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

• ChemBase ID: 178873
• Molecular Formular: C24H31FO6
• Molecular Mass: 434.4977432
• Monoisotopic Mass: 434.21046693
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]1C2(OC(O1)(C)C)C(=O)CO)C)O)F)C
• Canonical SMILES: OCC(=O)C12OC(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/C24H31FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h7-9,15-17,19,26,28H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24?/m0/s1
• InChIKey: YNDXUCZADRHECN-JZKLOLMGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• IUPAC Traditional name: (1S,2S,4R,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• Synonyms: (11β,16α)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; Adcortyl; Azmacort; Delphicort; Extracort; Ftorocort; Kenacort-A; Tramacin; Triam; Tricinolon; Vetalog; Volon A; Triamcinolone Acetonide

Database IDs

• CAS Number: 76-25-5
• PubChem SID: 164234783
• PubChem CID: 9845781

CALCULATED PROPERTIES

• Acid pKa: 13.401961
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.9441179
• LogD (pH = 7.4): 1.9441174
• Log P: 1.9441179
• Molar Refractivity: 111.5898 cm^3
• Polarizability: 43.3673 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: >280°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T767165

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)