LC-MS data of linagliptin and metabolites in plasma, urine, and feces after oral administration of 10 mg of [14C]linagliptin and intravenous infusion of 5 mg of [14C]linagliptin to healthy male volunteers
Compounds are listed in order of nominal [M + H]+ masses.
| Metabolite Code | Synthetic Reference Compound | Retention Time | [M + H]+ Formula | Product Ions [P]+ or [P]+ Formula | Found In |
|---|---|---|---|---|---|
| min | m/z (amu) | m/z (amu), [Δm (mmu)]* | |||
| M472(1) | CD10604 | 60.4 | C25H26N7O3, 472.2055 | C25H26N7O3: 472.2055 (4.2); C21H21N7O3: 419.1682 (2.4); C20H21N7O2: 391.1740 (1.7); C18H17N7O2: 363.1444 (0.0); C17H16N6O2: 336.1339 (0.4); C10H12N5O2: 234.1003 (1.2); C10N2: 158.0840 (0.4) | p.o: P, U |
| M473(1) | Linagliptin (BI1356) | 51.8 | C25H29N8O2, 473.2413 | C25H29N8O2: 473.2457 (4.4); C21H24N8O2: 420.2022**; C21H22N7O2: 404.1885 (5.0); C21H21N7O2: 403.1768 (1.1); C19H17N7O2: 375.1493 (4.9); C18H18N7O2: 364.1568 (4.6); C17H17N7O2: 351.1497 (5.3); C17H16N7O2: 350.1419 (5.4); C16H15N7O2: 337.1344 (5.7); C11H15N6O2: 263.1295 (3.9); C11H12N5O2: 246.1030 (3.9); C10H10N2: 158.0872 (2.8) | i.v.: P, U, F; p.o: P, U, F |
| M474(1) | CD1790 | 59.5 | C25H28N7O3, 474.2254 | C25H28N7O3: 474.2223 (3.1); C21H23N7O3: 421.1868 (0.6); C21H22N7O2: 404.1794 (4.1); C20H23N7O2: 393.1895 (1.8); C18H19N7O2: 365.1618 (1.8); C18H18N7O2: 364.1514 (0.8); C17H16N7O2: 350.1374 (0.9); C17H16N6O2: 336.1335**; C10H14N5O2: 236.1148 (0.1); C10H10N2: 158.0844 (0.0) | i.v.: P, U, F; p.o: P, U, F |
| M476(1) | 57.4 | C24H26N7O4, 476.2046 | C24H26N7O4: 476.2001 (4.5); C20H21N7O4: 423.1649 (0.6); C20H19N7O3: 405.1652 (10.3); C19H21N7O2: 379.1624 (13.3); C18H18N7O2: 364.1460 (6.2); C17H17N7O2: 351.1429 (1.5); C17H16N7O2: 350.1383 (1.8); C16H15N7O2: 337.1287**; C10H10N2: 158.0783 (6.1) | i.v.: U | |
| M487(1) | 54.7 | C25H27N8O3, 487.2206 | C25H27N8O3: 487.2012 (19.4); C17H17N7O2: 351.1394 (5.0); C17H16N7O2: 350.1357 (0.8); C16H15N7O2: 337.1287** | i.v.: U | |
| M489(1) | 36–40 | C25H29N8O3, 489.2363 | C25H29N8O3: 489.2363**; C25H27N8O2: 471.2231 (2.6); C21H24N8O2: 420.2001 (2.1); C21H21N7O2: 403.1746 (1.1); C19H17N7O2: 375.1451 (0.7); C18H18N7O2: 364.1526 (0.4); C17H17N7O2: 351.1438 (0.6); C17H16N7O2: 350.1373 (0.8); C16H15N7O2: 337.1308 (2.1); C17H16N6O2: 336.1364 (2.9); C11H15N6O2: 263.1280 (2.4); C11H12N5O2: 246.1021 (3.0); C10H13N4O: 205.1083 (0.6); C10H10N2: 158.0846 (0.2) | i.v.: P, U, F; p.o: P, U, F | |
| M490(1) | 54.4 | C25H28N7O4, 490.2203 | C25H28N7O4: 490.2306 (10.3); C25H26N7O3: 472.2015 (8.2); C21H23N7O3: 421.1836 (2.6); C20H23N7O2: 393.1898 (1.5); C18H19N7O2: 365.1600 (0.0); C17H17N7O2: 351.1448 (0.4); C17H16N6O2: 336.1335**; C10H14N5O2: 236.1168 (2.1) | i.v.: U; p.o: U, F | |
