U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H32ClFO5
Molecular Weight 466.97
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOBETASOL PROPIONATE

SMILES

[H][C@@]12C[C@H](C)[C@](OC(=O)CC)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

InChI

InChIKey=CBGUOGMQLZIXBE-XGQKBEPLSA-N
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

HIDE SMILES / InChI
CLOBETASOL, a derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in the treatment of psoriasis but may cause marked adrenocortical suppression. For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp. 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. Topical corticosteroids share anti-inflammatory, antipruritic, and vasoconstrictive properties. The mechanism of the anti-inflammatory activity of topical steroids is unclear. 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, enters the cell nucleus and modifies genetic transcription (transrepression/transactivation).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
OLUX E

Approved Use

Olux-E Foam is indicated for the treatment of inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients 12 years of age or older. Treatment should be limited to 2 consecutive weeks and patients should not use greater than 50 grams per week. Patients should be instructed to use Olux-E Foam for the minimum amount of time necessary to achieve the desired results. Use in pediatric patients under 12 years of age is not recommended because of numerically high rates of hypothalamic-pituitary-adrenal (HPA) axis suppression seen in patients under 12 years of age

Launch Date

1.16847359E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
59 pg/mL
3.57 g 2 times / day multiple, topical
dose: 3.57 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
CLOBETASOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
562 pg × h/mL
3.57 g 2 times / day multiple, topical
dose: 3.57 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
CLOBETASOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18 h
12.5 mg single, topical
dose: 12.5 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
CLOBETASOL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2.5%
CLOBETASOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.05 % 2 times / day multiple, topical
Recommended
Dose: 0.05 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.05 %, 2 times / day
Sources: Page: p.420
unhealthy, 36
n = 25
Health Status: unhealthy
Condition: Psoriasis
Age Group: 36
Sex: M+F
Population Size: 25
Sources: Page: p.420
Disc. AE: Pruritus...
AEs leading to
discontinuation/dose reduction:
Pruritus (4%)
Sources: Page: p.420
AEs

AEs

AESignificanceDosePopulation
Pruritus 4%
Disc. AE
0.05 % 2 times / day multiple, topical
Recommended
Dose: 0.05 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.05 %, 2 times / day
Sources: Page: p.420
unhealthy, 36
n = 25
Health Status: unhealthy
Condition: Psoriasis
Age Group: 36
Sex: M+F
Population Size: 25
Sources: Page: p.420
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Tox targets
PubMed

PubMed

TitleDatePubMed
Clobetasol down-regulates SLPI expression in U937 monocytoid cells.
2012 Feb
Clobetasol synergistically diminishes Ciz1 expression with genistein in U937 cells.
2012 Feb
Patents

Sample Use Guides

Apply a thin layer of Olux-E Foam (clobetasol propionate) to the affected area(s) twice daily, morning and evening.
Route of Administration: Topical
Clobetasol treatment of U937 cells induced an up- and down-regulation of secretory leukocyte peptidase inhibitor (SLPI) expression in a dose-dependent manner.
Name Type Language
CLOBETASOL PROPIONATE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
CLOBETASOL 17-PROPIONATE
MI  
Common Name English
CCI 4725
Code English
GR-2/925
Code English
CLOBETASOL PROPIONATE [USP-RS]
Common Name English
CLOBETASOL PROPIONATE [MART.]
Common Name English
21-Chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-propionate
Systematic Name English
CLOBETASOL PROPIONATE [ORANGE BOOK]
Common Name English
OLUX
Brand Name English
IMPEKLO
Brand Name English
CLOBETASOL PROPIONATE [MI]
Common Name English
TEMOVATE
Brand Name English
PREGNA-1,4-DIENE-3,20-DIONE, 21-CHLORO-9-FLUORO-11-HYDROXY-16-METHYL-17-(1-OXOPROPOXY)-, (11.BETA.,16.BETA.)-
Systematic Name English
CLOBETASOL PROPIONATE [USAN]
Common Name English
CLOBETASOL PROPIONATE [USP IMPURITY]
Common Name English
GR 2/925
Code English
CLOBETASOL PROPIONATE [JAN]
Common Name English
CCI-4725
Code English
Clobetasol propionate [WHO-DD]
Common Name English
DERMOVATE
Brand Name English
CLOBETASOL PROPIONATE [VANDF]
Common Name English
IMPOYZ
Brand Name English
CLOBETASOL PROPIONATE [USP MONOGRAPH]
Common Name English
CLOBETASOL 17-PROPIONATE [MI]
Common Name English
NSC-758634
Code English
CORMAX
Brand Name English
EMBELINE
Brand Name English
CLOBEX
Brand Name English
PSOREX
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
Code System Code Type Description
USAN
U-34
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
DRUG CENTRAL
4452
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID6045907
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
ECHA (EC/EINECS)
246-634-3
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
IUPHAR
7062
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
WIKIPEDIA
CLOBETASOL PROPIONATE
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
MERCK INDEX
m3628
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY Merck Index
DAILYMED
779619577M
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL1159650
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
RXCUI
21245
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY RxNorm
CAS
25122-46-7
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
NSC
758634
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
EVMPD
SUB01346MIG
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
PUBCHEM
32798
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
RS_ITEM_NUM
1138405
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
SMS_ID
100000091516
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
FDA UNII
779619577M
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
NCI_THESAURUS
C28934
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
DRUG BANK
DB01013
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY
CHEBI
31414
Created by admin on Fri Dec 15 15:19:46 UTC 2023 , Edited by admin on Fri Dec 15 15:19:46 UTC 2023
PRIMARY