A CCR5 antagonist
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Vicriviroc (maleate)

Item No. 28453

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-piperidine, 2Z-butenedioate
CAS Number
599179-03-0
Synonyms
  • SCH 417690
Molecular Formula
C28H38F3N5O2 • C4H4O4
Formula Weight
649.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleDMSO: slightly, heatedMethanol: slightly soluble
SMILES
FC(F)(F)C1=CC=C([C@@H](N2CCN(C3(C)CCN(C(C4=C(C)N=CN=C4C)=O)CC3)C[C@@H]2C)COC)C=C1.OC(/C=C\C(O)=O)=O
InChi Code
InChI=1S/C28H38F3N5O2.C4H4O4/c1-19-16-35(14-15-36(19)24(17-38-5)22-6-8-23(9-7-22)28(29,30)31)27(4)10-12-34(13-11-27)26(37)25-20(2)32-18-33-21(25)3;5-3(6)1-2-4(7)8/h6-9,18-19,24H,10-17H2,1-5H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t19-,24-;/m0./s1
InChi Key
GXINKQQWHLIBJA-UCIBKFKQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Vicriviroc is a chemokine (C-C motif) receptor 5 (CCR5) antagonist (Ki = 2.5 nM).1 It selectively inhibits CCR5 over M1 and M2 muscarinic acetylcholine receptors (Kis = >10,000 nM for both) and human-ether-a-go-go (hERG) potassium channels (IC50 = 5.8 µM).1 Vicriviroc decreases chemotaxis induced by chemokine (C-C motif) ligand 3 (CCL3) in Ba/F3 cells expressing recombinant human CCR5 with an IC50 value of 0.91 nM.2 It inhibits the replication of 30 R5-tropic HIV-1 clinical isolates in peripheral blood mononuclear cells (PBMCs; EC50s = 0.04-1.4 nM) and reduces viral entry of seven drug-resistant strains of HIV-1 in U87 cells expressing CD4 and CCR5 (EC50s = 8.7-32.9 nM).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tagat, J.R., McCombie, S.W., Nazareno, D., et al. Piperazine-based CCR5 antagonists as HIV-1 inhibitors. IV. Discovery of 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-[4-[2-methoxy-1(R)-4-(trifluoromethyl)phenyl]ethyl-3(S)-methyl-1-piperazinyl]-4-methylpiperidine (Sch-417690/Sch-D), a potent, highly selective, and orally bioavailable CCR5 antagonist. J. Med. Chem. 47(10), 2405-2408 (2004).

    2. Strizki, J.M., Tremblay, C., Xu, S., et al. Discovery and characterization of vicriviroc (SCH 417690), a CCR5 antagonist with potent activity against human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 49(12), 4911-4919 (2005).