Table 1.

Human sEH IC₅₀ and solubility, melting point and permeability values for known adamantane inhibitors AR9281, t-AUCB and 3, and their oxygen analogs 12, 14 and 7.

Compounds		X	h sEH IC50 (nM)[a]	Solubility (μM)[b]	Melting Point (°C)	Permeability (Caco-2)
						Papp (nm/s)		ER[c]
						A→B	B→A
	1, AR9281 (UC1153)	CH2	8.0	24	202–204[d]	2.2	141.2	64.5
	12	O	29.9	59	172–173	22.4	94.5	4.3
	2, t-AUCB	CH2	0.5	25	250–255[e]	1.9	210.3	111
	14	O	9.0	>100	255–257	1.4	75.5	55.4
	3	CH2	7.7	16	216–219	6.7	4.6	0.69
	7	O	21.3	27	196–198	168	151	0.9

^aIC₅₀ values are the average of three replicates. The fluorescent assay as performed here has a standard error between 10 and 20% suggesting that differences of two-fold or greater are significant. Because of the limitations of the assay, it is difficult to distinguish among potencies < 0.5 nM.²⁵

^bSolubility in a 1% DMSO: 99% PBS buffer solution, see Experimental Section for details.

^cThe efflux ratio was calculated as ER = (Papp B→A) / (Papp A→B). See the Experimental Section for further details.

^dTaken from reference 27.

^eTaken from reference 16.