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Fluticasone

CAT: 0804-HY-B0603-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0603-01Size:1 mg
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Description
Fluticasone is an inhaled corticosteroid used for respiratory research. Fluticasone is a Smo agonist with an IC50 value of 99 nM. Fluticasone activates Hedgehog signaling and promotes the proliferation of primary neuronal stem or precursor cells[1][2].
CAS Number
90566-53-3
UNSPSC
12352100
Hazard Statement
H315, H319, H320
Target
Glucocorticoid Receptor; Smo
Type
Reference compound
Related Pathways
Immunology/Inflammation; Stem Cell/Wnt; Vitamin D Related/Nuclear Receptor
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Infection; Endocrinology; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/fluticasone.html
Concentration
10mM
Purity
98.70
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
C[C@]([C@](O)1C(SCF)=O)(C[C@@H]2O)[C@](C[C@H]1C)([H])[C@@](C[C@@H]3F)([H])[C@]2([C@](C3=CC4=O)(C=C4)C)F
Molecular Formula
C22H27F3O4S
Molecular Weight
444.51
Precautions
H315, H319, H320
References & Citations
[1]Seidel P, et al. Thiazolidinediones inhibit airway smooth muscle release of the chemokine CXCL10: in vitro comparison with current asthma therapies. Respir Res. 2012 Oct 4. 13 (1) :90.|[2]Wang J, et al. Identification of select glucocorticoids as Smoothened agonists: potential utility for regenerative medicine. Proc Natl Acad Sci U S A. 2010 May 18. 107 (20) :9323-8. |[3]Ying Wang, et al. Tiotropium and Fluticasone Inhibit Rhinovirus-Induced Mucin Production via Multiple Mechanisms in Differentiated Airway Epithelial Cells. Front. Cell. Infect. Microbiol., 2020 Jun. |[4]Singanayagam A, et al. Effect of fluticasone propionate on virus-induced airways inflammation and anti-viral immune responses in mice. Lancet. 2015 Feb 26. 385 (Suppl 1) :S88.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Fluticasone

Fluticasone is a trifluorinated corticosteroid used in the form of its propionate ester for treatment of allergic rhinitis. It has a role as an anti-asthmatic drug and an anti-allergic agent. It is a 17alpha-hydroxy steroid, an 11beta-hydroxy steroid, a 3-oxo-Delta(4) steroid, a fluorinated steroid, a corticosteroid and a thioester. It derives from a hydride of an androstane.

CAS Number90566-53-3
PubChem CID5311101
IUPAC NameS-(fluoromethyl) (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate
Molecular FormulaC22H27F3O4S
Molecular Weight444.5
XLogP3.2
Topological Polar Surface Area99.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Heavy Atom Count30
Formal Charge0
Complexity861
SMILES
C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)SCF)O)C)O)F)C)F
InChI
InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
InChIKey
MGNNYOODZCAHBA-GQKYHHCASA-N
Chemical Structure
2D Structure
2D structure of Fluticasone
CAS: 90566-53-3
CID: 5311101
Formula: C22H27F3O4S
MW: 444.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight444.5
XLogP33.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Exact Mass444.15821500
Monoisotopic Mass444.15821500
Topological Polar Surface Area99.9 Ų
Heavy Atom Count30
Formal Charge0
Complexity861
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
TRC-F599456-5MGFluticasone
C8710-200Fluticasone Furoate
B2096-50Fluticasone propionate
CS-T-103423Fluticasone-d3
sc-489892Fluticasone Acetate

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