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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 of FLUMETHASONE

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

Description
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

1969
24
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
LOCORTEN

Approved Use

This medication is used in corticosteroid-responsive dermatoses.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

OverviewOther

Other InhibitorOther SubstrateOther Inducer
11-beta-HSD1
12

11-beta-HSD2
27
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
11-beta-HSD1
12
 yes
11-beta-HSD2
27
 yes
CYP3A4
1737
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
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
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
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
Confirmation of synthetic glucocorticoids with liquid chromatography/mass spectrometry: organization and results of an international interlaboratory comparison test.
2005 Jan-Feb
A simple and rapid ESI-LC-MS/MS method for simultaneous screening of doping agents in urine samples.
2009 Apr
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.
2009 Nov 13
Pivotal Advance: Pharmacological manipulation of inflammation resolution during spontaneously resolving tissue neutrophilia in the zebrafish.
2010 Feb
Patents

Patents

EP1395603B1
2
US6528666
3
WO2002100878A1
2

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
Name Type Language
FLUMETHASONE
GREEN BOOK   MI   USAN  
USAN  
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
INN   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-VATC QD07CB05
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-VATC QD07BB01
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-VATC QD07XB01
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
CFR 21 CFR 522.960A
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
CFR 21 CFR 520.960
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-ATC D07AB03
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-VATC QS02CA02
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-ATC D07CB05
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
NCI_THESAURUS C521
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
CFR 21 CFR 522.960
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
CFR 21 CFR 522.960C
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-ATC D07XB01
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-VATC QD07AB03
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-ATC S02CA02
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
CFR 21 CFR 524.960
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
WHO-VATC QH02AB90
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
218-370-9
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
CHEBI
34764
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
DRUG CENTRAL
4548
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID2045365
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
NSC
54702
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
RXCUI
4458
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY RxNorm
CHEBI
31623
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
SMS_ID
100000080687
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
CAS
2135-17-3
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
FDA UNII
LR3CD8SX89
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
WIKIPEDIA
FLUMETASONE
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
EVMPD
SUB07698MIG
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201392
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
MERCK INDEX
m5439
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY Merck Index
PUBCHEM
16490
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
DAILYMED
LR3CD8SX89
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
DRUG BANK
DB00663
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
NCI_THESAURUS
C65717
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
INN
1355
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
MESH
D005443
Created by admin on Fri Dec 15 16:38:02 UTC 2023 , Edited by admin on Fri Dec 15 16:38:02 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of FLUMETHASONE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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