2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,9,13-trimethyl-16-oxo-5-oxa-7-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-6,14,17-trien-8-yl]-2-oxoethyl acetate

• ChemBase ID: 169018
• Molecular Formular: C25H30FNO6
• Molecular Mass: 459.5072032
• Monoisotopic Mass: 459.20571591
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(=N1)C)C(=O)COC(=O)C)C)F)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]12N=C(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1CCC1=CC(=O)C=C[C@]21C)F)C
• InChI: InChI=1S/C25H30FNO6/c1-13-27-25(20(31)12-32-14(2)28)21(33-13)10-18-17-6-5-15-9-16(29)7-8-22(15,3)24(17,26)19(30)11-23(18,25)4/h7-9,17-19,21,30H,5-6,10-12H2,1-4H3/t17-,18-,19-,21+,22-,23-,24-,25+/m0/s1
• InChIKey: BYZCJOHDXLROEC-RBWIMXSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,9,13-trimethyl-16-oxo-5-oxa-7-azapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-6,14,17-trien-8-yl]-2-oxoethyl acetate
• IUPAC Traditional name: fluazacort
• Synonyms: (11β,16β)-21-(Acetyloxy)-9-fluoro-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione; Azacortid; L 6400; 9α-Fluoro-11β,21-dihydroxy-3,20-dioxo-1,4-pregnadieno[17α,16α-d]-2-methyloxazoline 21-Acetate; Fluazacort

Database IDs

• CAS Number: 19888-56-3
• PubChem SID: 162263150
• PubChem CID: 10072906

CALCULATED PROPERTIES

• Acid pKa: 13.632255
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8457892
• LogD (pH = 7.4): 1.8457918
• Log P: 1.845792
• Molar Refractivity: 116.6472 cm^3
• Polarizability: 45.406403 Å^3
• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F407400

A glucucorticoid with anti-inflammatory properties used in the treatment of skin diseases.

REFERENCES

• De Angelis, L.: Drugs Today, 12, 396 (1976)
• Nathansohn, G. et al.: Steroids, 13, 365 (1976)
• Lewis, J.D. et al.: Arzneim.-Forsch., 25, 1646 (1976)