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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28ClFO4
Molecular Weight 410.9075
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOBETASOL

SMILES

C[C@@]1([H])C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@]3([C@]([H])(C[C@]2(C)[C@]1(C(=O)CCl)O)O)F

InChI

InChIKey=FCSHDIVRCWTZOX-DVTGEIKXSA-N
InChI=1S/C22H28ClFO4/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/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H28ClFO4
Molecular Weight 410.9075
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:43:04 UTC 2021
Edited
by admin
on Sat Jun 26 13:43:04 UTC 2021
Record UNII
ADN79D536H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOBETASOL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CLOBETASOL [VANDF]
Common Name English
BETAMETHASONE VALERATE IMPURITY B [EP]
Common Name English
CLOBETASOL PROPIONATE IMPURITY G [EP]
Common Name English
BETAMETHASONE IMPURITY B [EP]
Common Name English
CLOBETASOL [MI]
Common Name English
CLOBETASOL [WHO-DD]
Common Name English
DOVATE
Brand Name English
21-CHLORO-9-FLUORO-11.BETA.,17-DIHYDROXY-16.BETA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Systematic Name English
CLOBECORT AMEX
Brand Name English
(11.BETA.,16.BETA.)-21-CHLORO-9-FLUORO-11,17-DIHYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Systematic Name English
PREGNA-1,4-DIENE-3,20-DIONE, 21-CHLORO-9-FLUORO-11,17-DIHYDROXY-16-METHYL-, (11.BETA.,16.BETA.)-
Systematic Name English
CLOBETASOL [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QD07CD01
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
NDF-RT N0000175450
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
WHO-ATC D07AD01
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
NDF-RT N0000175576
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
WHO-VATC QD07AD01
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
WHO-ATC D07CD01
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
NCI_THESAURUS C521
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
Code System Code Type Description
PUBCHEM
5311051
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
FDA UNII
ADN79D536H
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
ChEMBL
CHEMBL1159650
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
CAS
25122-41-2
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
LACTMED
Clobetasol
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
ECHA (EC/EINECS)
246-633-8
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
NCI_THESAURUS
C65339
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
MERCK INDEX
M3628
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY Merck Index
INN
3154
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
MESH
D002990
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
HSDB
7994
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
DRUG BANK
DB11750
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
EPA CompTox
25122-41-2
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
RXCUI
2590
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY RxNorm
EVMPD
SUB06678MIG
Created by admin on Sat Jun 26 13:43:05 UTC 2021 , Edited by admin on Sat Jun 26 13:43:05 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY