CAS 80474-14-2|Flovent HFA|fluticasone propionate|Flunase|Flonase|Cutivate|Flixotide|Fluticasone Propionate|fluticasone propionate|(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)...

General Information

Structure

Molecular Formula

C₂₅H₃₁F₃O₅S

Molecular Mass

500.5708496

Exact Mass

500.18442975

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

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

Polarizability

47.31395

Polar Surface Area

80.67

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

3.69

LOG S

-4.64

Solubility (Water)

1.14e-02 g/l

Data Source

Names and Identifiers

Brand Name

Flovent HFAFlunaseFlonaseCutivateFlixotideFlovent Diskus 100Flovent Diskus 50FloventAdvair DiskusAdvair Diskus 500/50FlixonaseAdvair Diskus 250/50Advair Diskus 100/50Flovent Diskus 250

IUPAC Traditional name

fluticasone propionate

Synonyms

Fluticasone Propionatefluticasone propionateVeramystFlonaseFloventCCI 18781Flutivate(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) esterFlutideZoflufCutivateAtemur MiteFlixonaseFlutide NFluticasone propionate

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 (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

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

PubChem SID

MDL Number

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

-20°C Freezer

RTECS

BV7980000

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

German water hazard class

MSDS Link

Download link

Product Information

Salt Data

propionate

Empirical Formula (Hill Notation)

C25H31F3O5S

Purity

≥98% (HPLC)

97%

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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

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.

TRC

F599500

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

Flovent HFAFlunaseFlonaseCutivateFlixotideFlovent Diskus 100Flovent Diskus 50FloventAdvair DiskusAdvair Diskus 500/50FlixonaseAdvair Diskus 250/50Advair Diskus 100/50Flovent Diskus 250

IUPAC Traditional name

fluticasone propionate

Synonyms

IUPAC name

Registration numbers

CAS Number

PubChem CID

PubChem SID

MDL Number

Properties

Safety Information

Storage Condition

-20°C

-20°C Freezer

RTECS

BV7980000

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

German water hazard class

MSDS Link

Download link

Product Information

Salt Data

propionate

Empirical Formula (Hill Notation)

C25H31F3O5S

Purity

≥98% (HPLC)

97%

Certificate of Analysis

Download link

Molecule Details

DrugBank

DB00588

Drug Groups

approved; investigational

Description

Indication

For the maintenance treatment of asthma as prophylactic therapy and for patients requiring oral corticosteroid therapy for asthma.

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

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