A CCR5 antagonist
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TAK-220

Item No. 28448

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-acetyl-N-[3-[4-[[4-(aminocarbonyl)phenyl]methyl]-1-piperidinyl]propyl]-N-(3-chloro-4-methylphenyl)-4-piperidinecarboxamide
CAS Number
333994-00-6
Molecular Formula
C31H41ClN4O3
Formula Weight
553.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
NC(C1=CC=C(CC2CCN(CCCN(C3=CC(Cl)=C(C)C=C3)C(C4CCN(C(C)=O)CC4)=O)CC2)C=C1)=O
InChi Code
InChI=1S/C31H41ClN4O3/c1-22-4-9-28(21-29(22)32)36(31(39)27-12-18-35(19-13-27)23(2)37)15-3-14-34-16-10-25(11-17-34)20-24-5-7-26(8-6-24)30(33)38/h4-9,21,25,27H,3,10-20H2,1-2H3,(H2,33,38)
InChi Key
ASSJTMUEFHUKMJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $169

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    Product Description

    TAK-220 is an orally bioavailable antagonist of chemokine (C-C motif) receptor 5 (CCR5).1 It binds to CCR5 (IC50 = 3.5 nM for the human receptor in CHO cells), but not CCR1, CCR2b, CCR3, CCR4, or CCR7.1,2 TAK-220 inhibits the binding of chemokine (C-C motif) ligand 5 (CCL5) and CCL3 to CCR5 (IC50s = 3.5 and 1.4 nM, respectively) but does not inhibit binding of CCL4.2 It inhibits HIV-1 envelope-mediated membrane fusion in a macrophage (M-tropic) R5, but not in a T cell (T-tropic) X4, strain of HIV-1 (IC50s = 0.42 and >1,000 nM, respectively). TAK-220 inhibits the replication of six strains of R5 HIV-1 clinical isolates (EC90 overall mean = 13 nM) and the R5 JR-FL laboratory-adapted strain (EC50 = 0.6 nM), but not of X4 HIV-1 clinical isolates or the X4 IIIB laboratory-adapted strain (EC50s = >10,000 nM for both), in human peripheral blood mononuclear cells (PBMCs).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Imamura, S., Ichikawa, T., Nishikawa, Y., et al. Discovery of a piperidine-4-carboxamide CCR5 antagonist (TAK-220) with highly potent Anti-HIV-1 activity. J. Med. Chem. 49(9), 2784-2793 (2006).

    2. Takashima, K., Miyake, H., Kanzaki, N., et al. Highly potent inhibition of human immunodeficiency virus type 1 replication by TAK-220, an orally bioavailable small-molecule CCR5 antagonist. Antimicrob. Agents Chemother. 49(8), 3474-3482 (2005).