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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29FO4
Molecular Weight 376.4625
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESOXIMETASONE

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([H])C(=O)CO)O)F

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

Molecular Formula C22H29FO4
Molecular Weight 376.4625
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68003899 | http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204141s000lbl.pdf

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

Curator's Comment:: Kieslich, K., Kerb, U. and Raspe, G.; US. Patent 3,232,839; February 1,1966; assigned to Schering AG, Germany.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.5 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TOPICORT

Approved Use

Topicort® (desoximetasone cream USP) 0.05%, Topicort® (desoximetasone cream USP) 0.25%, and Topicort® (desoximetasone gel USP) 0.05% are indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Launch Date

2.25935999E11
Primary
TOPICORT

Approved Use

Topicort® Topical Spray is a corticosteroid indicated for the treatment of plaque psoriasis in patients 18 years of age or older.

Launch Date

1.36555201E12
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
16272 pg × h/mL
0.25 % 2 times / day steady-state, topical
dose: 0.25 %
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
DESOXIMETASONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
PubMed

PubMed

TitleDatePubMed
Compatibility of desoximetasone and tacrolimus.
2003 Dec
Quantitative determination of dexamethasone in bovine milk by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry.
2004 Jun 5
[Psoriasis and mud bath therapy: clinical-experimental study].
2005 Jul-Aug
Desoximetasone 0.25% and tacrolimus 0.1% ointments versus tacrolimus alone in the treatment of atopic dermatitis.
2006 Nov
Etanercept responsive acrodermatitis continua of Hallopeau: is a pattern developing?
2006 Oct
Cross-reactions to desoximetasone and mometasone furoate in a patient with multiple topical corticosteroid allergies.
2006 Sep
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

Apply a thin film of desoximetasone (Topicort®) to the affected skin areas twice daily. Rub in gently.
Route of Administration: Topical
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:02:16 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:16 UTC 2021
Record UNII
4E07GXB7AU
Record Status Validated (UNII)
Record Version
  • Download
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
NSC-759189
Code English
DESOXIMETASONE [MI]
Common Name English
DESOXIMETASONE [USP MONOGRAPH]
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 Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
NDF-RT N0000175450
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
WHO-VATC QD07AC03
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
NCI_THESAURUS C521
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
NDF-RT N0000175576
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
WHO-ATC D07XC02
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
WHO-ATC D07AC03
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
Code System Code Type Description
IUPHAR
7067
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
EVMPD
SUB07006MIG
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-845-3
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
FDA UNII
4E07GXB7AU
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
WIKIPEDIA
DESOXIMETASONE
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
EPA CompTox
382-67-2
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
CAS
382-67-2
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
NCI_THESAURUS
C47477
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
PUBCHEM
5311067
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
MESH
D003899
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
USP_CATALOG
1173508
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY USP-RS
INN
2467
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL1766
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
DRUG CENTRAL
819
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
DRUG BANK
DB00547
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
MERCK INDEX
M4201
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY Merck Index
RXCUI
3255
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY RxNorm
LACTMED
Desoximetasone
Created by admin on Fri Jun 25 21:02:16 UTC 2021 , Edited by admin on Fri Jun 25 21:02:16 UTC 2021
PRIMARY
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