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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-17 11:04:32 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005036
Secondary Accession Numbers
  • HMDB0014726
  • HMDB05036
  • HMDB14726
Metabolite Identification
Common NameFluticasone propionate
DescriptionFluticasone propionate, a medium-potency synthetic corticosteroid, is used topically to relieve inflammatory and pruritic symptoms of dermatoses and psoriasis, intranasally to manage symptoms of allergic and non-allergic rhinitis, and orally for the treatment of asthma. Fluticasone propionate binds to the glucocorticoid receptor. Unbound corticosteroids cross the membranes of cells such as mast cells and eosinophils, binding with high affinity to glucocorticoid receptors (GR). The results include alteration of transcription and protein synthesis, a decreased release of leukocytic acid hydrolases, reduction in fibroblast proliferation, prevention of macrophage accumulation at inflamed sites, reduction of collagen deposition, interference with leukocyte adhesion to the capillary wall, reduction of capillary membrane permeability and subsequent edema, reduction of complement components, inhibition of histamine and kinin release, and interference with the formation of scar tissue. In the management of asthma, the glucocorticoid receptor complexes down-regulates proinflammatory mediators such as interleukin-(IL)-1, 3, and 5, and up-regulates anti-inflammatory mediators such as IκB (inhibits NF-κB). Corticosteroids are the most effective anti-inflammatory therapy for allergic diseases. They are believed to inhibit T helper cell type 2 (TH2 T-cell) activation through increased immunoregulatory T cell (CD4+CD25+) suppression (PMID: 15316506 ). Fluticasone propionate is marketed under the brand name Flixotide and Flixonase by Allen & Hanburys, and Flovent and Flonase by GlaxoSmithKline. Fluticasone propionate is only found in individuals that have used or taken this drug.
Structure
Data?1582752342
Synonyms
ValueSource
CutivateChEBI
FlonaseKegg
FloventKegg
Cutivic acidGenerator
Fluticasone propionic acidGenerator
Flovent diskus 250HMDB
Flovent diskus 50HMDB
CCI-18781cutivATEHMDB
Flovent diskus 100HMDB
Flovent hfaHMDB
FLUTICASONEHMDB
CCI 18781HMDB
CCI-18781cutivic acidHMDB
AsmatilHMDB
AxotideHMDB
BrethalHMDB
CultivateHMDB
FlixonaseHMDB
Flixonase nasal sprayHMDB
FlixotideHMDB
Flixotide diskHMDB
Flixotide disksHMDB
Flixotide inhalerHMDB
Flovent diskusHMDB
Flovent rotadiskHMDB
FluinolHMDB
FlunaseHMDB
FlusonalHMDB
FluspiralHMDB
Fluticasonpropionat allenHMDB
FlutideHMDB
FlutivateHMDB
HFA, floventHMDB
Propionate, fluticasoneHMDB
Chemical FormulaC25H31F3O5S
Average Molecular Weight500.571
Monoisotopic Molecular Weight500.184429407
IUPAC Name(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
Traditional Name(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
CAS Registry Number80474-14-2
SMILES
[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/m1/s1
InChI KeyWMWTYOKRWGGJOA-CENSZEJFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxosteroid
  • Hydroxysteroid
  • 6-halo-steroid
  • 9-halo-steroid
  • Oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Halo-steroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Halohydrin
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Thiocarboxylic acid ester
  • Fluorohydrin
  • Cyclic ketone
  • Carbothioic s-ester
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Thiocarboxylic acid or derivatives
  • Monocarboxylic acid or derivatives
  • Organosulfur compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alkyl halide
  • Alkyl fluoride
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.69ALOGPS
logP3.72ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.56ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.65 m³·mol⁻¹ChemAxon
Polarizability49.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-243.09530932474
DeepCCS[M+Na]+218.35830932474
AllCCS[M+H]+211.532859911
AllCCS[M+H-H2O]+209.932859911
AllCCS[M+NH4]+213.132859911
AllCCS[M+Na]+213.532859911
AllCCS[M-H]-211.032859911
AllCCS[M+Na-2H]-212.432859911
AllCCS[M+HCOO]-214.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Fluticasone propionate[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C3881.9Standard polar33892256
Fluticasone propionate[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C3157.6Standard non polar33892256
Fluticasone propionate[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C3410.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluticasone propionate,1TMS,isomer #1CCC(=O)O[C@]1(C(=O)SCF)[C@H](C)C[C@H]2[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@@]21C3233.5Semi standard non polar33892256
