AMG-487
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MedKoo CAT#: 206468

CAS#: 473719-41-4

Description: AMG 487 is a potent and selective antagonist of chemokine (C-X-C motif) receptor 3 (CXCR3) with IC50 values of 8nM and 8.2nM for I-IP-10 and I-ITAC, respectively. AMG 487 prevents the chemokines I-IP-10 and I-ITAC from binding to CXCR3. In the cellular assays, AMG 487 inhibits CXCR3-mediated cell migration with IC50 values of 8nM, 15nM and 36nM for I-IP-10, I-ITAC and MIG, respectively.


Chemical Structure

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AMG-487
CAS# 473719-41-4

Theoretical Analysis

MedKoo Cat#: 206468
Name: AMG-487
CAS#: 473719-41-4
Chemical Formula: C32H28F3N5O4
Exact Mass: 603.20934
Molecular Weight: 603.6
Elemental Analysis: C, 63.68; H, 4.68; F, 9.44; N, 11.60; O, 10.60

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Size Price Availability Quantity
5.0mg USD 85.0 Same day
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
200.0mg USD 1250.0 Same day
500.0mg USD 2150.0 Same day
1.0g USD 3150.0 Same day
2.0g USD 5450.0 Same day
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Synonym: AMG-487; AMG 487; AMG487.

IUPAC/Chemical Name: N-[(1R)-1-[3-(4-ethoxyphenyl)-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-N-(pyridin-3-ylmethyl)-2-[4-(trifluoromethoxy)phenyl]acetamide

InChi Key: WQTKNBPCJKRYPA-UHFFFAOYSA-N

InChi Code: InChI=1S/C32H28F3N5O4/c1-3-43-25-14-10-24(11-15-25)40-30(38-29-27(31(40)42)7-5-17-37-29)21(2)39(20-23-6-4-16-36-19-23)28(41)18-22-8-12-26(13-9-22)44-32(33,34)35/h4-17,19,21H,3,18,20H2,1-2H3

SMILES Code: CCOC1=CC=C(C=C1)N2C(=O)C3=C(N=CC=C3)N=C2C(C)N(CC4=CN=CC=C4)C(=O)CC5=CC=C(C=C5)OC(F)(F)F

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 603.6 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Henne KR, 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. 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. Drug Metab Dispos. 2012 Jul;40(7):1429-40. doi: 10.1124/dmd.112.045708. Epub 2012 Apr 19. PubMed PMID: 22517972.

2: Laragione T, Brenner M, Sherry B, Gulko PS. CXCL10 and its receptor CXCR3 regulate synovial fibroblast invasion in rheumatoid arthritis. Arthritis Rheum. 2011 Nov;63(11):3274-83. doi: 10.1002/art.30573. PubMed PMID: 21811993; PubMed Central PMCID: PMC3205193.

3: Liu J, Fu Z, Li AR, Johnson M, Zhu L, Marcus A, Danao J, Sullivan T, Tonn G, Collins T, Medina J. Optimization of a series of quinazolinone-derived antagonists of CXCR3. Bioorg Med Chem Lett. 2009 Sep 1;19(17):5114-8. doi: 10.1016/j.bmcl.2009.07.032. Epub 2009 Jul 10. PubMed PMID: 19632842.

4: Pradelli E, Karimdjee-Soilihi B, Michiels JF, Ricci JE, Millet MA, Vandenbos F, Sullivan TJ, Collins TL, Johnson MG, Medina JC, Kleinerman ES, Schmid-Alliana A, Schmid-Antomarchi H. Antagonism of chemokine receptor CXCR3 inhibits osteosarcoma metastasis to lungs. Int J Cancer. 2009 Dec 1;125(11):2586-94. doi: 10.1002/ijc.24665. PubMed PMID: 19544560; PubMed Central PMCID: PMC2772145.

5: Cambien B, Karimdjee BF, Richard-Fiardo P, Bziouech H, Barthel R, Millet MA, Martini V, Birnbaum D, Scoazec JY, Abello J, Al Saati T, Johnson MG, Sullivan TJ, Medina JC, Collins TL, Schmid-Alliana A, Schmid-Antomarchi H. Organ-specific inhibition of metastatic colon carcinoma by CXCR3 antagonism. Br J Cancer. 2009 Jun 2;100(11):1755-64. doi: 10.1038/sj.bjc.6605078. Epub 2009 May 12. PubMed PMID: 19436305; PubMed Central PMCID: PMC2695685.

6: Tonn GR, 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. 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]-ethy l}-N-pyridin-3-yl-methyl-2-(4-trifluoromethoxy-phenyl)-acetamide (AMG 487) in human subjects after multiple dosing. Drug Metab Dispos. 2009 Mar;37(3):502-13. doi: 10.1124/dmd.108.021931. Epub 2008 Dec 16. PubMed PMID: 19088267.

7: Cameron CM, Cameron MJ, Bermejo-Martin JF, Ran L, Xu L, Turner PV, Ran R, Danesh A, Fang Y, Chan PK, Mytle N, Sullivan TJ, Collins TL, Johnson MG, Medina JC, Rowe T, Kelvin DJ. Gene expression analysis of host innate immune responses during Lethal H5N1 infection in ferrets. J Virol. 2008 Nov;82(22):11308-17. doi: 10.1128/JVI.00691-08. Epub 2008 Aug 6. PubMed PMID: 18684821; PubMed Central PMCID: PMC2573250.

8: Wijtmans M, Verzijl D, Leurs R, de Esch IJ, Smit MJ. Towards small-molecule CXCR3 ligands with clinical potential. ChemMedChem. 2008 Jun;3(6):861-72. doi: 10.1002/cmdc.200700365. Review. PubMed PMID: 18442035.

9: Walser TC, Rifat S, Ma X, Kundu N, Ward C, Goloubeva O, Johnson MG, Medina JC, Collins TL, Fulton AM. Antagonism of CXCR3 inhibits lung metastasis in a murine model of metastatic breast cancer. Cancer Res. 2006 Aug 1;66(15):7701-7. PubMed PMID: 16885372.