
DB01013
Background

Clobetasol propionate is a prednisolone derivative with higher specificity for glucocorticoid receptors than mineralocorticoid receptors.10 It has demonstrated superior activity compared to fluocinonide4 and was first described in the literature in 1974.1

Clobetasol Propionate was granted FDA approval on 27 December 1985.9

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 466.97
Monoisotopic: 466.192230046
Chemical Formula
C25H32ClFO5
Synonyms
  • 21-chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-propionate
  • clobetasol 17-propanoate
  • clobetasol 17-propionate
  • Clobetasol propionate
  • Clobetasol propionate E
External IDs
  • CCI 4725
  • CCI-4725
  • GR 2/925
  • GR-2/925

Pharmacology

Indication

Clobetasol propionate is indicated to treat moderate to severe plaque psoriasis11,12,13 as well as inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.10,14

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAlopeciaCombination Product in combination with: Minoxidil (DB00350), Tretinoin (DB00755)••••••••••••••••••••
Treatment ofSevere plaque psoriasis•••••••••••••••••••• ••••• •••
Treatment ofSevere plaque psoriasis•••••••••••••••••
Treatment ofSevere plaque psoriasis•••••••••••••••••
Treatment ofCorticosteroid responsive, inflammatory dermatosis••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals.5 Clobetasol propionate is generally applied twice daily so the duration of action is long.10,11,12,13,14,15 Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces.5 Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.5

Mechanism of action

The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation.5 Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days.5

Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10.5

Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive.5 High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.5

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
UAnnexin A1
inducer
Humans
UMineralocorticoid receptor
agonist
Humans
Absorption

Twice daily application of clobetasol foam leads to a Cmax of 59±36pg/mL with a Tmax of 5 hours.10 Clobetasol cream showed an increase in clobetasol concentrations from 50.7±96.0pg/mL to 56.3±104.7pg/mL.12

Volume of distribution

Data regarding the volume of distribution of clobetasole propionate are not readily available.10,11,12,13,14,15

Protein binding

Data regarding the protein binding of clobetasol propionate are not readily available.10,11,12,13,14,15 Corticosteroids are generally bound to corticosteroid binding globulin6 and serum albumin7 in plasma.

Metabolism

The metabolism of clobetasol propionate is not well studied but it does induce metabolic enzymes, even when delivered topically.2 The metabolism of clobetasol propionate is predicted to follow similar metabolic pathways to other corticosteroids including the addition of oxygen, hydrogen, glucuronides, and sulfates to form water soluble metabolites.15

Route of elimination

Corticosteroids are eliminated predominantly in the urine.7

Half-life

Data regarding the half life of clobetasol propionate are not readily available.3

Clearance

Data regarding the clearance of clobetasol propionate are not readily available.3

Adverse Effects
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Toxicity

Data regarding acute overdoses of glucocorticoids are rare.10,11,12 Overdoses of clobetasol propionate can lead to reversible HPA axis suppression and glucocorticoid insufficiency.15 Chronic high doses of glucocorticoids can lead to the development of cataract, glaucoma, hypertension, water retention, hyperlipidemia, peptic ulcer, pancreatitis, myopathy, osteoporosis, mood changes, psychosis, dermal atrophy, allergy, acne, hypertrichosis, immune suppression, decreased resistance to infection, moon face, hyperglycemia, hypocalcemia, hypophosphatemia, metabolic acidosis, growth suppression, and secondary adrenal insufficiency.8 Overdose may be treated by adjusting the dose or stopping the corticosteroid as well as initiating symptomatic and supportive treatment.8

