Fluocinolone acetonide (CED0005793)

Record Information
Version1.0
Creation Date2016-05-22 04:28:13 UTC
Update Date2026-08-22 03:48:17 UTC
Accession NumberCHEM017572
Identification
Common NameFluocinolone acetonide
ClassSmall Molecule
Description
Fluocinolone acetonide (C24H30F2O6) is a chemical compound with an average molecular weight of 452.49 g/mol. Fluocinolone acetonide belongs to the hydroxysteroids, a subclass of steroids and steroid derivatives within the organic compounds. The compound is found in or released from 31 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized in antiinflammatory agents, vasoprotectives, and corticosteroids, including corticosteroid combinations with antibiotics and antiseptics. Other recorded sources include food preservation in food, food processing and cookware; household cleaning and consumer products such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices; and electrical and electronic equipment, including antennas, amplifiers, communication cables or conductors, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for this compound include oral, topical, auricular, inhalation, intraocular, and intravitreal. Fluocinolone acetonide interacts with seven recorded protein targets. It acts as an agonist, inducer, or inhibitor of the glucocorticoid receptor (NR3C1), as well as Annexin A1 (ANXA1), Annexin A2 (ANXA2), Annexin A3 (ANXA3), and three other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
6alpha,9alpha-Difluoro-16alpha-hydroxyprednisolone 16,17-acetonideChEBI
6alpha-Fluorotriamcinolone acetonideChEBI
Acetonide de fluocinoloneChEBI
Acetonido de fluocinolonaChEBI
CoriphateChEBI
CortiplastolChEBI
Derma-smoothe/fsChEBI
DermalarChEBI
FlucinarChEBI
FlucortChEBI
FluocetChEBI
Fluocinolone 16,17-acetonideChEBI
Fluocinoloni acetonidumChEBI
FluonidChEBI
FluotrexChEBI
FluovitifChEBI
FlupollonChEBI
FluzonChEBI
IluvienChEBI
JellinChEBI
LocalynChEBI
OmnidermChEBI
PercutinaChEBI
ProderminChEBI
RadiocinChEBI
RetisertChEBI
SinalarChEBI
SynalarChEBI
SynamolChEBI
SynandoneChEBI
SynandroneChEBI
SynemolChEBI
SynoticChEBI
SynsacChEBI
TefunoteChEBI
6a,9a-Difluoro-16a-hydroxyprednisolone 16,17-acetonideGenerator
6Α,9α-difluoro-16α-hydroxyprednisolone 16,17-acetonideGenerator
6a-Fluorotriamcinolone acetonideGenerator
6Α-fluorotriamcinolone acetonideGenerator
Coriphic acidGenerator
FlucinoloneHMDB
FluocinolonacetonidumHMDB
Acetonide, fluocinoloneHMDB
Allergan brand OF fluocinolone acetonideHMDB
CO-FluocinHMDB
FS, Derma-smoothHMDB
Fluortriamcinolone acetonideHMDB
FlurosynHMDB
Galderma brand OF fluocinolone acetonideHMDB
Medicis brand 2 OF fluocinolone acetonideHMDB
Synalar HPHMDB
Acetonide, fluortriamcinoloneHMDB
AlvadermoHMDB
CapexHMDB
Derma smooth FSHMDB
FluocidHMDB
Geni brand OF fluocinolone acetonideHMDB
Grünenthal brand OF fluocinolone acetonideHMDB
Hill brand OF fluocinolone acetonideHMDB
Rugby brand OF fluocinolone acetonideHMDB
Savage brand OF fluocinolone acetonideHMDB
Septa brand OF fluocinolone acetonideHMDB
Bioglan brand OF fluocinolone acetonideHMDB
Centrum brand OF fluocinolone acetonideHMDB
Co fluocinHMDB
Derma-smooth FSHMDB
FluodermoHMDB
GelidinaHMDB
Inkeysa brand OF fluocinolone acetonideHMDB
JellisoftHMDB
Medicis brand 1 OF fluocinolone acetonideHMDB
Smaller brand OF fluocinolone acetonideHMDB
Synalar-HPHMDB
Syntex brand OF fluocinolone acetonideHMDB
Yamanouchi brand OF fluocinolone acetonideHMDB
Medphano brand OF fluocinolone acetonideHMDB
CortiespecHMDB
FlusolgenHMDB
Inexfa brand OF fluocinolone acetonideHMDB
Chemical FormulaC24H30F2O6
Average Molecular Mass452.488 g/mol
Monoisotopic Mass452.201 g/mol
CAS Registry Number67-73-2
IUPAC Name(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one
Traditional Namecapex
SMILES[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO
InChI IdentifierInChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
InChI KeyFEBLZLNTKCEFIT-VSXGLTOVSA-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
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 9-halo-steroid
  • 6-halo-steroid
  • Halo-steroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Delta-1,4-steroid
  • Ketal
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Meta-dioxolane
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Organofluoride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Alkyl fluoride
  • Alcohol
  • Organohalogen compound
  • Alkyl halide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.055 g/LALOGPS
logP2.47ALOGPS
logP1.6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.35ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity111.41 m³·mol⁻¹ChemAxon
