Flumethasone (CED0012986)

Record Information
Version1.0
Creation Date2016-05-22 05:07:17 UTC
Update Date2026-08-21 22:38:28 UTC
Accession NumberCHEM018271
Identification
Common NameFlumethasone
ClassSmall Molecule
Description
Flumethasone is an organic compound with the chemical formula C22H28F2O5 and an average molecular weight of 410.46 g/mol. Flumethasone belongs to the hydroxysteroids, a subclass of steroids and steroid derivatives within the organic compounds. The compound is found in or released from nine recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it appears in corticosteroids, combinations of corticosteroids with antibiotics, combinations of corticosteroids with antiseptics, antibiotics, and otologicals. In the category of household cleaning and consumer products, it is associated with tobacco smoke filters and non-electric simulated smoking devices. Additionally, it has been recorded in drinking water and water supply, as well as in electrically stimulated smoking devices categorized under electrical and electronic equipment. Recorded exposure routes for the compound include topical, oral, inhalation, and auricular paths. At the molecular level, flumethasone interacts with four recorded protein targets. It acts as an agonist or modulator of the glucocorticoid receptor (NR3C1) and interacts with three steroid hormone receptors: estrogen-related receptor gamma (ESRRG), steroid hormone receptor ERR1 (ESRRA), and steroid hormone receptor ERR2 (ESRRB).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
6alpha,9-Difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dioneChEBI
FlumetasonaChEBI
FlumetasoneChEBI
FlumetasonumChEBI
6a,9-Difluoro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dioneGenerator
6Α,9-difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dioneGenerator
FlumethasoneMeSH
FluorodexamethasoneMeSH
Chemical FormulaC22H28F2O5
Average Molecular Mass410.458 g/mol
Monoisotopic Mass410.190 g/mol
CAS Registry Number2135-17-3
IUPAC Name(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Nameflumethasone
SMILES[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=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
InChI KeyWXURHACBFYSXBI-GQKYHHCASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • 9-halo-steroid
  • 6-halo-steroid
  • Halo-steroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • Halohydrin
  • Fluorohydrin
  • Secondary alcohol
  • Cyclic ketone
  • Organofluoride
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alkyl halide
  • Alkyl fluoride
  • Organooxygen compound
  • Organohalogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.085 g/LALOGPS
logP1.91ALOGPS
logP1.34ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.32 m³·mol⁻¹ChemAxon
Polarizability41.25 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0000900000-ba7d69ed1851790885aaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0079-2891000000-1cedbe5b5cccc84ebdb1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0079-2891000000-1cedbe5b5cccc84ebdb1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-0009300000-4e0a2d6cec87cc743396Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06u6-0119100000-cfc104618dde59580836Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05r9-1097000000-8284008adc103411e662Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0008900000-ed0c57fd99db708ddf46Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-1009100000-24d8d15a9bf87abb6d2bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-7309000000-cc7e650f71665578d80cNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
534.0Log mg/kg[300:950]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
309CorticosteroidsHealthcare, pharmaceuticals & veterinary productsNot Available
310Corticosteroids, combinations with antisepticsHealthcare, pharmaceuticals & veterinary productsNot Available
311Corticosteroids, combinations with antibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
406OtologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)1.40129
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)0.467095
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)2.33548
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.155698
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)2.64687
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)7.23998
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)38.3797
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)8.71911
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)0.155698
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)33.4752
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)45.1525
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)83.2987
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)40.4816
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)1332.86
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)278.0
Phospholipase A2, membrane associated structureClick to view 3D structurePhospholipase A2, membrane associatedP14555HumansPredicted (SEA)39.3917
Protein kinase C epsilon type structureClick to view 3D structureProtein kinase C epsilon typeQ02156HumansPredicted (SEA)452.382
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)480.408
Inhibitor of nuclear factor kappa-B kinase subunit beta structureClick to view 3D structureInhibitor of nuclear factor kappa-B kinase subunit betaO14920HumansPredicted (SEA)1279.3
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)2275.61
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)26.2352
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)2343.65
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)2567.7
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)2602.27
Concentrations
Not Available
External Links
DrugBank IDDB00663
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFlumethasone
Chemspider IDNot Available
ChEBI ID34764
PubChem Compound ID16490
Kegg Compound IDC14479
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References