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 Clobetasol propionate can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Clobetasol propionate.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Clobetasol propionate.
AcarboseThe risk or severity of hyperglycemia can be increased when Clobetasol propionate is combined with Acarbose.
Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
ClobetasolprodrugADN79D536H25122-41-2FCSHDIVRCWTZOX-DVTGEIKXSA-N
International/Other Brands
Clobesol (GlaxoSmithKline) / Dermovate (GlaxoSmithKline) / Embeline (Hi-Tech) / Embeline E (Hi-Tech)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Clobetasol Cream 0.05%Cream0.05 %TopicalPrempharm Inc1996-12-232005-08-05Canada flag
Clobetasol Ointment 0.05%Ointment0.05 %TopicalPrempharm Inc1996-12-232005-08-05Canada flag
Clobetasol PropionateOintment0.5 mg/1gTopicalGlades Pharmaceuticals LLC2009-12-312010-01-01US flag
Clobetasol PropionateCream0.5 mg/1gTopicalStiefel Laboratories, Inc.2009-12-312010-01-01US flag
Clobetasol PropionateOintment0.5 mg/1gTopicalActavis Mid Atlantic LLC,2007-10-122007-10-19US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alti-clobetasol Propionate Cream 0.05%Cream.05 %TopicalAltimed Pharma Inc.1993-12-312001-09-05Canada flag
Alti-clobetasol Propionate Ont 0.05%Ointment.05 %TopicalAltimed Pharma Inc.1993-12-312001-09-05Canada flag
Alti-clobetasol Propionate Scalp Application 0.05%Liquid.05 %TopicalAltimed Pharma Inc.1993-12-312001-09-05Canada flag
Apo-clobetasol SpraySpray0.05 % w/wTopicalApotex Corporation2018-07-17Not applicableCanada flag
Clobetasol PropionateOintment0.5 mg/1gTopicalGlenmark Pharmaceuticals Inc., USA2017-03-20Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TACOSOL CREAMCream0.05 %w/wบริษัท วาย.เอส.พี. (ประเทศไทย) จำกัด2008-09-18Not applicableThailand flag
ฮอฟเวทCream0.05 %w/wบริษัท โอสถ อินเตอร์ แลบบอราทอรีส์ จำกัด จำกัด2008-11-20Not applicableThailand flag
โคลทาซอลCream0.05 %w/wบริษัท บูรพาโอสถ จำกัด จำกัด2000-12-19Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ClobetaClobetasol propionate (0.5 mg/1g) + Coal tar (23 mg/1mL)KitTopicalTiber Laboratories, LLC2011-04-062012-06-30US flag
ClobetaClobetasol propionate (0.5 mg/1g) + Coal tar (23 mg/1mL)KitTopicalTiber Laboratories, LLC2011-04-062012-06-30US flag
ClobetairClobetasol propionate (0.5 mg/1g) + Dimethicone (50 mg/1mL)KitTopicalPureTek Corporation2020-03-232020-05-21US flag
ClobetavixClobetasol propionate (0.5 mg/1g) + Clobetasol propionate (0.5 g/1g)KitTopicalPrimary Pharmaceuticals, Inc2019-01-23Not applicableUS flag
ClobetavixClobetasol propionate (0.5 mg/1g) + Clobetasol propionate (0.5 g/1g)KitTopicalPrimary Pharmaceuticals, Inc2019-01-23Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Calcipotriene 0.005% / Clobetasol Propionate 0.05%Clobetasol propionate (0.05 g/100g) + Calcipotriol (0.005 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-20Not applicableUS flag
Ciclopirox 1% / Clobetasol Propionate 0.05%Clobetasol propionate (0.05 g/100g) + Ciclopirox (1 g/100g)ShampooTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
Ciclopirox Olamine 0.77% / Clobetasol Propionate 0.05% / Salicylic Acid 3%.Clobetasol propionate (0.05 g/100g) + Ciclopirox olamine (1 g/100g) + Salicylic acid (3 g/100g)ShampooTopicalSincerus Florida, LLC2019-05-17Not applicableUS flag
Clobetasol Propionate 0.05% / Coal Tar 8% / Salicylic Acid 6%Clobetasol propionate (0.05 g/100g) + Coal tar (8 g/100g) + Salicylic acid (6 g/100g)CreamTopicalSincerus Florida, LLC2019-05-15Not applicableUS flag
Clobetasol Propionate 0.05% / Levocetirizine Dihydrochloride 2%Clobetasol propionate (0.05 g/100g) + Levocetirizine dihydrochloride (2 g/100g)ShampooTopicalSincerus Florida, LLC2019-05-17Not applicableUS flag

Categories

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
Steroid esters / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Alpha-acyloxy ketones / Alpha-chloroketones / Fluorohydrins / Cyclic ketones
show 10 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl chloride / Alkyl fluoride
show 27 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
11beta-hydroxy steroid, glucocorticoid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, chlorinated steroid (CHEBI:31414)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
779619577M
CAS number
25122-46-7
InChI Key
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
IUPAC Name
(1R,2S,3aS,3bS,9aS,9bR,10S,11aS)-1-(2-chloroacetyl)-9b-fluoro-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-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

