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S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate

Fluticasone propionate

CAS: 80474-14-2

Molecular Formula: C25H31F3O5S

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S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate - Names and Identifiers

Name Fluticasone propionate
Synonyms flutide
cci18781
-17-(1-oxopropoxy)-,s-(fluoromethyl)ester,(6-alpha,11-beta,16-alpha,17-alph
androsta-1,4-diene-17-carbothioicacid,6,9-difluoro-11-hydroxy-16-methyl-3-oxo
S-(fluoromethyl) (6alpha,11beta,16alpha,17alpha)-6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carbothioate
(6A,11B,16A,17A)-6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID FLUOROMETHYL ESTER
S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate
s-fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate
(6a,11b,16a,17a)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic acid S-(fluoromethyl) ester
(6alpha,11beta,16alpha,17alpha)-6,9-difluoro-17-{[(fluoromethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-yl propanoate
(6alpha,8xi,11beta,16alpha,17alpha)-6,9-difluoro-17-{[(fluoromethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-yl propanoate
(6 ALPHA,11 BETA,16 ALPHA,17 ALPHA)-6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID FLUOROMETHYL ESTER
CAS 80474-14-2
EINECS 617-082-4
InChI InChI=1/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 WMWTYOKRWGGJOA-CENSZEJFSA-N

S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate - Physico-chemical Properties

Molecular FormulaC25H31F3O5S
Molar Mass500.57
Density1.32±0.1 g/cm3(Predicted)
Melting Point275 °C
Boling Point568.3±50.0 °C(Predicted)
Specific Rotation(α)D +30° (c = 0.35)
Flash Point288.4°C
Solubility DMSO 100 mg/mL ;Water <1 mg/mL; Ethanol 5 mg/mL
Vapor Presure1.52E-14mmHg at 25°C
AppearanceWhite Solid
Colorwhite
Merck14,4211
pKa12.53±0.70(Predicted)
Storage ConditionStore at RT
Refractive Index31 ° (C=1, Dioxane)
MDLMFCD00866007
Physical and Chemical PropertiesCrystalline, melting point 272-273 °c (decomposition). ^[α]D 30 °(C = 0.35).
In vitro studyIn human lung fibroblasts, Fluticasone propionate(1 pM) inhibited the constitutive and TGF-β-induced expression of α-SMA. Fluticasone propionate blocks nuclear translocation of the pro-inflammatory transcription factor NF-κB induced by TNF-α in human lung fibroblasts. Fluticasone propionate inhibits IL-13 (tyrosine kinase 2,STAT1,STAT3,STAT6, mitogen-activated protein kinase)-induced activation of the Janus kinase/STAT pathway in the early stages of lung fibroblast differentiation. In mildly or fully differentiated myofibroblast cultures, Fluticasone propionate still exhibited potential anti-inflammatory activity, although it only inhibited phosphorylation of tyrosine kinase 2. In early and mildly differentiated myofibroblasts, Fluticasone propionate inhibited constitutive and TGF-β-induced expression of α-smooth muscle actin, which is a major marker of myofibroblast differentiation. Fluticasone propionate exhibited an additional powerful anti-inflammatory effect, reducing the nuclear translocation of myofibroblast NF-κB independent of its degree of differentiation. Fluticasone propionate inhibited allergen-induced T cell proliferation, expression of IL-3,IL-5, and GM-CSF mRNA, and secretion of the corresponding proteins in a concentration-dependent manner. Fluticasone propionate significantly inhibited allergen-induced T-cell production of asthma-related cytokines.
In vivo studyIn horses, Fluticasone propionate administration after induction of severe eye deterioration resulted in complete resolution of clinical symptoms, normalization of pulmonary function tests and a significant decrease in bronchoalveolar neutrophil lavage (BAL).

S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate - Risk and Safety

Safety DescriptionS22 - Do not breathe dust.
S24/25 - Avoid contact with skin and eyes.
WGK Germany2
RTECSBV7980000
HS Code29372900
ToxicityLD50 oral in rat: > 2gm/kg
S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate
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View History
S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate
2-METHYLACETOPHENONE
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4-Benzyloxy-3-chlorobroMobenzene
Glycolic acid, di-TMS
Alkaloid A, fromCoptis groenlandica
tert-Butyl 4-aminobenzoate
聚肌苷酸
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