(1S,2S,4R,8S,9S,11S,12R,13S,19R)-12-fluoro-11,19-dihydroxy-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: 171395
• Molecular Formular: C24H31FO7
• Molecular Mass: 450.4971432
• Monoisotopic Mass: 450.20538155
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](C[C@H]2O)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(O1)(C)C)C(=O)CO)C)F)C
• Canonical SMILES: OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1C[C@H](C1=CC(=O)C=C[C@]21C)O)F)(C)C
• InChI: InChI=1S/C24H31FO7/c1-20(2)31-19-9-13-14-8-16(28)15-7-12(27)5-6-21(15,3)23(14,25)17(29)10-22(13,4)24(19,32-20)18(30)11-26/h5-7,13-14,16-17,19,26,28-29H,8-11H2,1-4H3/t13-,14-,16+,17-,19+,21-,22-,23-,24+/m0/s1
• InChIKey: WMJSKWRCHLTCCW-PXGYRYRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12R,13S,19R)-12-fluoro-11,19-dihydroxy-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,8S,9S,11S,12R,13S,19R)-12-fluoro-11,19-dihydroxy-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: (6β,11β,16α)-9-Fluoro-6,11,21-trihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; 6β-Hydroxy Triamcinolone Acetonide

Database IDs

• CAS Number: 3869-32-7
• PubChem SID: 164227305
• PubChem CID: 29982180

CALCULATED PROPERTIES

• Acid pKa: 13.37027
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.7133068
• LogD (pH = 7.4): 0.7133063
• Log P: 0.7133068
• Molar Refractivity: 113.1053 cm^3
• Polarizability: 44.037464 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Pyridine
• Apperance: White to Off-White Solid
• Melting Point: 269-272°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H970050

The major metabolite of Triamcinolone acetonide.

REFERENCES

• Edsbacker, S., et al.: Drug Metab. Dispos., 11, 590 (1983)
• Szefler, S., et al.: Eur. J. Clin. Pharmacol., 30, 323 (1983)
• Hansel, T., et al.: J. Immunol. Methods, 145, 105 (1983)
• Argenti, D., et al.: J. Clin. Pharmacol., 39, 695 (1983)