chloromethyl (2R,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carboxylate

• ChemBase ID: 179716
• Molecular Formular: C24H31ClO7
• Molecular Mass: 466.95174
• Monoisotopic Mass: 466.17583101
• SMILES: [C@]12([C@](C(=O)OCCl)(OC(=O)OCC)CCC1C1C([C@@]3(C(=CC(=O)C=C3)CC1)C)[C@H](C2)O)C
• Canonical SMILES: ClCOC(=O)[C@]1(CCC2[C@]1(C)C[C@H](O)C1C2CCC2=CC(=O)C=C[C@]12C)OC(=O)OCC
• InChI: InChI=1S/C24H31ClO7/c1-4-30-21(29)32-24(20(28)31-13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)19(16)18(27)12-23(17,24)3/h7,9,11,16-19,27H,4-6,8,10,12-13H2,1-3H3/t16?,17?,18-,19?,22-,23-,24-/m0/s1
• InChIKey: DMKSVUSAATWOCU-OEWWVBLQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloromethyl (2R,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylate
• IUPAC Traditional name: chloromethyl (2R,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylate
• Synonyms: Alrex; Loteflam; Lotemax; Zylet; Loteprednol Etabonate

Database IDs

• CAS Number: 82034-46-6
• PubChem SID: 164235626
• PubChem CID: 54808

CALCULATED PROPERTIES

• Acid pKa: 14.879642
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.937488
• LogD (pH = 7.4): 3.9374878
• Log P: 3.937488
• Molar Refractivity: 118.1722 cm^3
• Polarizability: 46.392654 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Corticosteroid

Product Information

• Application(s): Antiinflammatory agent; Used in ophthalmology

REFERENCES

• Belg. Pat., 1981, Otsuka Pharm, 889 563; CA, 97, 6651n, (synth, pharmacol)
• Druzgala, P. et al., J. Steroid Biochem., 1991, 38, 149, (synth, pmr, ir)
• Bodor, N.S. et al., Steroids, 1991, 56, 434, (pharmacol)
• Bodor, N. et al., Pharm. Res., 1992, 9, 1275, (metab)
• Howes, J.F. et al., J. Ocul. Pharmacol., 1994, 10, 289, (activity)
• Graul, A., Drugs of the Future, 1997, 22, 1086