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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26ClFO4
Molecular Weight 408.891
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOBETASONE

SMILES

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

InChI

InChIKey=XXIFVOHLGBURIG-OZCCCYNHSA-N
InChI=1S/C22H26ClFO4/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/h6-7,9,12,15-16,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19-,20-,21-,22-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12775314 and http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con239418.pdf

Clobetasone is a corticosteroid used in dermatology, for treating such skin inflammation as seen in eczema, psoriasis and other forms of dermatitis, and ophthalmology. Topical clobetasone butyrate has shown minimal suppression of the Hypothalamic-pituitary-adrenal axis. It is available as clobetasone butyrate under the brand names Eumosone or Eumovate both manufactured by GlaxoSmithKline. Trimovate also contains Oxytetracycline, an antibiotic, and nystatin, an antifungal. Clobetasone butyrate is classed as a moderately potent topical corticosteroid. Clobetasone butyrate relieves the symptoms of a flare-up by reducing inflammation, itching and redness. It is not a cure for the condition, but it will help to relieve the symptoms. Although less potent topical steriods are often preferred for use in children, a short course of clobetasone butyrate may be prescribed for a child with severe eczema on the arms or legs. Short courses of clobetasone butyrate may also be prescribed for the treatment of psoriasis for areas such as the face, or the inside of elbows and behind the knees. In ophthalmology, clobetasone butyrate 0.1% eye drops have been shown to be safe and effective in the treatment of dry eyes in Sjögren's Syndrome.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.19 nM [EC50]
6080.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
EUMOVATE CREAM

Approved Use

Eumovate Cream is a moderately potent topical corticosteroid indicated for adults, elderly, children and infants for the relief of the inflammatory and pruritic manifestations of steroid responsive dermatoses. These include the following: - Atopic dermatitis - Irritant or allergic contact dermatitis - Seborrhoeic dermatitis - Photodermatitis - Otitis externa - Prurigo nodularis - Insect bite reactions

Launch Date

1976
Palliative
EUMOVATE CREAM

Approved Use

EUMOVATE is used to treat eczema and dermatitis

Launch Date

1976
Palliative
EUMOVATE CREAM

Approved Use

EUMOVATE is suitable for treating atopic eczema, photodermatitis, otitis externa, primary irritant and allergic dermatitis, prurigo nodularis, seborrhoeic dermatitis, and other steroid responsive skin conditions which do not require the use of a more active topical corticosteroid in children and adults.

Launch Date

1976
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Serum leptin level in children with atopic dermatitis-treated topical steroids.
2004 Jun
Highly potent and moderately potent topical steroids are effective in treating phimosis: a prospective randomized study.
2005 Apr
Use of nonprescription topical steroids: patients' experiences.
2005 Jun
Acrokeratoelastoidosis.
2005 May
Nocardia keratitis: a case report.
2006 Jan-Feb
Comparison of the effects of vitamin D products in a psoriasis plaque test and a murine psoriasis xenograft model.
2009 Dec 17
Patents

Sample Use Guides

Eumovate (clobetasone butyrate 0.05%) should be applied thinly and evenly to the affected area(s) of skin up to 2 times a day
Route of Administration: Topical
In Vitro Use Guide
Clobetasone butyrate depressed proliferation of cell strains derived from normal human foreskin at 10 ug/ml
Name Type Language
CLOBETASONE
INN   MI   WHO-DD  
INN  
Official Name English
21-CHLORO-9-FLUORO-17-HYDROXY-16.BETA.-METHYLPREGNA-1,4-DIENE-3,11,20-TRIONE
Systematic Name English
Clobetasone [WHO-DD]
Common Name English
CLOBETASONE BUTYRATE IMPURITY A [EP IMPURITY]
Common Name English
clobetasone [INN]
Common Name English
PREGNA-1,4-DIENE-3,11,20-TRIONE, 21-CHLORO-9-FLUORO-16-METHYL-17-HYDROXY-, (16.BETA.)-
Systematic Name English
CLOBETASONE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QS01CA11
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
WHO-VATC QD07AB01
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
WHO-ATC S01CA11
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
WHO-VATC QS01BA09
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
WHO-ATC S01BA09
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
WHO-ATC D07AB01
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
NCI_THESAURUS C521
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
Code System Code Type Description
WIKIPEDIA
CLOBETASONE
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
ECHA (EC/EINECS)
258-953-5
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
EVMPD
SUB06679MIG
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
RXCUI
108074
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL2308885
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
NCI_THESAURUS
C77408
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
INN
3155
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
PUBCHEM
71387
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID601023875
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
CAS
54063-32-0
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PRIMARY
MERCK INDEX
m3629
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY Merck Index
SMS_ID
100000084302
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
DRUG BANK
DB13158
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY
FDA UNII
LT69WY1J6D
Created by admin on Fri Dec 15 16:04:02 GMT 2023 , Edited by admin on Fri Dec 15 16:04:02 GMT 2023
PRIMARY