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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:40:01 UTC
HMDB IDHMDB0014469
Secondary Accession Numbers
  • HMDB14469
Metabolite Identification
Common NameFluorometholone
DescriptionFluorometholone is only found in individuals that have used or taken this drug. It is a 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)There is no generally accepted explanation for the mechanism of action of ocular corticosteroids. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Their primary target is the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes.
Structure
Data?1582753183
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 Weight376.4617
Monoisotopic Molecular Weight376.204987621
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
CAS Registry Number426-13-1
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 Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point297 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.017 g/LNot Available
LogP2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP10(2.34) g/LALOGPS
logP10(2.42) g/LChemAxon
logS10(-4.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Fluorometholone[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@]12C4017.4Standard polar33892256
Fluorometholone[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@]12C2730.6Standard non polar33892256
Fluorometholone[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@]12C2929.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluorometholone,1TMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3116.8Semi standard non polar33892256
Fluorometholone,1TMS,isomer #2CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3048.0Semi standard non polar33892256
Fluorometholone,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3026.0Semi standard non polar33892256
Fluorometholone,2TMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3034.4Semi standard non polar33892256
Fluorometholone,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3017.0Semi standard non polar33892256
Fluorometholone,2TMS,isomer #3C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C2931.5Semi standard non polar33892256
Fluorometholone,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C2964.4Semi standard non polar33892256
Fluorometholone,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3055.7Standard non polar33892256
Fluorometholone,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3254.3Standard polar33892256
Fluorometholone,1TBDMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3347.6Semi standard non polar33892256
Fluorometholone,1TBDMS,isomer #2CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3288.8Semi standard non polar33892256
Fluorometholone,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3259.0Semi standard non polar33892256
Fluorometholone,2TBDMS,isomer #1CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3495.7Semi standard non polar33892256
Fluorometholone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3476.3Semi standard non polar33892256
Fluorometholone,2TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3397.0Semi standard non polar33892256
Fluorometholone,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3634.4Semi standard non polar33892256
Fluorometholone,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3703.8Standard non polar33892256
Fluorometholone,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3482.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fluorometholone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qd-2923000000-d51e17b0fa8439e2bc182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorometholone GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-4646090000-fd4d299c79b87e200eea2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorometholone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone LC-ESI-qTof , Positive-QTOFsplash10-0079-2960000000-57c1831d283834b327012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone , positive-QTOFsplash10-0079-2960000000-57c1831d283834b327012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 60V, Positive-QTOFsplash10-059i-2930000000-4f8bf4616616ac38dbe22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 50V, Positive-QTOFsplash10-0079-0950000000-553575697067e4b2ea742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 30V, Positive-QTOFsplash10-002r-0691000000-e9d333f14892b5c600422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 20V, Positive-QTOFsplash10-004r-0394000000-2093403203c2b0fc9c102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 75V, Positive-QTOFsplash10-0avu-2920000000-7eaf4c211285e06ae8cc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 60V, Positive-QTOFsplash10-059i-2930000000-c99fa5c5e166ee859f742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 90V, Positive-QTOFsplash10-00kf-3910000000-b4846c764fd5be25b9542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 40V, Positive-QTOFsplash10-01p9-0980000000-b0a88a5603fd3efe68492021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 30V, Positive-QTOFsplash10-002r-0791000000-77abf92c461f1ad29d3b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 45V, Positive-QTOFsplash10-000i-1960000000-4594ec630c6854d766722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 15V, Positive-QTOFsplash10-009i-0389000000-cf127fcfcee4a744f76a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 50V, Positive-QTOFsplash10-0079-0950000000-362de078c079eaec2b482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 10V, Positive-QTOFsplash10-004i-0019000000-186c4dfe4b7e61670d082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 20V, Positive-QTOFsplash10-004r-0394000000-07ae4bf52b68e15af5172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 40V, Positive-QTOFsplash10-01p9-0980000000-c3c01780614bd50c5d7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorometholone 30V, Positive-QTOFsplash10-002r-0691000000-55e76cdcb25ab8d35c0c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorometholone 10V, Positive-QTOFsplash10-056r-0009000000-531774f624efd22f70962016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorometholone 20V, Positive-QTOFsplash10-0a6u-0129000000-87f7ef0f82ebc7d608512016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorometholone 40V, Positive-QTOFsplash10-008i-0392000000-d6c8be250e07631662902016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorometholone 10V, Negative-QTOFsplash10-004i-0009000000-e9871ab3d4408fc896682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorometholone 20V, Negative-QTOFsplash10-05rr-0009000000-edd2f8db34c792d235cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorometholone 40V, Negative-QTOFsplash10-0ldr-0129000000-09e9dc7990d339033e842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorometholone 10V, Positive-QTOFsplash10-056r-0009000000-44db180c7fb54e31ed642021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00324 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00324 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00324
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9494
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluorometholone
METLIN IDNot Available
PubChem Compound9878
PDB IDNot Available
ChEBI ID31625
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. El-Sankary W, Bombail V, Gibson GG, Plant N: Glucocorticoid-mediated induction of CYP3A4 is decreased by disruption of a protein: DNA interaction distinct from the pregnane X receptor response element. Drug Metab Dispos. 2002 Sep;30(9):1029-34. [PubMed:12167569 ]