(±)-AMG 487 - CAS 473719-41-4
Not Intended for Therapeutic Use. For research use only.
Product Name:
(±)-AMG 487
Catalog Number:
Benzeneacetamide, N-((1R)-1-(3-(4-ethoxyphenyl)-3,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-2-yl)ethyl)-N-(3-pyridinylmethyl)-4-(trifluoromethoxy)-; N-[(1R)-1-[3-(4-ethoxyphenyl)-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-N-(pyridin-3-ylmethyl)-2-[4-(trifluorome
CAS Number:
CXCR3 antagonist; Inhibits cell migration and metastasis
Molecular Weight:
Molecular Formula:
Quality Standard:
Canonical SMILES:
Chemical Structure
CAS 473719-41-4 (±)-AMG 487

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Reference Reading

1.An inhibitory metabolite leads to dose- and time-dependent pharmacokinetics of (R)-N-{1-[3-(4-ethoxy-phenyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-N-pyridin-3-yl-methyl-2-(4-trifluoromethoxy-phenyl)-acetamide (AMG 487) in human subjects after multiple dosing.
Tonn GR1, Wong SG, Wong SC, Johnson MG, Ma J, Cho R, Floren LC, Kersey K, Berry K, Marcus AP, Wang X, Van Lengerich B, Medina JC, Pearson PG, Wong BK. Drug Metab Dispos. 2009 Mar;37(3):502-13. doi: 10.1124/dmd.108.021931. Epub 2008 Dec 16.
(R)-N-{1-[3-(4-Ethoxy-phenyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]-pyrimidin-2-yl]-ethyl}-N-pyridin-3-yl-methyl-2-(4-trifluoromethoxyphenyl)-acetamide (AMG 487) is a potent and selective orally bioavailable chemokine (C-X-C motif) receptor 3 (CXCR3) antagonist that displays dose- and time-dependent pharmacokinetics in human subjects after multiple oral dosing. Although AMG 487 exhibited linear pharmacokinetics on both days 1 and 7 at the 25-mg dose, dose- and time-dependent kinetics were evident at the two higher doses. Nonlinear kinetics were more pronounced after multiple dosing. Area under the plasma concentration-time curve from 0 to 24 h [AUC((0-24 h))] increased 96-fold with a 10-fold increase in dose on day 7 compared with a 28-fold increase in AUC((0-24 h)) on day 1. These changes were correlated with time- and dose-dependent decreases in the metabolite to parent plasma concentrations, suggesting that these changes result from a decrease in the oral clearance (CL) of AMG 487 (e.
2.Sequential metabolism of AMG 487, a novel CXCR3 antagonist, results in formation of quinone reactive metabolites that covalently modify CYP3A4 Cys239 and cause time-dependent inhibition of the enzyme.
Henne KR1, Tran TB, VandenBrink BM, Rock DA, Aidasani DK, Subramanian R, Mason AK, Stresser DM, Teffera Y, Wong SG, Johnson MG, Chen X, Tonn GR, Wong BK. Drug Metab Dispos. 2012 Jul;40(7):1429-40. doi: 10.1124/dmd.112.045708. Epub 2012 Apr 19.
CYP3A4-mediated biotransformation of (R)-N-(1-(3-(4-ethoxyphenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl)ethyl)-N-(pyridin-3-ylmethyl)-2-(4-(trifluoromethoxy)phenyl)acetamide (AMG 487) was previously shown to generate an inhibitory metabolite linked to dose- and time-dependent pharmacokinetics in humans. Although in vitro activity loss assays failed to demonstrate CYP3A4 time-dependent inhibition (TDI) with AMG 487, its M2 phenol metabolite readily produced TDI when remaining activity was assessed using either midazolam or testosterone (K(I) = 0.73-0.74 μM, k(inact) = 0.088-0.099 min(-1)). TDI investigations using an IC(50) shift method successfully produced inhibition attributable to AMG 487, but only when preincubations were extended from 30 to 90 min. The shift magnitude was ∼3× for midazolam activity, but no shift was observed for testosterone activity. Subsequent partition ratio determinations conducted for M2 using recombinant CYP3A4 showed that inactivation was a relatively inefficient process (r = 36).