Flumethasone

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28F2O5
Molecular Weight	410.4515
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO

InChI

InChIKey=WXURHACBFYSXBI-GQKYHHCASA-N

InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H28F2O5
Molecular Weight	410.4515
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00663
Curator's Comment: Description was created based on several sources, including

Flumethasone or flumetasone is a corticosteroid and is an agonist of a glucocorticoid receptor with anti-inflammatory, antipruritic and vasoconstrictive properties. Flumethasone is often formulated as the pivalic acid ester, flumetasone pivalate. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Flumethasone binds to plasma transcortin, and it becomes active when it is not bound to transcortin. Flumethasone is used for the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin condition.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 173 Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00663	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Corticosteroid-responsive dermatoses 17 Sources: https://web.archive.org/web/20160728165659/http://drug.mynahcare.com:80/drugs/genericdetail/flumethasone-OTMw	Primary		Approved 8583	LOCORTEN Approved Use This medication is used in corticosteroid-responsive dermatoses.

C_max

Value	Dose	Co-administered	Analyte	Population
10 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30080272/	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		FLUMETHASONE serum	Equus caballus population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
5.32 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30080272/	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		FLUMETHASONE serum	Equus caballus population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30080272/	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		FLUMETHASONE serum	Equus caballus population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	11-beta-HSD1 33 11-beta-HSD2 48

Drug as victim

Target	Modality	Activity
11-beta-HSD1 33	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.3109/03602532.2013.853078	yes
11-beta-HSD2 48	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.3109/03602532.2013.853078	yes
CYP3A4 1946	substrate 4014 Sources: https://ncit-stage.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI_Thesaurus&version=21.01d&code=C65717&ns=ncit&type=relationship&key=1748712643&b=1&n=0&vse=null	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:34764	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34764
ChemicalBook	CB2324823	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2324823
eMolecules	29543007	https://www.emolecules.com/cgi-bin/more?vid=29543007
eMolecules	538529	https://www.emolecules.com/cgi-bin/more?vid=538529
MolPort	MolPort-003-847-393	https://www.molport.com/shop/molecule-link/MolPort-003-847-393
ZINC	ZINC000003983936	http://zinc15.docking.org/substances/ZINC000003983936

