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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Primary TargetPharmacologyConditionPotency
5.5 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TOPICORT
Primary
TOPICORT

AUC

ValueDoseCo-administeredAnalytePopulation
16272 pg × h/mL
0.25 % 2 times / day steady-state, topical
DESOXIMETASONE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

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
Record UNII
4E07GXB7AU
Record Status Validated (UNII)
Record Version