[(6S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate

Base Information

• Chemical Name: [(6S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
• CAS No.: 80474-14-2
• Molecular Formula: C25H31F3O5S
• Molecular Weight: 500.579
• Hs Code.: 29372900
• European Community (EC) Number: 617-082-4
• Wikipedia: Fluticasone_propionate
• Mol file: 80474-14-2.mol

Synonyms:80474-14-2;[(6S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate;[(6S,9R,10S,11S,13S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate;Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S-(fluoromethyl) ester, (6.alpha.,11.beta.,16.alpha.,17.alpha.)-;C25-H31-F3-O5-S;SCHEMBL416179;CHEMBL304244;WMWTYOKRWGGJOA-WYZONABHSA-N;AKOS015969667;F0525;,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester;Propionic acid (6S,9R,10S,11S,13S,16R,17R)-6,9-difluoro-17-fluoromethylsulfanylcarbonyl-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12

Chemical Property of [(6S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 1.52E-14mmHg at 25°C
• Melting Point: 275 °C
• Refractive Index: 31 ° (C=1, Dioxane)
• Boiling Point: 568.3 °C at 760 mmHg
• PKA: 12.53±0.70(Predicted)
• Flash Point: 297.5 °C
• PSA: 105.97000
• Density: 1.32 g/cm³
• LogP: 4.43000
• Storage Temp.: Store at RT
• Solubility.: DMSO: ≥10 mg/mL
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 500.18442974
• Heavy Atom Count: 34
• Complexity: 984

Purity/Quality:

99% ^*data from raw suppliers

Fluticasone propionate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OC1(C(CC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C)C(=O)SCF
• Isomeric SMILES: CCC(=O)O[C@@]1([C@@H](CC2[C@@]1(C[C@@H]([C@]3(C2C[C@@H](C4=CC(=O)C=C[C@@]43C)F)F)O)C)C)C(=O)SCF
• Recent EU Clinical Trials: A phase III, randomized, multicenter, parallel-group clinical trial for examining the therapeutic equivalence between Fluticasone propionate 100 mcg and salmeterol 50 mcg inhalation powder/Respirent Pharmaceuticals vs. ADVAIR DISKUS? 100/50 mcg inhalation powder/GSK in patients with asthma
• Description: Fluticasone propionate is a new glucocorticosteroid useful in the treatment of seasonal rhinitis and asthma. Compared to beclomethasone dipropionate, fluticasone propionate is reported to have a comparable side effect profile, but twice the activity in the treatment of asthma.
• Uses: Fluticasone Propionate is a derivative of Flumethasone, a glucocorticoid. Fluticasone Propionate has antiallergic, anti-asthmatic, and anti-inflammatory properties (1,2,3). 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 Proprionate is marketed under several different brand names such as Flonase(R). Fluticasone propionate is also available as a combination product of Azelastine Hydrochloride and Fluticasone Propionate called Dymista(TM). Dymista(TM) is indicated in patients over 12 years old for symptomatic relief of seasonal allergic rhinitis.
• Therapeutic Function: Glucocorticoid

Technology Process of [(6S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate

There total 38 articles about [(6S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.7%

bromofluoromethane (373-52-4) + 17-propionate carbothioic acid (80474-45-9) → flixotide (80474-14-2)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at -10 - 20 ℃; for 2h;

Reference yield: 83.0%

6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate (1351451-82-5) → flixotide (80474-14-2)

Guidance literature:

With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate); silver nitrate; In water; acetone; at 45 ℃; for 3h; Temperature; Solvent; Time; Inert atmosphere; Green chemistry;

DOI:10.1021/op5001226

Reference yield: 82.0%

fluoroiodomethane (373-53-5) + 17-propionate carbothioic acid (80474-45-9) → flixotide (80474-14-2)

Guidance literature:

With caesium carbonate; In acetonitrile; at 20 ℃; for 6h; chemoselective reaction;

DOI:10.1021/acs.orglett.9b04654

upstream raw materials:

fluoroiodomethane

17-propionate carbothioic acid

bromofluoromethane

S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate

Refernces

• 1、 -. "Fluticasone propionate synthesis method". Page/Page column 7-15. . Retrieved 2020/02/10.
• 2、 Kern, Jeffrey C.,Cancilla, Mark,Dooney, Deborah,Kwasnjuk, Kristen,Zhang, Rena,Beaumont, Maribel,Figueroa, Isabel,Hsieh, SuChun,Liang, Linda,Tomazela, Daniela,Zhang, Jeffrey,Brandish, Philip E.,Palmieri, Anthony,Stivers, Peter,Cheng, Mangeng,Feng, Guo,Geda, Prasanthi,Shah, Sanjiv,Beck, Andrew,Bresson, Damien,Firdos, Juhi,Gately, Dennis,Knudsen, Nick,Manibusan, Anthony,Schultz, Peter G.,Sun, Ying,Garbaccio, Robert M.. "Discovery of Pyrophosphate Diesters as Tunable, Soluble, and Bioorthogonal Linkers for Site-Specific Antibody-Drug Conjugates". . p. 1430 - 1445. Retrieved 2016/02/18.