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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29FO4
Molecular Weight 376.4617
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESOXIMETASONE

SMILES

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

InChI

InChIKey=VWVSBHGCDBMOOT-IIEHVVJPSA-N
InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1

HIDE SMILES / InChI

Description

Desoximetasone (Topicort®) is a topical anti-inflammatory glucocorticoid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses and for the treatment of plaque psoriasis in patients 18 years of age or older. The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. They play a role in cellular signaling, immune function, inflammation and protein regulation; however, the precise mechanism of action in psoriasis is unknown. The mechanism of anti-inflammatory activity of the topical corticosteroids is also unclear. Various laboratory methods, including vasoconstrictor assays, are used to compare and predict potencies and/or clinical efficacies of the topical corticosteroids. There is some evidence to suggest that a recognizable correlation exists between vasoconstrictor potency and therapeutic efficacy in man.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.5 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TOPICORT
Primary
TOPICORT
PubMed

PubMed

TitleDatePubMed
Desoximetasone 0.25% and tacrolimus 0.1% ointments versus tacrolimus alone in the treatment of atopic dermatitis.
2006 Nov
Iatrogenic hyperadrenocorticism and steatohepatitis caused by unapproved medicine.
2008
Activity of different desoximetasone preparations compared to other topical corticosteroids in the vasoconstriction assay.
2008
Comparison of tissue viability imaging and colorimetry: skin blanching.
2009 Feb
Emotional lability secondary to the application of a very potent topical corticosteroid.
2009 Jul-Sep
Compatibility of tacrolimus ointment with corticosteroid ointments of varying potencies.
2009 May-Jun
Management of alopecia areata.
2010 Jul 23
Update on the management of chronic eczema: new approaches and emerging treatment options.
2010 Jul 28
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

In Vivo Use Guide
Apply a thin film of desoximetasone (Topicort®) to the affected skin areas twice daily. Rub in gently.
Route of Administration: Topical
In Vitro Use Guide
Dexamethasone (DEX) (10^-6 M) downregulated human glucocorticoid receptor alpha (hGRalpha) mRNA at 6 and 24 h (55 +/- 8 and 58 +/- 5% of control, respectively; P < 0.01), whereas it decreased human glucocorticoid receptor beta (hGRbeta) mRNA only at 6 h (55 +/- 7% of control; P < 0.01). Downregulation of hGRalpha and hGRbeta mRNAs occurred even in the presence of cycloheximide. Actinomycin-D studies revealed that DEX enhanced the stabilization of hGRalpha and hGRbeta messages.
Name Type Language
DESOXIMETASONE
INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
DESOXYMETHASONE
Common Name English
DEXAMETHASONE SPECIFIED IMPURITY F [EP]
Common Name English
A-41-304
Code English
DESOXIMETASONE [WHO-DD]
Common Name English
DESOXIMETASONE [USP-RS]
Common Name English
R 2113
Code English
R-2113
Code English
DESOXIMETASONE [VANDF]
Common Name English
TOPICORT
Brand Name English
HOE-304
Code English
J83.644C
Code English
DESOXIMETASONE [ORANGE BOOK]
Common Name English
DESOXIMETASONE [MART.]
Common Name English
A-41304
Code English
9-FLUORO-11B,21-DIHYDROXY-16A-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Systematic Name English
DESOXIMETASONE [MI]
Common Name English
DESOXIMETASONE [USAN]
Common Name English
DESOXIMETASONE [USP]
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11,21-DIHYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.)-
Systematic Name English
DESOXIMETASONE [JAN]
Common Name English
DEXAMETHASONE IMPURITY F [EP]
Common Name English
DESOXIMETASONE [INN]
Common Name English
9-FLUORO-11.BETA.,21-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Systematic Name English
HOE 304
Code English
Classification Tree Code System Code
WHO-VATC QD07XC02
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
NDF-RT N0000175450
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
WHO-VATC QD07AC03
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
NDF-RT N0000175576
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
WHO-ATC D07XC02
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
WHO-ATC D07AC03
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
Code System Code Type Description
IUPHAR
7067
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
EVMPD
SUB07006MIG
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
ECHA (EC/EINECS)
206-845-3
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
WIKIPEDIA
DESOXIMETASONE
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
EPA CompTox
382-67-2
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
CAS
382-67-2
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
NCI_THESAURUS
C47477
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
PUBCHEM
5311067
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY SWITZERF
MESH
D003899
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
LactMed
382-67-2
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
INN
2467
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
ChEMBL
CHEMBL1766
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
DRUG BANK
DB00547
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY
MERCK INDEX
M4201
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY Merck Index
RXCUI
3255
Created by admin on Tue Mar 06 11:23:21 UTC 2018 , Edited by admin on Tue Mar 06 11:23:21 UTC 2018
PRIMARY RxNorm