Fluticasone propionate,1TBDMS,isomer #1CCC(=O)O[C@]1(C(=O)SCF)[C@H](C)C[C@H]2[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@@]21C3459.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fluticasone propionate GC-MS (Non-derivatized) - 70eV, Positivesplash10-005i-8973700000-7ae41b4f0c6c911755562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluticasone propionate GC-MS (1 TMS) - 70eV, Positivesplash10-1003-4319060000-b20ab3b8b6ed86e8912c2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate , positive-QTOFsplash10-03dl-0497100000-b64248896abdef386eaf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 50V, Positive-QTOFsplash10-0200-0790000000-4d8a865f47a79975f30a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 40V, Positive-QTOFsplash10-004i-0490000000-00982c202544f0c432e32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 50V, Positive-QTOFsplash10-0200-0790000000-9312e39ae770e7245a532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 30V, Positive-QTOFsplash10-004l-0392000000-35466d5bb70b1d6f16342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 20V, Positive-QTOFsplash10-01ox-0197000000-044d3734659c98c68da22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 10V, Positive-QTOFsplash10-0udi-0025290000-848a15088230876c18182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 30V, Positive-QTOFsplash10-004l-0392000000-01368c6428b545907e1c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluticasone propionate 40V, Positive-QTOFsplash10-004i-0490000000-0fd22d1ac4b72bdebc1f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 10V, Positive-QTOFsplash10-0zgi-4001930000-a7b82244d5b24f9d82722017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 20V, Positive-QTOFsplash10-0a6u-7092200000-aed6b52e614a380e20972017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 40V, Positive-QTOFsplash10-0cdi-8096100000-9e0fc4111fc6116e0ea32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 10V, Negative-QTOFsplash10-01ox-9000100000-17674b637937da23d27e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 20V, Negative-QTOFsplash10-03kc-9000200000-0c5158a7b783716294852017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 40V, Negative-QTOFsplash10-08i0-9003100000-9fa5be631de6c09946db2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 10V, Positive-QTOFsplash10-0uei-0009860000-3f8f57d106338053ebf92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 20V, Positive-QTOFsplash10-08i9-1009800000-aee94ac4fa03a5892a8b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 40V, Positive-QTOFsplash10-01pc-9447100000-e80928204b8b61c380562021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 10V, Negative-QTOFsplash10-00di-9000400000-1b0cb5667fe2a113acc92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 20V, Negative-QTOFsplash10-03dl-9001000000-ec0113eb53d740f47bfc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluticasone propionate 40V, Negative-QTOFsplash10-0ab9-9000000000-5ee0549770ddf526182a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedTaking drug identified by DrugBank entry DB00588 details
UrineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedTaking drug identified by DrugBank entry DB00588 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00588
Phenol Explorer Compound IDNot Available
FooDB IDFDB023603
KNApSAcK IDNot Available
Chemspider ID392059
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluticasone_Propionate
METLIN IDNot Available
PubChem Compound444036
PDB IDNot Available
ChEBI ID31441
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBarkalow, Jufang; Chamberlin, Steven A.; Cooper, Arthur J.; Hossain, Azad; Hufnagel, John J.; Langrid Method for the preparation of fluticasone and related 17b-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods. 2001, Patent CA2400919A1 (https://patents.google.com/patent/CA2400919A1/en17)
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dao Nguyen X, Robinson DS: Fluticasone propionate increases CD4CD25 T regulatory cell suppression of allergen-stimulated CD4CD25 T cells by an IL-10-dependent mechanism. J Allergy Clin Immunol. 2004 Aug;114(2):296-301. [PubMed:15316506 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
References
  1. Sano A, Munoz NM, Sano H, Choi J, Zhu X, Jacobs B, Leff AR: Inhibition of cPLA2 translocation and leukotriene C4 secretion by fluticasone propionate in exogenously activated human eosinophils. Am J Respir Crit Care Med. 1999 Jun;159(6):1903-9. [PubMed:10351938 ]
  2. Myo S, Zhu X, Myou S, Meliton AY, Liu J, Boetticher E, Lambertino AT, Xu C, Munoz NM, Leff AR: Additive blockade of beta 2-integrin adhesion of eosinophils by salmeterol and fluticasone propionate. Eur Respir J. 2004 Apr;23(4):511-7. [PubMed:15083746 ]
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. Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [PubMed:16565171 ]
  2. Murai T, Reilly CA, Ward RM, Yost GS: The inhaled glucocorticoid fluticasone propionate efficiently inactivates cytochrome P450 3A5, a predominant lung P450 enzyme. Chem Res Toxicol. 2010 Aug 16;23(8):1356-64. doi: 10.1021/tx100124k. [PubMed:20707410 ]
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [PubMed:16565171 ]
  2. Murai T, Reilly CA, Ward RM, Yost GS: The inhaled glucocorticoid fluticasone propionate efficiently inactivates cytochrome P450 3A5, a predominant lung P450 enzyme. Chem Res Toxicol. 2010 Aug 16;23(8):1356-64. doi: 10.1021/tx100124k. [PubMed:20707410 ]
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
References
  1. Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [PubMed:16565171 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:
PGR
Uniprot ID:
P06401
Molecular weight:
98980.0
References
  1. Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. [PubMed:16507850 ]
  2. Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ: Mometasone furoate is a less specific glucocorticoid than fluticasone propionate. Eur Respir J. 2002 Dec;20(6):1386-92. [PubMed:12503693 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Gene Name:
NR3C2
Uniprot ID:
P08235
Molecular weight:
107066.6
References
  1. Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ: Mometasone furoate is a less specific glucocorticoid than fluticasone propionate. Eur Respir J. 2002 Dec;20(6):1386-92. [PubMed:12503693 ]
  2. Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. [PubMed:16507850 ]