ChemSpider 2D Image | Fluticasone propionate | C25H31F3O5S

Fluticasone propionate

  • Molecular FormulaC25H31F3O5S
  • Average mass500.571 Da
  • Monoisotopic mass500.184418 Da
  • ChemSpider ID392059

  • defined stereocentres - 9 of 9 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(6a,11b,16a,17a)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic Acid S-(Fluoromethyl) Ester
(6α,11β,16α,17α)-6,9-Difluor-17-{[(fluormethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-ylpropionat [German] [ACD/IUPAC Name]
(6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic acid S-(fluoromethyl) ester
(6α,11β,16α,17α)-6,9-difluoro-17-{[(fluoromethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-yl propanoate
(6α,11β,16α,17α)-6,9-Difluoro-17-{[(fluoromethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-yl propionate [ACD/IUPAC Name]
80474-14-2 [RN]
90566-53-3 [RN]
948566-12-9 [RN]
Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S-(fluoromethyl) ester, (6α,11β,16α,17α)- [ACD/Index Name]
BV7980000
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:31441 [DBID]
CCI-18781 [DBID]
D01708 [DBID]
FN-25 [DBID]
Prestwick0_000997 [DBID]
Prestwick1_000997 [DBID]
SPBio_002984 [DBID]
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      Sold for research purposes under agreement from GlaxoSmithKline Tocris Bioscience 2007

    • Chemical Class:

      A trifluorinated corticosteroid that consists of 6alpha,9-difluoro-11beta,17alpha-dihydroxy-17beta-{[(fluoromethyl)sulfanyl]carbonyl}-16-methyl-3-oxoandrosta-1,4-diene bearing a propionyl substituent at position 17; has anti-inflammatory, anti-asthmatic and anti-allergic activity. ChEBI CHEBI:31441
      A trifluorinated corticosteroid that consits of 6<stereo>alpha</stereo>,9-difluoro-11<stereo>beta</stereo>,17<stereo>alpha</stereo>-dihydroxy-17<stereo>beta</stereo>-{[(fluoromethyl)sulfanyl]carbonyl} -16-methyl-3-oxoandrosta-1,4-diene bearing a propionyl substituent at position 17; has anti-inflammatory, anti-asthmatic and anti-allergic activity. ChEBI CHEBI:31441
      A trifluorinated corticosteroid that consits of 6alpha,9-difluoro-11beta,17alpha-dihydroxy-17beta-{[(fluoromethyl)sulfanyl]carbonyl}; -16-methyl-3-oxoandrosta-1,4-diene bearing a propionyl substituent at position 17; has anti-inflammatory, anti-asthmatic and anti-allergic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31441

    • Bio Activity:

      Biochemicals & small molecules/Agonists & activators Hello Bio [HB1091]
      Fluticasone propionate is a high affinity, selective GR (glucocorticoid receptor) agonist which is derived from fluticasone used to treat asthma and allergic rhinitis. MedChem Express
      Fluticasone propionate is a high affinity, selective GR (glucocorticoid receptor) agonist which is derived from fluticasone used to treat asthma and allergic rhinitis.; Target: Glucocorticoid Receptor ; Fluticasone propionate is a corticosteroid derived from fluticasone used to treat asthma and allergic rhinitis. MedChem Express HY-B0154
      Fluticasone propionate is a high affinity, selective GR (glucocorticoid receptor) agonist which is derived from fluticasone used to treat asthma and allergic rhinitis.;Target: Glucocorticoid ReceptorFluticasone propionate is a corticosteroid derived from fluticasone used to treat asthma and allergic rhinitis. It is also used to treat eosinophilic esophagitis. Fluticasone propionate is a synthetic trifluorinated glucocorticoid. It is highly lipophilic (logp octanol/water 3.69). In studies the topical drug has been associated with burning, stinging, skin irritation, blisters, dryness, skin infection, infected eczema, viral warts,impetigo, atopic dermatitis, pruritus, exacerbation of pruritus, exacerbation of eczema, erythema, and folliculitis.;There are also numerous side effects associated with the oral version of this medication including headache, stuffy or runny nose, difficulty speaking, sore or irritated throat and painful white patches in the mouth or throat. Candidiasis of m MedChem Express HY-B0154
      Glucocorticoid Receptor Tocris Bioscience 2007
      Glucocorticoid Receptor MedChem Express HY-B0154
      GPCR/G protein MedChem Express HY-B0154
      GPCR/G protein; MedChem Express HY-B0154
      High affinity, selective glucocorticoid receptor agonist (Kd = 0.5 nM). Potently stimulates glucocorticoid receptor-mediated transactivation of gene expression and enhances human eosinophil apoptosis (EC50 = 3.7 nM) in vitro. Inhibits mast cell accumulation in nasal mucosa following topical administration. Lipophilic anti-inflammatory agent with low oral bioavailability. Also potentiates KV1 chann els (EC50 = 37 nM). Tocris Bioscience 2007
      High affinity, selective glucocorticoid receptor agonist (Kd = 0.5 nM). Potently stimulates glucocorticoid receptor-mediated transactivation of gene expression and enhances human eosinophil apoptosis (EC50 = 3.7 nM) in vitro. Inhibits mast cell accumulation in nasal mucosa following topical administration. Lipophilic anti-inflammatory agent with low oral bioavailability. Also potentiates KV1 channels (EC50 = 37 nM). Tocris Bioscience 2007
      Nuclear Receptors Tocris Bioscience 2007
      Receptors & Transporters/Nuclear hormone Hello Bio [HB1091]
      Selective glucocorticoid receptor agonist Hello Bio [HB1091]
      Selective glucocorticoid receptor agonist (K<sub>d</sub> = 0.5 nM). Reduces expression of mast cells, suppresses mast cell degranulation, enhances eosinophil apoptosis and inhibits T cell proliferation. Potentiates K<sub>v</sub>1 channel current (EC<sub>50</sub> = 37 nM). Shows anti-inflammatory and anti-allergy actions. Hello Bio [HB1091]
      Selective high affinity glucocorticoid receptor agonist Tocris Bioscience 2007

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 568.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.5 mmHg at 25°C
Enthalpy of Vaporization: 98.0±6.0 kJ/mol
Flash Point: 297.5±30.1 °C
Index of Refraction: 1.556
Molar Refractivity: 121.1±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 3.73
ACD/LogD (pH 5.5): 3.71
ACD/BCF (pH 5.5): 391.28
ACD/KOC (pH 5.5): 2496.35
ACD/LogD (pH 7.4): 3.71
ACD/BCF (pH 7.4): 391.27
ACD/KOC (pH 7.4): 2496.33
Polar Surface Area: 106 Å2
Polarizability: 48.0±0.5 10-24cm3
Surface Tension: 48.1±5.0 dyne/cm
Molar Volume: 377.0±5.0 cm3

Click to predict properties on the Chemicalize site


Advertisement