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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 UTC
HMDB IDHMDB0015181
Secondary Accession Numbers
  • HMDB15181
Metabolite Identification
Common NameFluocinonide
DescriptionFluocinonide is only found in individuals that have used or taken this drug. It is a topical glucocorticoid used in the treatment of eczema. [PubChem]Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. Fluocinonide binds to 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. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.
Structure
Data?1582753267
Synonyms
ValueSource
LidexKegg
VanosKegg
FluocinolideHMDB
Fluocinolide acetateHMDB
Fluocinolone acetonide acetateHMDB
Fluocinonide emulsified baseHMDB
Bioglan brand OF fluocinonideHMDB
FAPG, fluocinonideHMDB
Fluocinolone acetonide 21 acetateHMDB
Medicis brand OF fluocinonideHMDB
NovoterHMDB
Optimapharma brand OF fluocinonideHMDB
TopsynHMDB
Acetonide 21-acetate, fluocinoloneHMDB
Clariana brand OF fluocinonideHMDB
Fluocinolone acetonide 21-acetateHMDB
Fluocinonide fapgHMDB
KlaridermHMDB
LydermHMDB
Grünenthal brand OF fluocinonideHMDB
LidemolHMDB
Syntex brand OF fluocinonideHMDB
TiamolHMDB
Yamanouchi brand OF fluocinonideHMDB
MetosynHMDB
Teofarma brand OF fluocinonideHMDB
TopsymHMDB
TopsyneHMDB
Chemical FormulaC26H32F2O7
Average Molecular Weight494.5249
Monoisotopic Molecular Weight494.211609788
IUPAC Name2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
Traditional Namefluocinonide
CAS Registry Number356-12-7
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)COC(C)=O
InChI Identifier
InChI=1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1
InChI KeyWJOHZNCJWYWUJD-IUGZLZTKSA-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
  • 9-halo-steroid
  • 6-halo-steroid
  • Halo-steroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Delta-1,4-steroid
  • Ketal
  • Alpha-acyloxy ketone
  • Meta-dioxolane
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Halohydrin
  • Carboxylic acid ester
  • Fluorohydrin
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Alkyl halide
  • Carbonyl group
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point309 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.017 g/LNot Available
LogP1.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available229.874http://allccs.zhulab.cn/database/detail?ID=AllCCS00001186
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP2.93ALOGPS
logP2.05ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.55ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity120.56 m³·mol⁻¹ChemAxon
Polarizability49.12 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-241.81730932474
DeepCCS[M+Na]+216.15530932474
AllCCS[M+H]+212.132859911
AllCCS[M+H-H2O]+210.432859911
AllCCS[M+NH4]+213.732859911
AllCCS[M+Na]+214.132859911
AllCCS[M-H]-214.132859911
AllCCS[M+Na-2H]-215.632859911
AllCCS[M+HCOO]-217.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Fluocinonide[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)COC(C)=O3901.9Standard polar33892256
Fluocinonide[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)COC(C)=O2973.1Standard non polar33892256
Fluocinonide[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)COC(C)=O3726.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluocinonide,1TMS,isomer #1CC(=O)OCC(=O)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]12C3199.0Semi standard non polar33892256
Fluocinonide,1TMS,isomer #2CC(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]12C3311.3Semi standard non polar33892256
Fluocinonide,2TMS,isomer #1CC(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]12C3249.1Semi standard non polar33892256
Fluocinonide,2TMS,isomer #1CC(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]12C3369.3Standard non polar33892256
Fluocinonide,2TMS,isomer #1CC(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]12C3721.3Standard polar33892256
Fluocinonide,1TBDMS,isomer #1CC(=O)OCC(=O)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C3434.6Semi standard non polar33892256
Fluocinonide,1TBDMS,isomer #2CC(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]12C3533.7Semi standard non polar33892256
Fluocinonide,2TBDMS,isomer #1CC(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C3696.7Semi standard non polar33892256
Fluocinonide,2TBDMS,isomer #1CC(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C3806.6Standard non polar33892256
Fluocinonide,2TBDMS,isomer #1CC(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C)(C)O[C@@H]1C[C@H]1[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C3863.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fluocinonide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-2970300000-b28abd90df71a08d58302017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluocinonide GC-MS (1 TMS) - 70eV, Positivesplash10-0uxv-8826190000-2fbadbdcb0a9e253ca762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluocinonide 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 - Fluocinonide LC-ESI-qTof , Positive-QTOFsplash10-05p9-0489400000-cb64b15c0db3ac6d96472017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluocinonide , positive-QTOFsplash10-05p9-0489400000-cb64b15c0db3ac6d96472017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 10V, Positive-QTOFsplash10-002k-1000900000-e5fb75b78cc935feaae52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 20V, Positive-QTOFsplash10-000i-0131900000-536fef6403492e1fa2c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 40V, Positive-QTOFsplash10-06vl-3090100000-1ba50606e9f8460db6f92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 10V, Negative-QTOFsplash10-052f-9004700000-80b0fde09a680751d47d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 20V, Negative-QTOFsplash10-0a4i-9001300000-af17f3d6e24dac3b4d872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 40V, Negative-QTOFsplash10-0a4i-9103000000-dc678ae7667181f4963f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 10V, Positive-QTOFsplash10-002b-0002900000-e3fc2590054d37633c942021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 20V, Positive-QTOFsplash10-00mk-0011900000-363237e4357a441d0fa02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 40V, Positive-QTOFsplash10-0006-2593700000-aa24051f16cec875596c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 10V, Negative-QTOFsplash10-052f-3000900000-ae14e057a2b93ea326662021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluocinonide 40V, Negative-QTOFsplash10-0a4l-9300200000-d5906f7ea807d5bbb4d82021-10-11Wishart 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 DB01047 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01047 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01047
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9265
KEGG Compound IDC07007
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluocinonide
METLIN IDNot Available
PubChem Compound9642
PDB IDNot Available
ChEBI ID519542
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.