(1R,2S,8S,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

• ChemBase ID: 179695
• Molecular Formular: C25H31F3O5S
• Molecular Mass: 500.5708496
• Monoisotopic Mass: 500.18442975
• SMILES: [C@]12([C@@]3(C(C4[C@@]([C@]([C@@H](C4)C)(C(=O)SCF)OC(=O)CC)(C[C@@H]3O)C)C[C@@H](C1=CC(=O)C=C2)F)F)C
• Canonical SMILES: FCSC(=O)[C@@]1(OC(=O)CC)[C@H](C)CC2[C@]1(C)C[C@H](O)[C@]1(C2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F
• 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-WYZONABHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• IUPAC Traditional name: (1R,2S,8S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• Synonyms: Fluticasone Propionate

Database IDs

• CAS Number: 80474-14-2
• PubChem SID: 164235605
• PubChem CID: 9811617

CALCULATED PROPERTIES

• Acid pKa: 13.557201
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7180047
• LogD (pH = 7.4): 3.7180042
• Log P: 3.7180047
• Molar Refractivity: 121.6503 cm^3
• Polarizability: 47.31395 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibitor of multiple cell types (e.g., mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils) and; mediate production or secretion (e.g., histamine, eicosanoids, leukotrienes, and cytokines)

Product Information

• Application(s): Antiinflammatory agent; Corticosteroid; Used for treatment of inflammatory bowel disease, asthma and allergic rhinitis

REFERENCES

• U.S. Pat., 1982, Synthelabo, 4 315 007; CA, 96, 162737e, (synth)
• Allen, J., J. Labelled Compd. Radiopharm., 1983, 20, 1283, (synth)
• Scott, M.G. et al., Eur. J. Clin. Pharmacol., 1989, 37, 53, (pharmacokinet)
• Rouchouse, A. et al., J. Chromatogr., 1990, 506, 601, (hplc, enantiomers)
• Lefevre-Borg, F. et al., Br. J. Pharmacol., 1993, 109, 1282, (pharmacol)
• Wilde, M.I. et al., Drugs, 1993, 45, 410, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 342