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

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])C[C@H](F)C4=CC(=O)C=C[C@]34C

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 172 Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00663	Agonist 2678

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 8429	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 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	11-beta-HSD1 12 11-beta-HSD2 27

Drug as victim

Target	Modality	Activity
11-beta-HSD1 12	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.3109/03602532.2013.853078	yes
11-beta-HSD2 27	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.3109/03602532.2013.853078	yes
CYP3A4 1737	substrate 3367 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
MolPort	MolPort-003-847-393	https://www.molport.com/shop/molecule-link/MolPort-003-847-393
ZINC	ZINC000003983936	http://zinc15.docking.org/substances/ZINC000003983936
eMolecules	29543007	https://www.emolecules.com/cgi-bin/more?vid=29543007
eMolecules	538529	https://www.emolecules.com/cgi-bin/more?vid=538529

PubMed

Title	Date	PubMed
		252159923
Determination of flumethasone in calf urine and serum by liquid chromatography-tandem mass spectrometry.	2001 May 5	11393713
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
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 Jan 1	12502428
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 Oct 8	14516708
Otic drops used to clear a blocked grommet: an in vitro prospective randomized controlled study with blinded assessment.	2004 Dec	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 Sep	15362971
Regression of subcorneal pustular dermatosis type of IgA pemphigus lesions with azithromycin.	2005 Aug	16038746
Effect of steroidal and non-steroidal anti-inflammatory drugs on inflammatory markers in calves with experimentally-induced bronchopneumonia.	2005 Jul-Aug	16048041
A chromatography method for the screening and confirmatory detection of dexamethasone.	2006 Dec	22063222
Medical treatment of vulvar squamous cell hyperplasia.	2006 Dec	17010347
Rapid multi-residue method for the quantitative determination and confirmation of glucocorticosteroids in bovine milk using liquid chromatography-electrospray ionization-tandem mass spectrometry.	2007 Apr 4	17386789
Flexor carpi ulnaris tendonopathy in a Weimaraner.	2007 Oct	17903127
A liquid chromatography method using a monolithic column for the determination of corticoids in animal feed and animal feeding water.	2008 Aug	18506427
Optimization of solid phase extraction clean up and validation of quantitative determination of corticosteroids in urine by liquid chromatography-tandem mass spectrometry.	2008 Jun 9	18486661
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 Mar-Apr	19485221
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.	2009 Nov 13	19423120
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.	2010 Apr	20155493
Quantitative determination of corticosteroids in bovine milk using mixed-mode polymeric strong cation exchange solid-phase extraction and liquid chromatography-tandem mass spectrometry.	2010 Dec 1	20643526
Screening and quantitative confirmatory method for the analysis of glucocorticoids in bovine milk using liquid chromatography-tandem mass spectrometry.	2010 Sep-Oct	21140678

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 `Fri Dec 15 16:38:02 GMT 2023` Edited by `admin` on `Fri Dec 15 16:38:02 GMT 2023`
Record UNII	LR3CD8SX89
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUMETHASONE

Official Name

English

FLUMETHASONE [USAN]

Common Name

English

U-10,974

Code

English

NSC-54702

Code

English

6α,9-Difluoro-11β,17,21-trihydroxy-16α-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

Official 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