(1S,2R,10S,11S,14R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxo-14-[2-(propanoyloxy)acetyl]tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl butanoate

• ChemBase ID: 170056
• Molecular Formular: C28H40O7
• Molecular Mass: 488.613
• Monoisotopic Mass: 488.27740362
• SMILES: C1CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)COC(=O)CC)OC(=O)CCC)C)C
• Canonical SMILES: CCCC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C(=O)COC(=O)CC
• InChI: InChI=1S/C28H40O7/c1-5-7-24(33)35-28(22(31)16-34-23(32)6-2)13-11-20-19-9-8-17-14-18(29)10-12-26(17,3)25(19)21(30)15-27(20,28)4/h14,19-21,25,30H,5-13,15-16H2,1-4H3/t19-,20-,21-,25+,26-,27-,28-/m0/s1
• InChIKey: FOGXJPFPZOHSQS-AYVLZSQQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxo-14-[2-(propanoyloxy)acetyl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl butanoate
• IUPAC Traditional name: pandel
• Synonyms: (11β)-11-Hydroxy-17-(1-oxobutoxy)-21-(1-oxopropoxy)pregn-4-ene-3,20-dione; 17α-Butyryloxy-11β-hydroxy-21-propionyloxy-4-pregnene-3,20-dione; Hydrocortisone Buteprate; Hydrocortisone Probutate; Pandel; TS 408; Hydrocortisone 17-Butyrate 21-Propionate

Database IDs

• CAS Number: 72590-77-3
• PubChem SID: 164225966
• PubChem CID: 636398

CALCULATED PROPERTIES

• Acid pKa: 14.812843
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.0030575
• LogD (pH = 7.4): 4.0030575
• Log P: 4.0030575
• Molar Refractivity: 129.5578 cm^3
• Polarizability: 51.480667 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H714665

A synthetic adrenocorticosteroid that acts as an anti-inflammatory and anti-pruritic agents. It is used as a topical for the treatment of dermatologic disorders such as atopic dermatitis and psoriasis.

REFERENCES

• Mason, J. et al.: Br. J. Dermatol., 146, 351 (2002)
• Sears, H.W. et al.: Clin. Therap., 19, 710 (2002)
• Otomo, Y.Z. et al.: Nip. Yakur. Zas., 78, 647 (2002)