PubMed

Title	Date	PubMed
Screening and quantitative confirmatory method for the analysis of glucocorticoids in bovine milk using liquid chromatography-tandem mass spectrometry.	2010-12-15	21140678
Quantitative determination of corticosteroids in bovine milk using mixed-mode polymeric strong cation exchange solid-phase extraction and liquid chromatography-tandem mass spectrometry.	2010-12-01	20643526
Quantification of corticosteroids in bovine urine using selective solid phase extraction and reversed-phase liquid chromatography/tandem mass spectrometry.	2010-06-01	20457014
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.	2010-04	20155493
Simultaneous determination of corticosteroids, androgens, and progesterone in river water by liquid chromatography-tandem mass spectrometry.	2010-02	20071003
Pivotal Advance: Pharmacological manipulation of inflammation resolution during spontaneously resolving tissue neutrophilia in the zebrafish.	2010-02	19850882
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.	2009-11-13	19423120
Validation of a solid-phase extraction and ultra-performance liquid chromatographic tandem mass spectrometric method for the detection of 16 glucocorticoids in pig tissues.	2009-06-03	19485221
Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry.	2009-04-01	19286019
A simple and rapid ESI-LC-MS/MS method for simultaneous screening of doping agents in urine samples.	2009-04	20336223
Lecithin based nanoemulsions: A comparative study of the influence of non-ionic surfactants and the cationic phytosphingosine on physicochemical behaviour and skin permeation.	2009-03-31	19073240
A liquid chromatography method using a monolithic column for the determination of corticoids in animal feed and animal feeding water.	2008-08	18506427
Optimization of solid phase extraction clean up and validation of quantitative determination of corticosteroids in urine by liquid chromatography-tandem mass spectrometry.	2008-06-09	18486661
Flexor carpi ulnaris tendonopathy in a Weimaraner.	2007-10	17903127
Rapid multi-residue method for the quantitative determination and confirmation of glucocorticosteroids in bovine milk using liquid chromatography-electrospray ionization-tandem mass spectrometry.	2007-04-04	17386789
Effect of selected fluorinated drugs in a "ringing" gel on rheological behaviour and skin permeation.	2007-04	17055710
High throughput HPLC-ESI-MS method for the quantitation of dexamethasone in blood plasma.	2007-01-04	16887316
A chromatography method for the screening and confirmatory detection of dexamethasone.	2006-12	22063222
Medical treatment of vulvar squamous cell hyperplasia.	2006-12	17010347
G-protein-coupled glucocorticoid receptors on the pituitary cell membrane.	2005-08-01	16079279
Regression of subcorneal pustular dermatosis type of IgA pemphigus lesions with azithromycin.	2005-08	16038746
Effect of steroidal and non-steroidal anti-inflammatory drugs on inflammatory markers in calves with experimentally-induced bronchopneumonia.	2005-07-29	16048041
Detection of synthetic corticosteroids in bovine urine by chemiluminescence high-performance liquid chromatography.	2005-06-01	15924320
Confirmation of synthetic glucocorticoids with liquid chromatography/mass spectrometry: organization and results of an international interlaboratory comparison test.	2005-03-12	15759730
Otic drops used to clear a blocked grommet: an in vitro prospective randomized controlled study with blinded assessment.	2004-12	15533145
Transactivation via the human glucocorticoid and mineralocorticoid receptor by therapeutically used steroids in CV-1 cells: a comparison of their glucocorticoid and mineralocorticoid properties.	2004-09	15362971
Development of a dual luciferase reporter screening assay for the detection of synthetic glucocorticoids in animal tissues.	2003-12	14737223
Effect of steroidal and non-steroidal anti-inflammatory drugs in combination with long-acting oxytetracycline on non-specific immunity of calves suffering from enzootic bronchopneumonia.	2003-10-08	14516708
Immunochemical screening and liquid chromatographic-tandem mass spectrometric confirmation of drug residues in edible tissues of calves injected with a therapeutic dose of the synthetic glucocorticoids dexamethasone and flumethasone.	2003-01-01	12502428
A high-performance liquid chromatography/tandem mass spectrometric screening method for eight synthetic corticosteroids in bovine feces and the simultaneous differentiation between dexamethasone and betamethasone.	2002	12203252
Determination of flumethasone in calf urine and serum by liquid chromatography-tandem mass spectrometry.	2001-05-05	11393713
Accelerated solvent extraction and liquid chromatography-tandem mass spectrometry quantitation of corticosteroid residues in bovine liver.	2001-04-05	11334334

Patents

Sample Use Guides

In Vivo Use Guide

Apply a sparingly thin layer of 0.02% cream, ointment or lotion over affected areas bid-tid for 7-10 days.

Route of Administration: Topical

In Vitro Use Guide

Flumethasone inhibited PAF-induced N-PMN (neutrophils from newborn calves) aggregation at the highest dose - 122 uM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:33:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:33:05 GMT 2025`
Record UNII	LR3CD8SX89
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Flumethasone

Official Name

English

FLUMETASONE

Preferred Name

English

FLUMETHASONE [USAN]

Common Name

English

U-10,974

Code

English

NSC-54702

Code

English

6?,9-Difluoro-11?,17,21-trihydroxy-16?-methylpregna-1,4-diene-3,20-dione

Systematic Name

English

FLUMETHASONE [GREEN BOOK]

Common Name

English

FLUCORT

Brand Name

English

FLUMETHASONE [MI]

Common Name

English

U-10974

Code

English

flumetasone [INN]

Common Name

English

Flumetasone [WHO-DD]

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 6,9-DIFLUORO-11,17,21-TRIHYDROXY-16-METHYL-, (6.ALPHA.,11.BETA.,16.ALPHA.)-

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

D07BB01