TABLE 6

Physicochemical properties, abundance and estimated fm of carboxylic acid metabolites

Structures of drugs and their metabolites are provided in Supplemental Table 5. References provided in Supplemental Material.

Drug	cLogD	tPSA	Metabolite	cLogD	tPSA	M/P	f_m	Ref.
Azimilide	2.66	72.6	Carboxylic acid	1.05	50.4	4	0.35	Riley et al., 2005
Celecoxib	2.59	83.4	Carboxylic acid metabolite	−1.77	124	1	0.73	Paulson et al., 2000; Kirchheiner et al., 2003a
Losartan	1.48	92.5	Carboxylosartan	−0.06	110	4.4	0.14	Lo et al., 1995; Neves et al., 2008
Metoprolol	−0.47	50.7	O-Desmethylmetoprolol carboxylic acid	−1.65	78.8	6.5		Cerqueira et al., 2005
Montelukast	3.2	95.7	Montelukast carboxylic acid	0.21	133	0.24		Karonen et al., 2012
Nabumetone	3.14	26.3	6-Methoxynapthyl carboxylic acid	−0.45	46.5	>1		Nobilis et al., 2003
Quetiapine	2.51	73.6	Quetiapine carboxylic acid	−1.13	90.7	0.63		Gefvert et al., 1998; DeVane and Nemeroff, 2001
Ranolazine	1.28	74.3	Cleaved carboxylic acid	−3.12	76	0.25		Abdallah and Jerling, 2005; Jerling and Abdallah, 2005; Jerling et al., 2005
Regaplinide	1.99	78.9	Carboxylic acid metabolite	−1.86	125	0.05	0.66	van Heiningen et al., 1999; Honkalammi et al., 2011
Terfenadine	3.6	43.7	Fexofenadine	1.23	81	98		Abernethy et al., 2001
Zolmitriptan	−1.47	57.4	Zolmitriptan indoleacetic acid	−3.4	91.4	1.3	0.31	Dixon et al., 1997; Seaber et al., 1997