Fluocinolone acetonide (CHEM017572)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:28:13 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017572
Identification
Common NameFluocinolone acetonide
ClassSmall Molecule
DescriptionFluocinolone acetonide, with the formula 6-alpha, 9-alpha-difluoro-16-alpha, 17 alpha-acetonide, is a corticosteroid that presents a high lipophilicity. It has been used extensively in dermatological preparations and it has also been investigated thoroughly for its use in implantable corticosteroid devices. This type of device containing fluocinolone acetonide was developed by Taro Pharmaceuticals and approved by FDA in May 2016.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-2790300000-f726c5edd782f086d667Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1312190000-3d4982ca2270e0fc9e78Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0il9-0496400000-d158ff1b8dbcf078b8ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-3981000000-e34007db14fcd7363a09Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0il9-0496400000-d158ff1b8dbcf078b8ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-3981000000-e34007db14fcd7363a09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0001900000-1b554128715f86bd3c32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9l-2165900000-237d73e29007e691d6d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c29-1091100000-6ed7a376ae3c8b2fd2dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1004900000-628e9b1a1feff59435e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kal-2004900000-7ffae0e5a19cb29f3732Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6219000000-0de5fc8aacf929dedc54Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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