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 References
  1. Sparkes CG, Wilson L: The clinical evaluation of a new topical corticosteroid, clobetasol propionate. An international controlled trial. Br J Dermatol. 1974 Feb;90(2):197-203. doi: 10.1111/j.1365-2133.1974.tb06385.x. [Article]
  2. Finnen MJ, Herdman ML, Shuster S: Induction of drug metabolising enzymes in the skin by topical steroids. J Steroid Biochem. 1984 May;20(5):1169-73. doi: 10.1016/0022-4731(84)90362-5. [Article]
  3. Hehir M, Du Vivier A, Eilon L, Danie MJ, Shenoy EV: Investigation of the pharmacokinetics of clobetasol propionate and clobetasone butyrate after a single application of ointment. Clin Exp Dermatol. 1983 Mar;8(2):143-51. doi: 10.1111/j.1365-2230.1983.tb01758.x. [Article]
  4. Jegasothy B, Jacobson C, Levine N, Millikan L, Olsen E, Pinnell S, Cole G, Weinstein G, Porter M: Clobetasol propionate versus fluocinonide creams in psoriasis and eczema. Int J Dermatol. 1985 Sep;24(7):461-5. doi: 10.1111/j.1365-4362.1985.tb05821.x. [Article]
  5. Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [Article]
  6. Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [Article]
  7. Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [Article]
  8. Ciriaco M, Ventrice P, Russo G, Scicchitano M, Mazzitello G, Scicchitano F, Russo E: Corticosteroid-related central nervous system side effects. J Pharmacol Pharmacother. 2013 Dec;4(Suppl 1):S94-8. doi: 10.4103/0976-500X.120975. [Article]
  9. FDA Approved Drug Products: Temovate Clobetasol Propionate Topical Cream (Discontinued) [Link]
  10. FDA Approved Drug Products: Olux-E Clobetasol Propionate Topical Aerosol Foam [Link]
  11. FDA Approved Drug Products: Olux Clobetasol Propionate Topical Aerosol Foam [Link]
  12. FDA Approved Drug Products: Impoyz Clobetasol Propionate Topical Cream [Link]
  13. FDA Approved Drug Products: Clobex Clobetasol Propionate Topical Spray [Link]
  14. FDA Approved Drug Products: Clobex Clobetasol Propionate Topical Lotion [Link]
  15. Health Canada Approved Drug Products: Clobetasol Propionate Topical Spray [Link]
KEGG Drug
D01272
PubChem Compound
32798
PubChem Substance
46505670
ChemSpider
30399
BindingDB
39347
RxNav
21245
ChEBI
31414
ChEMBL
CHEMBL1159650
ZINC
ZINC000003977767
Therapeutic Targets Database
DAP001183
PharmGKB
PA164744375
PDBe Ligand
XRD
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Clobetasol_propionate
PDB Entries
7lad
FDA label
Download (95.3 KB)
MSDS
Download (74.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAlopecia Areata (AA)1
4CompletedTreatmentChronic Stable Plaque Psoriasis1
4CompletedTreatmentDermatitis, Chronic1
4CompletedTreatmentHand Dermatosis1
4CompletedTreatmentPsoriasis6

