TABLE 4

Retention time, molecular ion and characteristic fragment ions of paritaprevir and metabolites in human plasma, urine, or feces

Compound	Approx. RTMin	Obs.[M+H]⁺	Calc.[M+H]⁺	Δppm	Metabolite ID	Key Fragment Ionsm/z
Paritaprevir	50.4	766.3003	766.3017	−1.8	Parent drug	571, 553, 543, 458, 450, 422, 406, 355
M29	39.1	663.2916	663.2926	−1.5	Sulfonamide hydrolysis	468, 450, 440, 422, 303
M2	37.9	782.2949	782.2967	−2.3	Parent drug + O	587, 559, 502, 474, 422, 327
M6	35.8	782.2951	782.2967	−2.1	Parent drug + O	764, 618, 587, 569, 559, 541, 474
M3	32.1	798.2900	798.2916	−2.0	Parent drug + 2O	603, 575, 518, 490, 422
M13	∼3	139.0498	139.0502	−3.1	5-Methylpyrazine-2-carboxylic acid	121, 95
Fecal-specific metabolites^#
M14	34.6	679.2863	679.2875	−1.8	M29 + O	468, 440, 422, 373, 355, 303
M15	34.1	798.2894	798.2916	−2.8	Parent drug + 2O	780, 603, 585, 518, 438, 420
M16	33.1	679.2863	679.2875	−1.8	M29 + O	484, 468, 456, 319
M17	32.8	798.2894	798.2916	−2.8	Parent drug + 2O	603, 575, 557, 518, 490, 422, 327
M18	32.5	679.2863	679.2875	−1.8	M29 + O	484, 466, 456, 438, 371, 303
M19	31.8	679.2863	679.2875	−1.8	M29 + O	468, 450, 440, 422, 355, 303, 258
M20	30.1	798.2894	798.2916	−2.8	Parent drug + 2O	587, 559, 502, 474, 422
M21	28.9	679.2863	679.2875	−1.8	M29 + O	661, 617, 484, 466
M22	22.1	697.2965	697.2975	−1.4	M29 + O + H₂O	Accurate mass only
M23	21.7	697.2965	697.2975	−1.4	M29 + O + H₂O	679, 468, 450, 440, 303
M24	18.9	903.3148	903.3164	−1.8	Parent + O + cysteine	885, 867, 782, 764, 690, 569, 541, 457, 422
M25	36.1	646.2683	646.2694	−1.7	Amide hydrolysis	525, 497, 451, 423, 406, 345, 330, 302
M26	23.9	543.2591	543.2602	−2.0	Amide hydrolysis of M29	348, 320, 304, 302, 287

Approx., approximately; Calc., calculated; ID, identification; Obs., observed; RT, retention time.
↵# Observed only in fecal samples.