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

• ChemBase ID: 178874
• Molecular Formular: C24H31FO6
• Molecular Mass: 437.47570771
• Monoisotopic Mass: 437.22053145
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)(C1([C@@H](C2)O[13C](O1)([13CH3])[13CH3])C(=O)CO)C)F)C
• Canonical SMILES: OCC(=O)C12O[13C](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)([13CH3])[13CH3]
• 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/i1+1,2+1,20+1
• InChIKey: YNDXUCZADRHECN-YIBYAAHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6-bis(^1^3C)methyl-9,13-dimethyl(6-^1^3C)-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-bis(^1^3C)methyl-9,13-dimethyl(6-^1^3C)-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-13C3; Adcortyl-13C3; Azmacort-13C3; Delphicort-13C3; Extracort-13C3; Ftorocort-13C3; Kenacort-A-13C3; Tramacin-13C3; Triam-13C3; Triamcinolone-13C3 Acetonide

Database IDs

• PubChem SID: 164234784
• PubChem CID: 71752671

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 to Off-White Solid
• Melting Point: 164-166°C (dec.)

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - T767167

A labelled 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)