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
  • Accra Pac Inc.
  • Ameri-Pac Inc.
  • A-S Medication Solutions LLC
  • Contract Pharm
  • Dermalogix
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DPT Laboratories Ltd.
  • E. Fougera and Co.
  • Galderma Laboratories
  • GlaxoSmithKline Inc.
  • Glenmark Generics Ltd.
  • Hi Tech Pharmacal Co. Inc.
  • Inyx Usa Ltd.
  • Nycomed Inc.
  • Palmetto Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharma Pac LLC
  • Pharmaderm
  • Pharmedix
  • Physicians Total Care Inc.
  • Prasco Labs
  • Preferred Pharmaceuticals Inc.
  • Quality Care
  • Rebel Distributors Corp.
  • Stat Rx Usa
  • Stiefel Labs
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
CreamTopical.05 %
LiquidTopical.05 %
CreamCutaneous
OintmentTopical0.5 mg/g
LotionTopical0.05 g
LotionOral0.05 g
AerosolTopical0.05 g
SolutionOral0.5 mg/g
OintmentTopical0.44 mg/g
ShampooTopical
Aerosol, foamTopical500 Mikrogramm/g
Aerosol, foamTopical500 UG/G
Aerosol, foamTopical500 mcg/g
EmulsionTopical0.05 g
ShampooTopical500 MICROGRAMMI/G
EmulsionTopical0.5 mg/g
CreamCutaneous0.05 %
CreamCutaneous0.05 g
OintmentCutaneous0.05 %
OintmentCutaneous20 G
OintmentTopical20 G
Cream0.05 %
KitTopical
Aerosol, foamTopical0.5 mg/1g
CreamTopical.5 mg/1g
CreamTopical0.5 mg/1g
EmulsionTopical0.5 mg/1g
GelTopical.05 mg/1g
GelTopical0.5 mg/1g
LotionTopical.05 mg/100mL
LotionTopical0.05 g/100mL
LotionTopical0.5 mg/1mL
OintmentTopical.5 mg/1g
OintmentTopical0.5 mg/1g
ShampooTopical.5 mg/1mL
SolutionTopical0.462 mg/1mL
SolutionTopical0.5 mg/1mL
SprayTopical0.05 g/1mL
CreamTopical
OintmentTopical
SolutionTopical
CreamTopical50 mg
SolutionTopical500 mcg/mL
OintmentTopical500 MCG/G
Cream
LotionTopical.05 g/100mL
LotionTopical0.05 mL/100mL
ShampooTopical0.05 g/100mL
SprayTopical0.5 mg/1mL
ShampooTopical500 Mikrogramm/g
ShampooTopical0.05 %
ShampooTopical0.05 mL/100mL
SprayTopical0.05 % w/w
SolutionCutaneous0.05 % w/w
LotionCutaneous0.050 g
SolutionCutaneous0.050 g
OintmentTopical0.05 g
ShampooTopical0.5 mg/1mL
KitTopical0.5 mg/1mL
OintmentTopical0.05 % w/w
SolutionTopical0.05 %w/v
ShampooTopical
CreamTopical0.05 %w/w
CreamTopical0.05 g/100g
SolutionTopical0.4625 mg/1mL
SolutionTopical0.5 mg/1g
LotionTopical50 mg
Cream0.5 mg/g
CreamTopical0.5 mg/g
SolutionTopical0.5 mg/g
CreamTopical25 gr
CreamTopical50 gr
OintmentTopical25 gr
OintmentTopical50 gr
LotionTopical0.05 %
SolutionTopical.05 %
LotionTopical0.05 % w/w
CreamTopical0.05 g
Cream0.05 % w/w
GelTopical
ShampooTopical500 MCG/G
OintmentTopical
LotionTopical0.15 mg/1g
CreamTopical0.25 mg/1g
CreamIntravenous0.05 %
OintmentIntravenous0.05 %
SolutionTopical
CreamTopical
GelTopical0.05 g
Ointment
OintmentTopical.05 %
Aerosol, foamTopical0.05 %
Aerosol, foamTopical0.05 % w/w
EmulsionTopical500 MCG/G
CreamCutaneous0.0500 g
CreamTopical0.05 %
OintmentTopical0.05 %
LotionTopical25 ml
OintmentCutaneous
CreamTopical0.05 % w/w
ShampooTopical0.05 % w/w
SolutionTopical0.05 %
KitTopical0.5 mg/1g
CapsuleOral0.050 g
CreamCutaneous0.050 g
Aerosol, foam; kitTopical0.5 mg/1g
SolutionTopical0.05 g
Ointment0.05 %w/w
Cream0.05 %w/w
Lotion0.05 %w/w
OintmentTopical0.05 %w/w
Prices
Unit descriptionCostUnit
Clobex 0.05% Lotion 118ml Bottle513.56USD bottle
Clobex Spray 0.05% Liquid 125ml Bottle501.7USD bottle
Olux 0.05% Foam 100 gm Can443.77USD can
Olux-E 0.05% Foam 100 gm Can384.32USD can
Olux Olux-E Complete Pack 0.05 & 0.05% Miscellaneous 110 gm Can373.65USD can
Clobex 0.05% Shampoo 118ml Bottle365.67USD bottle
Clobetasol Propionate 0.05% Foam 100 gm Can326.37USD can
Clobex 0.05% Lotion 59ml Bottle280.8USD bottle
Clobex Spray 0.05% Liquid 59ml Bottle278.93USD bottle
Olux 0.05% Foam 50 gm Can239.07USD can
Temovate 0.05% Cream 60 gm Tube234.19USD tube
Temovate 0.05% Gel 60 gm Tube234.19USD tube
Temovate E 0.05% Cream 60 gm Tube234.19USD tube
Clobetasol Propionate 0.05% Foam 50 gm Can177.05USD can
Temovate 0.05% Ointment 30 gm Tube132.55USD tube
Temovate 0.05% Solution 50ml Bottle113.82USD bottle
Temovate 0.05% Cream 45 gm Tube95.43USD tube
Clobetasol Propionate 0.05% Gel 60 gm Tube93.82USD tube
Temovate 0.05% Ointment 15 gm Tube82.1USD tube
Clobetasol 17-prop powder70.74USD g
Clobetasol Propionate 0.05% Cream 60 gm Tube64.15USD tube
Clobetasol Propionate 0.05% Ointment 60 gm Tube64.15USD tube
Clobetasol Propionate 0.05% Gel 30 gm Tube51.66USD tube
Clobetasol Propionate 0.05% Ointment 45 gm Tube50.56USD tube
