2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-6,9,13-trimethyl-16-oxo-5-oxa-7-azapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-6,14,17-trien-8-yl]-2-oxoethyl acetate

• ChemBase ID: 72815
• Molecular Formular: C25H31NO6
• Molecular Mass: 441.51674
• Monoisotopic Mass: 441.21513772
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1C[C@@H]1[C@]2(N=C(O1)C)C(=O)COC(=O)C)C)O)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-5-oxa-7-azapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-6,14,17-trien-8-yl]-2-oxoethyl acetate; 2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-6,9,13-trimethyl-16-oxo-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: zamene; deflazacort
• Synonyms: Cortax; Decortil; Deflanil; Deflazacort; (11β,16β)-21-(Acetyloxy)-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione; Azacortinol; Calcort; DL 458IT; Deflan; Deflazacort; Dezacor; Dezacort; Flantadin; L 5458; Lantadin; MDL 458; (11β,16β)-21-(acetyloxy)-11-hydroxy-2′-methyl-5′H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione; 11β,21-dihydroxy-2′-methyl-5′βH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione 2′-acetate; DL-458-IT; L-5458; azacort; oxazacort; pregna-1,4-diene-11β,21-diol-3,20-dione[17α,16α-d]-2′-methyloxazoline 21-acetate; Deflazacort

Database IDs

• CAS Number: 14484-47-0
• MDL Number: MFCD00866106
• PubChem SID: 162037736
• PubChem CID: 189821

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; DMSO: ≥20 mg/mL; Methanol
• Apperance: Off-White to Pale Yellow Solid; white to tan powder
• Melting Point: 256-258°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C25H31NO6

DETAILS

Selleck Chemicals - S1888

Research Area: Endocrinology
Biological Activity:
Deflazacort(Calcort)  is a glucocorticoid used as an anti-inflammatory and immunosuppressant.It suppresses the immune system and so it can be used to treat autoimmune diseases. Deflazacort can help to prevent and to treat the rejection of transplanted organs. It can also be used in the treatment of certain types of cancers. [1][2]

Sigma Aldrich - SML0123

Biochem/physiol Actions
Deflazacort is an anti-inflammatory and immunosuppressant glucocorticoid.

Toronto Research Chemicals - D228975

A systemic corticosteroid. A derivative of prednisolone. Used for rheumatoid arthritis and lupus.

REFERENCES

• http://en.wikipedia.org/wiki/Deflazacort
• 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)