DESOXIMETASONE

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 Search

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

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/073210Orig1s029Lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 173 Target ID: CHEMBL2034 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/073210Orig1s029Lbl.pdf	Agonist 2752		5.5 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatoses 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/073210Orig1s029Lbl.pdf	Primary		Approved 8583	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
Plaque psoriasis 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204141s000lbl.pdf	Primary		Approved 8583	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

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204141Orig1s000PharmR.pdf Page: 14.0	likely

Sourcing

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

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Update on the management of chronic eczema: new approaches and emerging treatment options.	2010-07-28	21437065
Management of alopecia areata.	2010-07-23	20656774
Emotional lability secondary to the application of a very potent topical corticosteroid.	2009-11-03	19881052
Compatibility of tacrolimus ointment with corticosteroid ointments of varying potencies.	2009-05-12	19426622
Comparison of tissue viability imaging and colorimetry: skin blanching.	2009-02	19152574
Iatrogenic hyperadrenocorticism and steatohepatitis caused by unapproved medicine.	2008	18591846
Activity of different desoximetasone preparations compared to other topical corticosteroids in the vasoconstriction assay.	2008	18523415
Desoximetasone 0.25% and tacrolimus 0.1% ointments versus tacrolimus alone in the treatment of atopic dermatitis.	2006-11	17186796
Etanercept responsive acrodermatitis continua of Hallopeau: is a pattern developing?	2006-10	17039659
Cross-reactions to desoximetasone and mometasone furoate in a patient with multiple topical corticosteroid allergies.	2006-09	16956468
[Psoriasis and mud bath therapy: clinical-experimental study].	2005-12-14	16342515
Quantitative determination of dexamethasone in bovine milk by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry.	2004-06-05	15113540
Compatibility of desoximetasone and tacrolimus.	2003-12	14711143

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:38 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:38 GMT 2025`
Record UNII	4E07GXB7AU
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DESOXIMETASONE

Official Name

English

TOPICORT

Preferred 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

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-11?,21-dihydroxy-16?-methylpregna-1,4-diene-3,20-dione

Systematic Name

English

HOE 304

Code

English

Classification Tree Code System Code

WHO-VATC

QD07XC02