Clobetasol Propionate 0.05% Cream 45 gm Tube48.57USD tube
Temovate 0.05% Gel 15 gm Tube47.38USD tube
Temovate E 0.05% Cream 15 gm Tube44.9USD tube
Clobetasol Propionate 0.05% Solution 50ml Bottle41.18USD bottle
Clobetasol Propionate 0.05% Cream 30 gm Tube34.79USD tube
Clobetasol Propionate 0.05% Ointment 30 gm Tube34.79USD tube
Clobetasol Propionate 0.05% Gel 15 gm Tube28.86USD tube
Clobetasol Propionate 0.05% Solution 25ml Bottle26.99USD bottle
Clobetasol Propionate 0.05% Cream 15 gm Tube24.94USD tube
Clobetasol Propionate 0.05% Ointment 15 gm Tube24.1USD tube
Olux 0.05% foam6.77USD g
Olux-e 0.05% foam5.9USD g
Clobex 0.05% topical lotion4.58USD ml
Temovate emollient 0.05% crm3.75USD g
Olux-olux-e complete pack3.43USD g
Temovate 0.05% cream3.29USD g
Cormax 0.05% cream2.06USD g
Embeline 0.05% cream1.86USD g
Clobetasol 0.05% cream1.43USD g
Dermovate 0.05 % Cream0.72USD g
Dermovate 0.05 % Ointment0.72USD g
Dermovate 0.05 % Lotion0.63USD g
Mylan-Clobetasol 0.05 % Cream0.38USD g
Mylan-Clobetasol 0.05 % Ointment0.38USD g
Novo-Clobetasol 0.05 % Cream0.38USD g
Novo-Clobetasol 0.05 % Ointment0.38USD g
Pms-Clobetasol 0.05 % Cream0.38USD g
Pms-Clobetasol 0.05 % Ointment0.38USD g
Ratio-Clobetasol 0.05 % Cream0.38USD g
Ratio-Clobetasol 0.05 % Ointment0.38USD g
Taro-Clobetasol 0.05 % Cream0.38USD g
Taro-Clobetasol 0.05 % Ointment0.38USD g
Mylan-Clobetasol 0.05 % Lotion0.33USD g
Pms-Clobetasol 0.05 % Lotion0.33USD g
Ratio-Clobetasol 0.05 % Lotion0.33USD g
Taro-Clobetasol 0.05 % Lotion0.33USD g
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2333869No2009-01-062019-09-08Canada flag
CA2333427No2007-01-092019-06-17Canada flag
US6126920No2000-10-032016-03-01US flag
US8460641No2013-06-112028-11-05US flag
US8962000No2015-02-242025-08-31US flag
US6730288No2004-05-042019-09-08US flag
US7029659No2006-04-182019-09-08US flag
US6106848No2000-08-222017-09-22US flag
US7700081No2010-04-202022-01-03US flag
US8066975No2011-11-292019-06-17US flag
US7316810No2008-01-082019-06-17US flag
US8066976No2011-11-292019-06-17US flag
US5990100No1999-11-232018-03-24US flag
US5972920No1999-10-262018-02-12US flag
US9855334No2018-01-022035-03-11US flag
US9956231No2018-05-012030-08-31US flag
US10064875No2018-09-042030-08-31US flag
US10588914No2020-03-172030-08-31US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)196Health Canada Label
logP3.50SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.00413 mg/mLALOGPS
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 Area80.67 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity119.32 m3·mol-1Chemaxon
Polarizability48.27 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9814
Caco-2 permeable+0.812
P-glycoprotein substrateSubstrate0.7852
P-glycoprotein inhibitor INon-inhibitor0.7375
P-glycoprotein inhibitor IINon-inhibitor0.7683
Renal organic cation transporterNon-inhibitor0.7883
CYP450 2C9 substrateNon-substrate0.8533
CYP450 2D6 substrateNon-substrate0.9077
CYP450 3A4 substrateSubstrate0.7967
CYP450 1A2 substrateNon-inhibitor0.9412
CYP450 2C9 inhibitorNon-inhibitor0.8713
CYP450 2D6 inhibitorNon-inhibitor0.8327
CYP450 2C19 inhibitorNon-inhibitor0.9126
CYP450 3A4 inhibitorNon-inhibitor0.5411
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9129
Ames testNon AMES toxic0.8848
CarcinogenicityNon-carcinogens0.935
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.1435 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9314
hERG inhibition (predictor II)Non-inhibitor0.5569
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-05fr-1920000000-defac8a82087405b74df
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a6r-0596000000-b19d97ac39952d18b68e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03mj-3971000000-8f42562c23aaf5e5d240
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0009400000-39c8cb579009148b9cee
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-9001600000-a135893581ff8107e2ff
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066r-0138900000-ec7a81b8427148cb8950
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9002000000-5cefecb1bb52448e3eff
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-9002100000-86119a7e2781201b6ca6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05u6-1957100000-5e97a76acec5362b3849
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-201.02147
predicted
DeepCCS 1.0 (2019)
[M+H]+202.91689
predicted
DeepCCS 1.0 (2019)
[M+Na]+209.86478
predicted
DeepCCS 1.0 (2019)

