2-[(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 174232
• Molecular Formular: C24H32O6
• Molecular Mass: 416.50728
• Monoisotopic Mass: 416.21988874
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](C[C@@H]2C)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)COC(=O)C)O)C)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)C
• InChI: InChI=1S/C24H32O6/c1-13-9-16-17-6-8-24(29,20(28)12-30-14(2)25)23(17,4)11-19(27)21(16)22(3)7-5-15(26)10-18(13)22/h5,7,10,13,16-17,19,21,27,29H,6,8-9,11-12H2,1-4H3/t13-,16-,17-,19-,21+,22-,23-,24-/m0/s1
• InChIKey: PLBHSZGDDKCEHR-LFYFAGGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: depo-medrol; 2-[(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• Synonyms: 21-Acetoxy-11β,17-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione; DepMedalone 40; DepMedalone 80; Depo-Medrone; NSC 48985; U 8210; Urbason Crystal Suspension; Vetacortyl; 6α-Methyl Prednisolone 21-Acetate; Depo-medrate; Depo-medrol; Methylprednisolone acetate

Database IDs

• CAS Number: 53-36-1
• PubChem SID: 164230142
• PubChem CID: 5877

CALCULATED PROPERTIES

• Acid pKa: 12.610175
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.0011344
• LogD (pH = 7.4): 2.0011318
• Log P: 2.0011344
• Molar Refractivity: 112.1934 cm^3
• Polarizability: 43.719112 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 192-195°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: ACTH antagonist; ACTH secretion inhibitor; Calcium mobilizer; Corticosteroid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Application(s): Antiinflammatory; Immunosuppressive

DETAILS

Toronto Research Chemicals - M326030

6α-Methyl Prednisolone 21-Acetate is used as a glucocorticoid.

REFERENCES

• Sugihara, N., et al: Am. J. Cardiol., 69, 1475 (1992)
• Bracken, M.B., et al.: J. Neurosurg., 89, 699 (1992)
• Dammers, J.W.H.H., et al.: Brit. Med. J., 319, 884 (1999).