(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: 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

NAMES AND DATABASE IDS

Names

• 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,^7.0^1^1,^1^5]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

Database IDs

• CAS Number: 80474-14-2
• MDL Number: MFCD00866007
• PubChem SID: 46506140; 160963933
• PubChem CID: 444036

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.557201
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7180047
• LogD (pH = 7.4): 3.7180042
• Log P: 3.7180047
• Molar Refractivity: 121.6503 cm^3
• Polarizability: 47.31395 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.69
• LOG S: -4.64
• Solubility (Water): 1.14e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.51 mg/L (insoluble); Chloroform; DMF; DMSO; DMSO: ≥10 mg/mL
• Apperance: white powder; White Solid
• Melting Point: 272-273°C dec.
• Hydrophobicity(logP): 3.4

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: BV7980000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC); 97%
• Salt Data: propionate
• Empirical Formula (Hill Notation): C25H31F3O5S

DETAILS

DrugBank - DB00588

• 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

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

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

A derivative of Flumethasone. An antiallergic; anti-asthmatic; anti-inflammatory.

REFERENCES

• 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)