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

• ChemBase ID: 159411
• Molecular Formular: C26H33FO7
• Molecular Mass: 476.5344232
• Monoisotopic Mass: 476.22103162
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]1[C@]2(OC(O1)(C)C)C(=O)COC(=O)C)C)O)F)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]12OC(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)C
• InChI: InChI=1S/C26H33FO7/c1-14(28)32-13-20(31)26-21(33-22(2,3)34-26)11-18-17-7-6-15-10-16(29)8-9-23(15,4)25(17,27)19(30)12-24(18,26)5/h8-10,17-19,21,30H,6-7,11-13H2,1-5H3/t17-,18-,19-,21+,23-,24-,25-,26+/m0/s1
• InChIKey: VOBDXTSTTMAKHK-VHDCPBDGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
• Synonyms: (11β,16α)-21-(Acetyloxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; Triamcinolone Acetonide 21-Acetate; 21-(Acetyloxy) Triamcinolone Acetonide

Database IDs

• CAS Number: 3870-07-3
• PubChem SID: 162253546
• PubChem CID: 15482000

CALCULATED PROPERTIES

• Acid pKa: 13.633902
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.3852432
• LogD (pH = 7.4): 2.385243
• Log P: 2.3852432
• Molar Refractivity: 120.7413 cm^3
• Polarizability: 47.220886 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-White Solid
• Melting Point: 262-265°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A187420

Derivative of Triamcinolone Acetonide, a glucocorticoid, 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)