Polarizability44.97 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4u-2790300000-f726c5edd782f086d667Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-1312190000-3d4982ca2270e0fc9e78Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0il9-0496400000-d158ff1b8dbcf078b8ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3981000000-e34007db14fcd7363a09Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0il9-0496400000-d158ff1b8dbcf078b8ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3981000000-e34007db14fcd7363a09Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-0001900000-1b554128715f86bd3c32Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0k9l-2165900000-237d73e29007e691d6d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0c29-1091100000-6ed7a376ae3c8b2fd2dfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1004900000-628e9b1a1feff59435e4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kal-2004900000-7ffae0e5a19cb29f3732Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-6219000000-0de5fc8aacf929dedc54Not 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
46.0Log mg/kg[30:83]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
292VasoprotectivesHealthcare, pharmaceuticals & veterinary productsNot 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
396Antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
397Antiinflammatory agents and antiinfectives in combinationHealthcare, pharmaceuticals & veterinary productsNot Available
406OtologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
515Discharge Tubes With Liquid Pool CathodesElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, 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
563Soap DetergentsHousehold 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
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot 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
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
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)93.2634
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)25.301
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)97.7786
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)0.467095
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)159.747
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)31.6068
Inhibitor of nuclear factor kappa-B kinase subunit beta structureClick to view 3D structureInhibitor of nuclear factor kappa-B kinase subunit betaO14920HumansPredicted (SEA)3860.23
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)1822.53
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)1765.93
Protein kinase C epsilon type structureClick to view 3D structureProtein kinase C epsilon typeQ02156HumansPredicted (SEA)2761.16
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)3049.2
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)5423.68
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)5854.73
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)5877.85
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)5869.13
Inhibitor of nuclear factor kappa-B kinase subunit alpha structureClick to view 3D structureInhibitor of nuclear factor kappa-B kinase subunit alphaO15111HumansPredicted (SEA)4271.66
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)1.63483
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)0.389246
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)5.2159
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)6.77288
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.389246
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)25.6902
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)4.9045
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)14.6357
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.155698
Concentrations
Not Available
External Links
DrugBank IDDB00591
HMDB IDHMDB0014729
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluocinolone_acetonide
Chemspider ID5980
ChEBI ID31623
PubChem Compound ID6215
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jaffe GJ, Yang CH, Guo H, Denny JP, Lima C, Ashton P: Safety and pharmacokinetics of an intraocular fluocinolone acetonide sustained delivery device. Invest Ophthalmol Vis Sci. 2000 Oct;41(11):3569-75.
2. Brumm MV, Nguyen QD: Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. Int J Nanomedicine. 2007;2(1):55-64.
3. Goldstein DA, Godfrey DG, Hall A, Callanan DG, Jaffe GJ, Pearson PA, Usner DW, Comstock TL: Intraocular pressure in patients with uveitis treated with fluocinolone acetonide implants. Arch Ophthalmol. 2007 Nov;125(11):1478-85. Epub 2007 Oct 8.
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. 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.
6. 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.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. The lipid handbook with CD-ROM
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21238799
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21277557
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21459216
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23321234
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23323586