(1S,2R,10S,11S,13S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,17-dione

• ChemBase ID: 72784
• Molecular Formular: C22H28O5
• Molecular Mass: 372.45472
• Monoisotopic Mass: 372.193674
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1C[C@@H]([C@]2(O)C(=O)CO)C)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,12,15-16,19,23,27H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19+,20-,21-,22-/m0/s1
• InChIKey: PIDANAQULIKBQS-RNUIGHNZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,13S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione; (1S,2R,10S,11S,13S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione
• IUPAC Traditional name: methylprednisone
• Synonyms: Betanisona; Betapar; Meprednisone; (16β)-17,21-Dihydroxy-16-methylpregna-1,4-diene-3,11,20-trione; Meprednisone; 16β-Methylprednisone; Betalone; Betapred; Deltisona B; Methylprednisone; NSC 527579; Sch 4358; (1S,2R,10S,11S,13S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione

Database IDs

• CAS Number: 1247-42-3
• MDL Number: MFCD00083662
• PubChem SID: 162037705
• PubChem CID: 5284587

CALCULATED PROPERTIES

• Acid pKa: 12.440329
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.0234768
• LogD (pH = 7.4): 2.023473
• Log P: 2.023477
• Molar Refractivity: 102.0397 cm^3
• Polarizability: 39.331356 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 204-206°C
• Hydrophobicity(logP): 2.18

Safety Information

• Storage Condition: -20°C; Refrigerator

Product Information

• Purity: 95%
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1689

Research Area: Inflammation, Endocrinology
Biological Activity:
Betapar(Meprednisone) is a glucocorticoid and a methylated derivative of prednisone. [1]The methylprednisone to MPL area under the curve ratio decreased from 0.19 +/- 0.04 in control to 0.14 +/- 0.03 in ketoconazole-treated rats (P less than .05) due to altered interconversion between these steroids. An improved pharmacokinetic/dynamic receptor/gene-mediated model characterized the steroid receptor binding and induction of tyrosine aminotransferase activity after i.v. MPL sodium succinate (10 mg/kg). In contrast to previous in vitro studies, ketoconazole at maximally tolerated doses failed to antagonize the steroid receptor-mediated activity of MPL. [2]

Toronto Research Chemicals - M225040

Corticosteroid.

REFERENCES

• http://en.wikipedia.org/wiki/Meprednisone
• Rosenfeld, S., et al.: Blood, 85, 3058 (1995)
• Kojima, S., et al.: Br. J. Haematol., 111, 321 (1995)
• Wong, S., et al.: J. Biol. Chem., 1999, 274, 10388 (1995)
• Ding, B., et al.: Biochem. Pharmacol., 61, 665 (1995)