Fluorometholone (CED0005823)

Record Information
Version1.0
Creation Date2016-05-22 06:16:13 UTC
Update Date2026-08-21 22:47:54 UTC
Accession NumberCHEM019546
Identification
Common NameFluorometholone
ClassSmall Molecule
Description
Fluorometholone is an organic compound with the chemical formula C22H29FO4 and an average molecular weight of 376.46 g/mol. Fluorometholone belongs to the pregnane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This compound acts as an agonist of the Glucocorticoid receptor (NR3C1). It has been recorded in 30 different sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized in corticosteroids, corticosteroids combined with antibiotics, anti-acne preparations, antiinflammatory agents, and vasoprotectives. It is also associated with household cleaning and consumer products, including tobacco smoke filters, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in food, food processing, and cookware contexts, specifically in the preparation of vinegar, the preparation of wine or sparkling wine, food preservation, and fermentation processes for beer. Other recorded sources include electrical and electronic equipment, such as antennas, amplifiers, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, and electric hearing aids. The recorded exposure route for this compound is ophthalmic.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
9-Fluoro-11beta,17-dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dioneChEBI
Fluor-OPChEBI
FluorometholonChEBI
FluorometholonumChEBI
FluorometolonaChEBI
NSC 33001ChEBI
OxyloneChEBI
FmlKegg
9-Fluoro-11b,17-dihydroxy-6a-methylpregna-1,4-diene-3,20-dioneGenerator
9-Fluoro-11β,17-dihydroxy-6α-methylpregna-1,4-diene-3,20-dioneGenerator
FluormetholonHMDB
FluormetholoneHMDB
FluoromethaloneHMDB
Fluor OPHMDB
Fluoro ophtalHMDB
Pharm-allergan brand OF fluorometholoneHMDB
Pharmascience brand OF fluorometholoneHMDB
Ursapharm brand OF fluorometholoneHMDB
CortisdinHMDB
EfflumidexHMDB
FML ForteHMDB
Fluoro-ophtalHMDB
Isopto fluconHMDB
PMS FluorometholoneHMDB
PMS-FluorometholoneHMDB
Pharm allergan brand OF fluorometholoneHMDB
Allergan brand 1 OF fluorometholoneHMDB
Allergan brand 2 OF fluorometholoneHMDB
FML LiquifilmHMDB
Flucon, isoptoHMDB
FluoroposHMDB
Winzer brand OF fluorometholoneHMDB
Alcon brand OF fluorometholoneHMDB
Allergan brand 3 OF fluorometholoneHMDB
FluconHMDB
Isdin brand OF fluorometholoneHMDB
Novartis brand OF fluorometholoneHMDB
Chemical FormulaC22H29FO4
Average Molecular Mass376.462 g/mol
Monoisotopic Mass376.205 g/mol
CAS Registry Number426-13-1
IUPAC Name(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Namefluorometholone
SMILES[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1
InChI KeyFAOZLTXFLGPHNG-KNAQIMQKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 9-halo-steroid
  • Halo-steroid
  • Hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • 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 Solubility0.017 g/LALOGPS
logP2.34ALOGPS
logP2.42ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.65ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity100.87 m³·mol⁻¹ChemAxon
Polarizability40.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01qd-2923000000-d51e17b0fa8439e2bc18Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-4646090000-fd4d299c79b87e200eeaNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0079-2960000000-57c1831d283834b32701Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0079-2960000000-57c1831d283834b32701Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-059i-2930000000-4f8bf4616616ac38dbe2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0079-0950000000-553575697067e4b2ea74Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0691000000-e9d333f14892b5c60042Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0394000000-2093403203c2b0fc9c10Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0avu-2920000000-7eaf4c211285e06ae8ccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-059i-2930000000-c99fa5c5e166ee859f74Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-3910000000-b4846c764fd5be25b954Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01p9-0980000000-b0a88a5603fd3efe6849Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0791000000-77abf92c461f1ad29d3bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-1960000000-4594ec630c6854d76672Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-009i-0389000000-cf127fcfcee4a744f76aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0079-0950000000-362de078c079eaec2b48Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0019000000-186c4dfe4b7e61670d08Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0394000000-07ae4bf52b68e15af517Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01p9-0980000000-c3c01780614bd50c5d7cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0691000000-55e76cdcb25ab8d35c0cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0009000000-531774f624efd22f7096Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6u-0129000000-87f7ef0f82ebc7d60851Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-008i-0392000000-d6c8be250e0763166290Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-e9871ab3d4408fc89668Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05rr-0009000000-edd2f8db34c792d235cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ldr-0129000000-09e9dc7990d339033e84Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0009000000-44db180c7fb54e31ed64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-0849000000-992b66728304cd06e16cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9563000000-399cb6a7b908acc6bffeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-18f5c36db48c93499583Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-0009000000-c3e977ef5fa4c46fa70fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001r-0239000000-eab1a1ea50fcf7f1ba78Not 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
666.0Log mg/kg[370:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
292VasoprotectivesHealthcare, pharmaceuticals & veterinary productsNot Available
309CorticosteroidsHealthcare, pharmaceuticals & veterinary productsNot Available
311Corticosteroids, combinations with antibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
314Anti-acne preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
396Antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
397Antiinflammatory agents and antiinfectives in combinationHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)2.72472
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)0.544945
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)4.43741
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)14.9471
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)4.12601
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.389246
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)15.1027
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)20.4743
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)121.056
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)46.5538
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)69.0523
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)20.3186
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)19.6959
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)0.467095
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)100.27
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)23.1991
Click to view 3D structureGlucocorticoid receptorP06537Mus musculusPredicted (SEA)6.85073
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)4641.99
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)136.548
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)759.419
Click to view 3D structureNeurogenic locus notch homolog protein 1Q01705Mus musculusPredicted (SEA)1.47914
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)40.6373
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)353.825
Click to view 3D structureSex hormone-binding globulinP08689Rattus norvegicusPredicted (SEA)13.5458
Concentrations
Not Available
External Links
DrugBank IDDB00324
HMDB IDHMDB0014469
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluorometholone
Chemspider ID9494
ChEBI ID31625
PubChem Compound ID9878
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22821643
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23023407
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23225837
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23429038
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23865053
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24074291
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24227962
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24493163