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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H36F2O6
Molecular Weight 494.5679
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUMETHASONE PIVALATE

SMILES

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)COC(=O)C(C)(C)C)[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=JWRMHDSINXPDHB-OJAGFMMFSA-N
InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/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
Accelerated solvent extraction and liquid chromatography-tandem mass spectrometry quantitation of corticosteroid residues in bovine liver.
2001 Apr 5
Determination of flumethasone in calf urine and serum by liquid chromatography-tandem mass spectrometry.
2001 May 5
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
Development of a dual luciferase reporter screening assay for the detection of synthetic glucocorticoids in animal tissues.
2003 Dec
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
Otic drops used to clear a blocked grommet: an in vitro prospective randomized controlled study with blinded assessment.
2004 Dec
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
Regression of subcorneal pustular dermatosis type of IgA pemphigus lesions with azithromycin.
2005 Aug
G-protein-coupled glucocorticoid receptors on the pituitary cell membrane.
2005 Aug 1
Confirmation of synthetic glucocorticoids with liquid chromatography/mass spectrometry: organization and results of an international interlaboratory comparison test.
2005 Jan-Feb
Effect of steroidal and non-steroidal anti-inflammatory drugs on inflammatory markers in calves with experimentally-induced bronchopneumonia.
2005 Jul-Aug
Detection of synthetic corticosteroids in bovine urine by chemiluminescence high-performance liquid chromatography.
2005 May-Jun
A chromatography method for the screening and confirmatory detection of dexamethasone.
2006 Dec
Medical treatment of vulvar squamous cell hyperplasia.
2006 Dec
Effect of selected fluorinated drugs in a "ringing" gel on rheological behaviour and skin permeation.
2007 Apr
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
High throughput HPLC-ESI-MS method for the quantitation of dexamethasone in blood plasma.
2007 Jan 4
Flexor carpi ulnaris tendonopathy in a Weimaraner.
2007 Oct
A liquid chromatography method using a monolithic column for the determination of corticoids in animal feed and animal feeding water.
2008 Aug
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
A simple and rapid ESI-LC-MS/MS method for simultaneous screening of doping agents in urine samples.
2009 Apr
Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry.
2009 Apr 1
Lecithin based nanoemulsions: A comparative study of the influence of non-ionic surfactants and the cationic phytosphingosine on physicochemical behaviour and skin permeation.
2009 Mar 31
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
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.
2009 Nov 13
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
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
Simultaneous determination of corticosteroids, androgens, and progesterone in river water by liquid chromatography-tandem mass spectrometry.
2010 Feb
Pivotal Advance: Pharmacological manipulation of inflammation resolution during spontaneously resolving tissue neutrophilia in the zebrafish.
2010 Feb
Quantification of corticosteroids in bovine urine using selective solid phase extraction and reversed-phase liquid chromatography/tandem mass spectrometry.
2010 Jun 1
Screening and quantitative confirmatory method for the analysis of glucocorticoids in bovine milk using liquid chromatography-tandem mass spectrometry.
2010 Sep-Oct
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 PIVALATE
ORANGE BOOK   USAN   USP   USP-RS  
USAN  
Official Name English
FLUMETHASONE PIVALATE [USP IMPURITY]
Common Name English
FLUMETASONE PIVALATE [JAN]
Common Name English
FLUMETHASONE PIVALATE [USAN]
Common Name English
FLUMETHASONE PIVALATE [ORANGE BOOK]
Common Name English
6α,9-Difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-pivalate
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 21-(2,2-DIMETHYL-1-OXOPROPOXY)-6,9-DIFLUORO-11,17-DIHYDROXY-16-METHYL-, (6.ALPHA.,11.BETA.,16.ALPHA.)
Common Name English
Flumetasone pivalate [WHO-DD]
Common Name English
FLUMETASONE PIVALATE [MART.]
Common Name English
FLUMETASONE PIVALATE [EP MONOGRAPH]
Common Name English
LOCORTEN
Code English
NSC-107680
Code English
FLUMETASONE PIVALATE
MART.   WHO-DD  
Common Name English
FLUMETHASONE 21-PIVALATE [MI]
Common Name English
FLUMETHASONE 21-PIVALATE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID7049005
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
IUPHAR
7075
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
PUBCHEM
443980
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
ECHA (EC/EINECS)
217-901-1
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
EVMPD
SUB02212MIG
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
FDA UNII
0DV09X6F21
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
DRUG CENTRAL
1198
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
CHEBI
31620
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200877
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
RXCUI
25113
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
Flumetasone pivalate
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
SMS_ID
100000089826
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
MERCK INDEX
m5439
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C65718
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
CAS
2002-29-1
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
MESH
C005565
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
DRUG BANK
DBSALT001004
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
NSC
107680
Created by admin on Fri Dec 15 15:02:46 UTC 2023 , Edited by admin on Fri Dec 15 15:02:46 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of FLUMETHASONE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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