(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-ethoxyacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl propanoate

• ChemBase ID: 162018
• Molecular Formular: C27H37FO6
• Molecular Mass: 476.5774832
• Monoisotopic Mass: 476.25741712
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)COCC)OC(=O)CC)C)C)O)F)C
• Canonical SMILES: CCOCC(=O)[C@@]1(OC(=O)CC)[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C27H37FO6/c1-6-23(32)34-27(22(31)15-33-7-2)16(3)12-20-19-9-8-17-13-18(29)10-11-24(17,4)26(19,28)21(30)14-25(20,27)5/h10-11,13,16,19-21,30H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,24-,25-,26-,27-/m0/s1
• InChIKey: FEZHAIGGCZLVGJ-SUYDQAKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-ethoxyacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• IUPAC Traditional name: (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-ethoxyacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• Synonyms: 21-O-Ethyl-17-O-propionylbetamethasone; (11β,16β)-21-Ethoxy-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-pregna-1,4-diene-3,20-dione; Betamethasone 17-Propionate 21-Ethoxide

Database IDs

• CAS Number: 123013-29-6
• PubChem SID: 162256153
• PubChem CID: 14749472

CALCULATED PROPERTIES

• Acid pKa: 13.640591
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.8231654
• LogD (pH = 7.4): 3.8231652
• Log P: 3.8231654
• Molar Refractivity: 125.7711 cm^3
• Polarizability: 49.032906 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - B327065

Derivative of betamethasone 17-Propionate (B327015), a degradation product of Betamethasone. Glucocorticoid.

REFERENCES

• Andersson, P., et al.: J. Pharm. Pharmacol., 36, 763 (1984)
• Wurthwein, G., et al.: Biopharm. Drug Dispos., 11, 381 (1984)
• Samtani, M., et al.: J. Pharm. Sci., 93, 726 (1984)
• Samtani, M., et al.: Drug Metab. Dispos., 33, 1124 (1984)