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80474-14-2 molecular structure
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(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl propanoate

ChemBase ID: 470
Molecular Formular: C25H31F3O5S
Molecular Mass: 500.5708496
Monoisotopic Mass: 500.18442975
SMILES and InChIs

SMILES:
S(C(=O)[C@]1(OC(=O)CC)[C@@]2([C@H]([C@H]3[C@](F)([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)[C@@H](F)C3)C)C[C@H]1C)C)CF
Canonical SMILES:
FCSC(=O)[C@@]1(OC(=O)CC)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F
InChI:
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
InChIKey:
WMWTYOKRWGGJOA-CENSZEJFSA-N

Cite this record

CBID:470 http://www.chembase.cn/molecule-470.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl propanoate
(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
IUPAC Traditional name
fluticasone propionate
Brand Name
Advair Diskus 100/50
Advair Diskus 250/50
Advair Diskus 500/50
Cutivate
Flixonase
Flixotide
Flonase
Flovent
Flovent Diskus 100
Flovent Diskus 250
Flovent Diskus 50
Flovent HFA
Flunase
Advair Diskus
Synonyms
(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
Fluticasone propionate
fluticasone propionate
Fluticasone Propionate
Flonase
Veramyst
Atemur Mite
CCI 18781
Cutivate
Flixonase
Flovent
Flutide
Flutide N
Flutivate
Zofluf
CAS Number
80474-14-2
MDL Number
MFCD00866007
PubChem SID
46506140
160963933
PubChem CID
444036

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.557201  H Acceptors
H Donor LogD (pH = 5.5) 3.7180047 
LogD (pH = 7.4) 3.7180042  Log P 3.7180047 
Molar Refractivity 121.6503 cm3 Polarizability 47.31395 Å3
Polar Surface Area 80.67 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 3.69  LOG S -4.64 
Solubility (Water) 1.14e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.51 mg/L (insoluble) expand Show data source
Chloroform expand Show data source
DMF expand Show data source
DMSO expand Show data source
DMSO: ≥10 mg/mL expand Show data source
Apperance
white powder expand Show data source
White Solid expand Show data source
Melting Point
272-273°C dec. expand Show data source
Hydrophobicity(logP)
3.4 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
BV7980000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98% (HPLC) expand Show data source
97% expand Show data source
Salt Data
propionate expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C25H31F3O5S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00588 external link
Item Information
Drug Groups approved; investigational
Description Fluticasone 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.
Indication For the maintenance treatment of asthma as prophylactic therapy and for patients requiring oral corticosteroid therapy for asthma.
Pharmacology Fluticasone 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.
Affected Organisms
Humans and other mammals
Biotransformation Fluticasone propionate is metabolized in the liver by cytochrome P450 3A4-mediated hydrolysis of the 5-fluoromethyl carbothioate grouping. This transformation occurs in 1 metabolic step to produce the inactive 17-(beta)-carboxylic acid metabolite, the only known metabolite detected in man.
Absorption The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier.
Half Life 10 hours
Protein Binding 91%
Distribution * 2.3 to 16.7 L/kg
Clearance * 1093 mL/min
External Links
RxList
Drugs.com
Selleck Chemicals - S1992 external link
Research Area: Immunology
Biological Activity:
Fluticasone propionate (Flonase, Veramyst) is a synthetic corticosteroid which is derived from fluticasone used to treat asthma and allergic rhinitis (hay fever). Fluticasone propionate (Flonase, Veramyst) is also used to treat eosinophilic esophagitis. In addition, fluticasone propionate is also available as a cream for the treatment of eczema and psoriasis. [1]References on Fluticasone propionate (Flonase, Veramyst)[1] http://en.wikipedia.org/wiki/Fluticasone_propionate, ,
Sigma Aldrich - F9428 external link
Biochem/physiol Actions
Fluticasone propionate is a second generation glucocorticoid. Used as an anti-inflammatory agent for asthma. Shown to enhance eosinophil apoptosis in a concentration-dependent manner via the glucocorticoid receptor.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F9428.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - F599500 external link
A derivative of Flumethasone. An antiallergic; anti-asthmatic; anti-inflammatory.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Fluticasone_propionate
  • • Meltzer, E.O., et al.: J. Allergy Clin. Immunol., 86, 221 (1990)
  • • Mitchison, H.C., et al.: Gut, 32, 260 (1990)
  • • Phillipps, G.H., et al.: J. Med. Chem., 37, 3717 (1994)
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PATENTS

PATENTS

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INTERNET

INTERNET

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