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. Author manuscript; available in PMC: 2014 Jul 25.
Published in final edited form as: J Med Chem. 2013 Jul 3;56(14):5917–5930. doi: 10.1021/jm4007017

Table 1.

Inhibitory Potency (IC50) and Systemic Distribution of 3’-Substituted O-Biphenyl-3-yl Carbamates.

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R In vitro IC50 (nM)a FAAH inhibition in liver (%)b FAAH inhibition in brain (%)b PSA (Å2)d
3 CONH2 2.0 91.7±0.7 −3.0±8.0 83
7a COCH3 0.3 88.1±0.8 89.2±0.6 62
7b COOH 32 30.0±2.6 2.8±1.3 77
66.4±4.1c −6.8±2.7c
7c NHCOCH3 15 76.0±1.6 31.6±1.5 72
7d CONHCH3 6.0 87.2±2.4 0.9±3.7 73
7e CON(CH3)2 1.5 84.2±2.5 22.6±7.8 65
7f SO2NH2 2.7 81.1±1.3 7.0±1.7 99
7g SO2CH3 6.3 73.9±4.6 6.6±2.3 78
11a CH3 2.5 72.1±4.9 85.4±0.5 49
11b CH(OH)CH3 2.0 80.9±0.9 89.6±0.6 65
11c CH2OH 1.6 86.6±0.6 88.6±0.7 66
a

IC50 measured in membrane preparations of Wistar rat brain

b

FAAH inhibition measured ex vivo 1 h after injection in Swiss Webster mice (1 mg/kg, intraperitoneal, n = 3)

c

FAAH inhibition measured ex vivo 1 h after injection in Swiss Webster mice (3 mg/kg, intraperitoneal, n = 3)

d

PSA values were calculated using ICM version 3.7 (Molsoft LLC, San Diego, CA).