| M503(1) | 31.3 | C25H27N8O4, 503.2155 | C24H27N8O2: 459.2212 (4.5); C20H23N8O2: 407.1948 (0.4); C20H22N8O2: 406.1835 (3.1); C20H20N7O2: 390.1682 (0.4); C20H19N7O2: 389.1610 (1.0); C18H15N7O2: 361.1290 (0.3); C17H16N7O2: 350.1378 (1.3); C16H15N7O2: 337.1295 (0.8); C11H15N6O2: 263.1256**; C11H12N5O2: 246.0966 (2.5); C10H13N4O: 205.1077 (1.2) | i.v.: U, F; p.o: U, F | |
| M504(2) | 53.2 | C25H26N7O5, 504.1995 | C25H26N7O5: 504.1987 (0.8); C21H21N7O5: 451.1710 (10.6); C17H16N7O2: 350.1365** | p.o: U | |
| M506(1) | 54.4 | C25H28N7O5, 506.2152 | C25H28N7O5: 506.1952 (20.0); C24H26N7O3: 460.2152 (5.5); C21H22N7O4: 436.1588 (14.5); C19H21N7O2: 379.1758 (0.1); C17H17N7O2: 351.1444**; C17H16N7O2: 350.1354 (1.1); C16H15N7O2: 337.1280 (0.7); C8H9N2O: 149.0715 (0.0) | i.v.: F; p.o: F | |
| M515(1) | 58.8 | C27H31N8O3, 515.2519 | C27H31N8O3: 515.2503 (1.6); C23H26N8O3: 462.2097 (3.1); C21H24N8O2: 420.1919 (10.3); C21H22N7O2: 404.1907 (7.2); C21H21N7O2: 403.1757**; C17H16N7O2: 350.1380 (1.5); C11H12N5O2: 246.1064 (7.3) | i.v.: U; p.o: U | |
| M531(1) | 54.7 | C27H31N8O4, 531.2468 | C27H31N8O4: 531.2483 (1.5); C23H26N8O3: 462.2103 (2.5); C21H21N7O2: 403.1757**; C17H16N7O2: 350.1366 (0.1); C16H15N7O2: 337.1204 (8.3) | i.v: U p.o: F | |
| M531(2) | 55.2 | C27H31N8O4, 531.2468 | C27H31N8O4: 531.2580 (11.2); C23H26N8O4: 478.2077**; C21H22N7O3: 420.1800 (1.6); C21H21N7O3: 419.1715 (0.9); C17H16N7O2: 350.1388 (2.3); C16H15N7O2: 337.1302 (1.5) | i.v: U; p.o: F | |
| M620(1) | 52.8 | unknown, BI1356 + 147 mu | [M+H-H2O-C4H5]+: 549.2270 (6.0); C25H29N8O2: 473.2413**; C21H24N8O2: 420.2044 (2.2); C21H21N7O2 403.1795 (3.8); C17H16N7O2: 350.1414 (4.9); C16H15N7O2: 337.1334 (4.7); C11H15N6O2: 263.1306 (5.0) | i.v: U | |
| M636(2) | 45.6 | C30H38N9O5S, 636.2717 | C26H31N9O4S: 565.2184 (7.2); C25H29N8O2: 473.2406 (2.7); C21H24N8O2: 420.2022**; C21H21N7O2: 403.1720 (3.7); C17H16N7O2: 350.1403 (0.5); C11H15N6O2: 263.1251 (0.5); C10H10N2: 158.0771 (7.3) | i.v: U | |
| M650(1) | 54.5 | M474(1) + Glucuronic acid | C31H36N7O9: 650.2585 (1.0); C25H28N7O3: 474.2254**; C21H23N7O3: 421.1884 (2.2); C20H23N7O2: 393.1979 (6.6); C18H19N7O2: 365.1553 (4.7); C17H16N6O2: 336.1352 (1.7) | i.v: P; p.o: U, P | |
| M665(3) | 30.6 | C31H37N8O9, 665.2684 | C31H37N8O9: 665.2690 (0.6); C25H29N8O3: 489.2363**; C21H24N8O3: 436.2011 (4.0) | i.v: U, P; p.o: U | |
| M665(8) | 54.4 | C31H37N8O9, 665.2684 | C31H37N8O9: 665.3***; C25H29N8O3: 489.2***; C21H24N8O3: 436.2*** | i.v: U, P; p.o: U, P | |
| M716(1) | 45.1 | C30H38N9O8S2, 716.2285 | C25H29N8O2: 473.2413**; C21H24N8O2: 420.2031 (0.9); C21H21N7O2: 403.1760 (0.3); | i.v: U |