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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

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

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 376.4617
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

Schering
47
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

1977
44
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 5.5 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Approved
8429
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204141s004lbl.pdf
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
CYP
270
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 likely
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:691037
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:691037
ChemicalBook
CB0346960
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0346960
MolPort
MolPort-003-941-111
https://www.molport.com/shop/molecule-link/MolPort-003-941-111
ZINC
ZINC000004212854
http://zinc15.docking.org/substances/ZINC000004212854
eMolecules
36554167
https://www.emolecules.com/cgi-bin/more?vid=36554167
PubMed

PubMed

TitleDatePubMed
Compatibility of desoximetasone and tacrolimus.
2003 Dec
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
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
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

Patents

20020002155
1
20020012680
32
JP2007513165A
55
JP2012500104A
107
US3099654
1
US3232839
1
US5990100
1
US8277780
1
US8715624
1

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:11 UTC 2023
Edited
by admin
on Fri Dec 15 15:08:11 UTC 2023
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
A-41-304
Code 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
Desoximetasone [WHO-DD]
Common Name English
NSC-759189
Code English
DESOXIMETASONE [MI]
Common Name English
DESOXIMETASONE [USP MONOGRAPH]
Common Name English
DESOXIMETASONE [USAN]
Common Name English
DESOXIMETASONE [USP IMPURITY]
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 IMPURITY]
Common Name English
desoximetasone [INN]
Common Name English
9-Fluoro-11β,21-dihydroxy-16α-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 Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
NDF-RT N0000175450
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
WHO-VATC QD07AC03
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
WHO-ATC D07XC02
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
WHO-ATC D07AC03
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
Code System Code Type Description
IUPHAR
7067
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
EVMPD
SUB07006MIG
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-845-3
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
FDA UNII
4E07GXB7AU
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
WIKIPEDIA
DESOXIMETASONE
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID3045647
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
CAS
382-67-2
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
NCI_THESAURUS
C47477
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
NSC
759189
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
PUBCHEM
5311067
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
MESH
D003899
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
DAILYMED
4E07GXB7AU
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
CHEBI
691037
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
SMS_ID
100000083193
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
INN
2467
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL1766
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
DRUG CENTRAL
819
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
RS_ITEM_NUM
1173508
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
DRUG BANK
DB00547
Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023
PRIMARY
MERCK INDEX
m4201
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY Merck Index
RXCUI
3255
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY RxNorm
LACTMED
Desoximetasone
Created by admin on Fri Dec 15 15:08:12 UTC 2023 , Edited by admin on Fri Dec 15 15:08:12 UTC 2023
PRIMARY
Related Record Type Details
Structure of DEXAMETHASONE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of Desoximetasone Acid
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DEXAMETHASONE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 9-FLUORO-11.BETA.,21-DIHYDROXY-16.ALPHA.-METHYLPREGNA-4-ENE-3,20-DIONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 21-DEHYDRODESOXYMETASONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of DESOXIMETASONE
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