chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14-{[(2,2,2-2H3)ethoxycarbonyl]oxy}-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carboxylate

• ChemBase ID: 172416
• Molecular Formular: C24H31ClO7
• Molecular Mass: 466.95174
• Monoisotopic Mass: 466.17583101
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)OCCl)OC(=O)OCC)C)O)C
• Canonical SMILES: ClCOC(=O)[C@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=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-HROMYWEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14-{[(2,2,2-^2H₃)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 (1S,2R,10S,11S,14R,15S,17S)-14-{[(2,2,2-^2H₃)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: (11β,17α)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-3-oxo-androsta-1,4-diene-17-carboxylic Acid-d3 Chloromethyl Ester; CDDD-5604-d3; HGP-1-d3; P-5604-d3; Alrex-d3; Lotemax-d3; Loteprednol Etabonate-d3

Database IDs

• PubChem SID: 164228326
• PubChem CID: 45039669

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

Physical Property

• Apperance: Crystalline Solid

DETAILS

Toronto Research Chemicals - L471402

Labelled Loteprednol Etabonate, an ophthalmic corticosteroid. Used as an anti-inflammatory.

REFERENCES

• Alberth, M., et al.: J. Biopharm.Sci., 2, 115 (1991)
• Bodor, N., et al.: Pharm. Res., 9, 1275 (1991)
• Bartlett, J.D., et al.: J. Ocul. Pharmacol., 9, 157 (1993)