(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-[2-hydroxy(2H2)acetyl]-2,15-dimethyl(6,8,8-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 178872
• Molecular Formular: C21H27FO6
• Molecular Mass: 394.4338832
• Monoisotopic Mass: 394.1791668
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@@]2(C(=O)CO)O)O)C)O)F)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](O)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C21H27FO6/c1-18-6-5-12(24)7-11(18)3-4-13-14-8-15(25)21(28,17(27)10-23)19(14,2)9-16(26)20(13,18)22/h5-7,13-16,23,25-26,28H,3-4,8-10H2,1-2H3/t13-,14-,15+,16-,18-,19-,20-,21-/m0/s1
• InChIKey: GFNANZIMVAIWHM-OBYCQNJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione-d5; 9α-Fluoro-16α-Hydroxyprednisolone-d5; Adcortyl-d5; Aristocort-d5; CL 19823-d5; Triamcinlon-d5; Triamcinolon-d5; Tricortale-d5; Volon-d5; Triamcinolone-d5DISCONTINUED

Database IDs

• PubChem SID: 164234782
• PubChem CID: 71752670

CALCULATED PROPERTIES

• Acid pKa: 11.751343
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.241693
• LogD (pH = 7.4): 0.24167393
• Log P: 0.24169324
• Molar Refractivity: 99.3828 cm^3
• Polarizability: 38.45974 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T767162

Labelled Triamcinolone. Triamcinolone is a glucocorticoid. Triamcinolone is used as an antiasthmatic (inhalant); antiallergic (nasal).

REFERENCES

• Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972)
• Bernstein, I.L., et al.: Chest, 81, 20 (1972)