Fluorometholone (CHEM019546)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:16:13 UTC
Update Date2016-11-09 01:16:01 UTC
Accession NumberCHEM019546
Identification
Common NameFluorometholone
ClassSmall Molecule
DescriptionA glucocorticoid employed, usually as eye drops, in the treatment of allergic and inflammatory conditions of the eye. It has also been used topically in the treatment of various skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732)
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
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 Solubility0.017 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
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, Positivesplash10-01qd-2923000000-d51e17b0fa8439e2bc18Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-4646090000-fd4d299c79b87e200eeaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0079-2960000000-57c1831d283834b32701Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0079-2960000000-57c1831d283834b32701Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-059i-2930000000-4f8bf4616616ac38dbe2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0079-0950000000-553575697067e4b2ea74Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-002r-0691000000-e9d333f14892b5c60042Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004r-0394000000-2093403203c2b0fc9c10Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0avu-2920000000-7eaf4c211285e06ae8ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-059i-2930000000-c99fa5c5e166ee859f74Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00kf-3910000000-b4846c764fd5be25b954Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0980000000-b0a88a5603fd3efe6849Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-002r-0791000000-77abf92c461f1ad29d3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-000i-1960000000-4594ec630c6854d76672Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-009i-0389000000-cf127fcfcee4a744f76aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0079-0950000000-362de078c079eaec2b48Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-186c4dfe4b7e61670d08Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004r-0394000000-07ae4bf52b68e15af517Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0980000000-c3c01780614bd50c5d7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-002r-0691000000-55e76cdcb25ab8d35c0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-531774f624efd22f7096Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-0129000000-87f7ef0f82ebc7d60851Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008i-0392000000-d6c8be250e0763166290Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-e9871ab3d4408fc89668Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05rr-0009000000-edd2f8db34c792d235cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldr-0129000000-09e9dc7990d339033e84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-44db180c7fb54e31ed64Spectrum
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 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