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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

1977
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

2013
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
Quantitative determination of dexamethasone in bovine milk by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry.
2004 Jun 5
Iatrogenic hyperadrenocorticism and steatohepatitis caused by unapproved medicine.
2008
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:11 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
NDF-RT N0000175450
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
WHO-VATC QD07AC03
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
WHO-ATC D07XC02
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
WHO-ATC D07AC03
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
Code System Code Type Description
IUPHAR
7067
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
EVMPD
SUB07006MIG
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-845-3
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
FDA UNII
4E07GXB7AU
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
WIKIPEDIA
DESOXIMETASONE
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID3045647
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
CAS
382-67-2
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
NCI_THESAURUS
C47477
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
NSC
759189
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
PUBCHEM
5311067
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
MESH
D003899
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
DAILYMED
4E07GXB7AU
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
CHEBI
691037
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
SMS_ID
100000083193
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
INN
2467
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL1766
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
DRUG CENTRAL
819
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
RS_ITEM_NUM
1173508
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY
DRUG BANK
DB00547
Created by admin on Fri Dec 15 15:08:11 GMT 2023 , Edited by admin on Fri Dec 15 15:08:11 GMT 2023
PRIMARY
MERCK INDEX
m4201
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY Merck Index
RXCUI
3255
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 2023
PRIMARY RxNorm
LACTMED
Desoximetasone
Created by admin on Fri Dec 15 15:08:12 GMT 2023 , Edited by admin on Fri Dec 15 15:08:12 GMT 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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