ChemFOnt: Showing chemical card for Fluticasone propionate (CFc000002377)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:15 UTC

Chemfont ID

CFc000002377

Molecule Identification

Common Name

Fluticasone propionate

Definition

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. 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cutivate	ChEBI
Flonase	Kegg
Flovent	Kegg
Cutivic acid	Generator
Fluticasone propionic acid	Generator
Flovent diskus 250	HMDB
Flovent diskus 50	HMDB
CCI-18781cutivATE	HMDB
Flovent diskus 100	HMDB
Flovent hfa	HMDB
FLUTICASONE	HMDB
CCI 18781	HMDB
CCI-18781cutivic acid	HMDB
Asmatil	HMDB
Axotide	HMDB
Brethal	HMDB
Cultivate	HMDB
Flixonase	HMDB
Flixonase nasal spray	HMDB
Flixotide	HMDB
Flixotide disk	HMDB
Flixotide disks	HMDB
Flixotide inhaler	HMDB
Flovent diskus	HMDB
Flovent rotadisk	HMDB
Fluinol	HMDB
Flunase	HMDB
Flusonal	HMDB
Fluspiral	HMDB
Fluticasonpropionat allen	HMDB
Flutide	HMDB
Flutivate	HMDB
HFA, flovent	HMDB
Propionate, fluticasone	HMDB

Chemical Formula

C₂₅H₃₁F₃O₅S

Average Molecular Weight

500.571

Monoisotopic Molecular Weight

500.184429407

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 Number

80474-14-2

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 Key

WMWTYOKRWGGJOA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

thioester (CHEBI:31441 )
propanoate ester (CHEBI:31441 )
11beta-hydroxy steroid (CHEBI:31441 )
steroid ester (CHEBI:31441 )
fluorinated steroid (CHEBI:31441 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:31441 )
corticosteroid (CHEBI:31441 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0005036)
Membrane (HMDB: HMDB0005036)

Source

Exogenous

Exogenous (HMDB: HMDB0005036)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0005036)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.69	ALOGPS
logP	3.72	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.56	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.65 m³·mol⁻¹	ChemAxon
Polarizability	49.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0005036

DrugBank ID

DB00588

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023603

KNApSAcK ID

Not Available

Chemspider ID

392059

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluticasone_Propionate

METLIN ID

Not Available

PubChem Compound

444036

PDB ID

Not Available

ChEBI ID

31441

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Barkalow, 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)

Showing chemical card for Fluticasone propionate (CFc000002377)

MOL for CFc000002377 (Fluticasone propionate)

3D MOL for CFc000002377 (Fluticasone propionate)

3D SDF for CFc000002377 (Fluticasone propionate)

3D-SDF for CFc000002377 (Fluticasone propionate)

PDB for CFc000002377 (Fluticasone propionate)

3D PDB for CFc000002377 (Fluticasone propionate)

SMILES for CFc000002377 (Fluticasone propionate)

INCHI for CFc000002377 (Fluticasone propionate)

Structure for CFc000002377 (Fluticasone propionate)

3D Structure for CFc000002377 (Fluticasone propionate)