{2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}phosphonic acid

• ChemBase ID: 166727
• Molecular Formular: C22H30FO8P
• Molecular Mass: 472.4409642
• Monoisotopic Mass: 472.16623277
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)COP(=O)(O)O)O)C)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)COP(=O)(O)O)C)C)C
• InChI: InChI=1S/C22H30FO8P/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)21(15,23)17(25)10-20(16,3)22(12,27)18(26)11-31-32(28,29)30/h6-7,9,12,15-17,25,27H,4-5,8,10-11H2,1-3H3,(H2,28,29,30)/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
• InChIKey: VQODGRNSFPNSQE-CXSFZGCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}phosphonic acid
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethoxyphosphonic acid
• Synonyms: (11β,16α)-9-Fluoro-11,17-dihydroxy-16-methyl-21-(phosphonooxy)pregna-1,4-diene-3,20-dione; 9-Fluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-Phosphate; Betnelan Phosphate; Dexamethasone 21-Dihydrogen Phosphate; Dexamethasone 21-Phosphate; Dexamethasone Orthophosphate; Micromethason; Wymesone; Dexamethasone Phosphate

Database IDs

• CAS Number: 312-93-6
• PubChem SID: 162260860
• PubChem CID: 9400

CALCULATED PROPERTIES

• Acid pKa: 1.175686
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.8912381
• LogD (pH = 7.4): -2.0118082
• Log P: 1.5580037
• Molar Refractivity: 113.3658 cm^3
• Polarizability: 44.06103 Å^3
• Polar Surface Area: 141.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D298835

A pro-drug of Dexamethasone (D298800), an anti-inflammatory glucocorticoid. It was found that liposomal DXM-P inhibited both chronic inflammation and joint destruction, whereas free DXM-P failed to prevent joint destruction.

REFERENCES

• Kodelja, V., et al.: J. Immunol., 160, 1411 (1998)
• Metselaar, J., et al.: Arthritis Rheum., 48, 2059 (1998)
• Buttgereit, F., et al.: Arthritis Rheum., 50, 3408 (1998)
• Martinez, F., et al.: Front Biosci., 13, 453 (1998)