Identification of amiodarone metabolites in human bile after oral drug administration using UPLC-Q/TOF mass spectrometry
| Metabolite | Description | Retention Time | Formula | Measured Mass | Calculated Mass | Fragment Ions |
|---|---|---|---|---|---|---|
| min | [M + H]+ | |||||
| M0 | Parent | 18.0 | C25H29I2NO3 | 646.029 | 646.032 | 372.831, 276.082, 247.078, 245.956, 217.926, 201.094, 119.021, 100.113 |
| M1 | N-Desethylation − I + H | 16.2 | C23H26INO3 | 492.108 | 492.104 | |
| M2 | N-Desethylation + hydroxylation − I + H | 13.1 | C23H26INO4 | 508.097 | 508.099 | 437.024, 419.017 |
| M3 | Parent − C6H13N | 16.3 | C19H16I2O3 | 546.925 | 546.927 | 372.858 |
| M4 | 4′-Carboxylamiodarone − I + H | 13.3 | C25H28INO5 | 550.109 | 550.109 | 276.070, 100.113 |
| M5 | Hydroxylation − C4H9N | 21.5 | C21H20I2O4 | 590.952 | 590.953 | 546.930, 372.818, 217.927, 201.091, 119.013, 91.018 |
| M6-1 | 2 × Hydroxylation − C4H9N | 14.4 | C21H20I2O5 | 606.943 | 606.948 | 562.924, 544.915, 372.830 |
| M6-2 | 2 × Hydroxylation − C4H9N | 18.6 | C21H20I2O5 | 606.943 | 606.948 | 562.925, 544.917, 372.828 |
| M7 | N-Desethylation | 17.0 | C23H25I2NO3 | 617.996 | 618.000 | 372.858, 201.090 |
| M8-1 | N-Desethylation + hydroxylation | 13.5 | C23H25I2NO4 | 633.989 | 633.995 | 372.820 |
| M8-2 | N-Desethylation + hydroxylation | 13.7 | C23H25I2NO4 | 633.992 | 633.995 | 372.821, 562.922, 544.908 |
| M8-3 | N-Desethylation + hydroxylation | 14.0 | C23H25I2NO4 | 633.994 | 633.995 | 372.822, 562.923, 544.908 |
| M8-4 | N-Desethylation + hydroxylation | 14.4 | C23H25I2NO4 | 633.997 | 633.995 | 372.821, 562.922, 544.907 |
| M8-5 | N-Desethylation + hydroxylation | 14.7 | C23H25I2NO4 | 633.990 | 633.995 | 372.824 |
| M9 | 4′-Carboxylamiodarone + N-desethylation | 13.4 | C23H23I2NO5 | 647.975 | 647.974 | |
| M10-1 | N-Desethylation + dihydroxylation | 11.6 | C23H25I2NO5 | 649.985 | 649.990 | 372.823, 245.923, 217.928, 119.016, 91.020 |
| M10-2 | N-Desethylation + dihydroxylation | 12.0 | C23H25I2NO5 | 649.988 | 649.990 | 372.822, 245.925, 217.922, 119.013, 91.021 |
| M11-1 | 4′-Hydroxylation | 14.3 | C25H29I2NO4 | 662.026 | 662.026 | 372.858, 100.113 |
| M11-2 | 3′-Hydroxylation | 14.5 | C25H29I2NO4 | 662.024 | 662.026 | 372.824, 100.114 |
| M11-3 | Hydroxylation | 14.9 | C25H29I2NO4 | 662.024 | 662.026 | |
| M11-4 | Hydroxylation | 15.3 | C25H29I2NO4 | 662.025 | 662.026 | |
| M11-5 | 2-Hydroxylation | 15.5 | C25H29I2NO4 | 662.023 | 662.026 | 372.822, 100.114 |
| M12 | 4′-Carboxylamiodarone | 14.2 | C25H27I2NO5 | 676.002 | 676.006 | 372.823, 245.926, 217.925, 100.122 |
| M13 | 4′-Carboxylamiodarone + glucuronidation − I + H | 11.9 | C31H36INO11 | 726.139 | 726.141 | 550.112 |
| M14 | Hydroxylation + glucuronidation − C4H9N | 18.1 | C27H28I2O10 | 766.987 | 766.985 | 590.954, 546.930 |
| M15-1 | N-Desethylation + hydroxylation + glucuronidation | 12.2 | C29H33I2NO10 | 810.028 | 810.027 | 633.998, 562.931, 544.912 |
| M15-2 | N-Desethylation + hydroxylation + glucuronidation | 19.6 | C29H33I2NO10 | 810.027 | 810.027 | 633.997, 372.824 |
| M16 | N-Glucuronidation | 16.3 | C31H37I2NO9 | 822.061 | 822.064 | 646.024 |
| M17 | N-Desethylation + 4′-Carboxylamiodarone + glucuronidation | 12.1 | C29H31I2NO11 | 824.012 | 824.007 | 647.980 |
| M18-1 | Hydroxylation + glucuronidation | 12.6 | C31H37I2NO10 | 838.050 | 838.059 | 662.027, 372.825, 100.113 |
| M18-2 | Hydroxylation + glucuronidation | 12.8 | C31H37I2NO10 | 838.059 | 838.059 | 662.025, 372.823, 100.114 |
| M18-3 | Hydroxylation + glucuronidation | 13.0 | C31H37I2NO10 | 838.060 | 838.059 | 662.028, 372.822, 100.115 |
| M19-1 | 4′-Carboxylamiodarone + glucuronidation | 12.4 | C31H35I2NO11 | 852.035 | 852.038 | 676.009 |
| M19-2 | 4′-Carboxylamiodarone + glucuronidation | 12.9 | C31H35I2NO11 | 852.044 | 852.038 | 676.008 |