2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-6,9,13-trimethyl-16-oxo(10,10,11-2H3)-5-oxa-7-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-6,14,17-trien-8-yl]-2-oxoethyl acetate

• ChemBase ID: 165568
• Molecular Formular: C25H31NO6
• Molecular Mass: 441.51674
• Monoisotopic Mass: 441.21513772
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(=N1)C)C(=O)COC(=O)C)C)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]12N=C(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1CCC1=CC(=O)C=C[C@]21C)C
• InChI: InChI=1S/C25H31NO6/c1-13-26-25(20(30)12-31-14(2)27)21(32-13)10-18-17-6-5-15-9-16(28)7-8-23(15,3)22(17)19(29)11-24(18,25)4/h7-9,17-19,21-22,29H,5-6,10-12H2,1-4H3/t17-,18-,19-,21+,22+,23-,24-,25+/m0/s1
• InChIKey: FBHSPRKOSMHSIF-GRMWVWQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-6,9,13-trimethyl-16-oxo(10,10,11-^2H₃)-5-oxa-7-azapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-6,14,17-trien-8-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-6,9,13-trimethyl-16-oxo(10,10,11-^2H₃)-5-oxa-7-azapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-6,14,17-trien-8-yl]-2-oxoethyl acetate
• Synonyms: (11β,16β)-21-(Acetyloxy)-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione-d3; Azacort-d3; Azacortinol-d3; Calcort-d3; DL 458IT-d3; Deflan-d3; Deflazacort-d3; Dezacor-d3; Dezacort-d3; Flantadin-d3; L 5458-d3; Lantadin-d3; MDL 458-d3; Oxazacort-d3; Deflazacort-d3 (Major)

Database IDs

• PubChem SID: 162259701
• PubChem CID: 71315276

CALCULATED PROPERTIES

• Acid pKa: 14.741767
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8021809
• LogD (pH = 7.4): 1.802185
• Log P: 1.8021852
• Molar Refractivity: 117.1192 cm^3
• Polarizability: 45.64737 Å^3
• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Beige Solid
• Melting Point: 252-254°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D228977

Labelled Deflazacort (D228975). A systemic corticosteroid. A derivative of prednisolone. Used for rheumatoid arthritis and lupus.

REFERENCES

• Nathansohn, G., et al.: J. Med. Chem., 10,799 (1967)
• Schiatti, P., et al.: Arzneim. Forsch., 30, 1543 (1967)
• Cavall-Perin, P., et al.: Eur. J. Clin. Pharmacol., 26, 357 (1967)
• Imbimbo, B., et al.: Adv. Exp. Med. Biol., 171, 241 (1967)