Targets

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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. 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. [Article]
  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. [Article]
  3. Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Structural molecule activity
Specific Function
Plays important roles in the innate immune response as effector of glucocorticoid-mediated responses and regulator of the inflammatory process. Has anti-inflammatory activity (PubMed:8425544). Play...
Gene Name
ANXA1
Uniprot ID
P04083
Uniprot Name
Annexin A1
Molecular Weight
38713.855 Da
References
  1. Serres M, Viac J, Comera C, Schmitt D: Expression of annexin I in freshly isolated human epidermal cells and in cultured keratinocytes. Arch Dermatol Res. 1994;286(5):268-72. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. FDA Approved Drug Products: Olux-E Clobetasol Propionate Topical Aerosol Foam [Link]
  2. FDA Approved Drug Products: Olux Clobetasol Propionate Topical Aerosol Foam [Link]
  3. FDA Approved Drug Products: Clobex Clobetasol Propionate Topical Lotion [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
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. Ahmad N, Mukhtar H: Cytochrome p450: a target for drug development for skin diseases. J Invest Dermatol. 2004 Sep;123(3):417-25. doi: 10.1111/j.0022-202X.2004.23307.x. [Article]
  2. Usui T, Saitoh Y, Komada F: Induction of CYP3As in HepG2 cells by several drugs. Association between induction of CYP3A4 and expression of glucocorticoid receptor. Biol Pharm Bull. 2003 Apr;26(4):510-7. doi: 10.1248/bpb.26.510. [Article]
  3. Pichard L, Fabre I, Daujat M, Domergue J, Joyeux H, Maurel P: Effect of corticosteroids on the expression of cytochromes P450 and on cyclosporin A oxidase activity in primary cultures of human hepatocytes. Mol Pharmacol. 1992 Jun;41(6):1047-55. [Article]
  4. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [Article]
  5. Olux monograph [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [Article]
  2. Smith G, Ibbotson SH, Comrie MM, Dawe RS, Bryden A, Ferguson J, Wolf CR: Regulation of cutaneous drug-metabolizing enzymes and cytoprotective gene expression by topical drugs in human skin in vivo. Br J Dermatol. 2006 Aug;155(2):275-81. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
References
  1. Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [Article]
  2. Schimmer B, Funder J (2018). 46. In Goodman & Gilman's: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [ISBN:978-1-25-958473-2]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [Article]
  2. Schimmer B, Funder J (2018). 46. In Goodman & Gilman's: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [ISBN:978-1-25-958473-2]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48