An antagonist of CCR5 and CCR2
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Cenicriviroc

Item No. 23927

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-[4-(2-butoxyethoxy)phenyl]-1,2,3,4-tetrahydro-1-(2-methylpropyl)-N-[4-[(S)-[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl]phenyl]-1-benzazocine-5-carboxamide
CAS Number
497223-25-3
Synonyms
  • TAK-652
Molecular Formula
C41H52N4O4S
Formula Weight
696.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
295 nm
SMILES
CCCCOCCOC1=CC=C(C2=CC=C(N(CC(C)C)CCC/C(C(NC3=CC=C([S@](CC4=CN=CN4CCC)=O)C=C3)=O)=C\5)C5=C2)C=C1
InChi Code
InChI=1S/C41H52N4O4S/c1-5-7-22-48-23-24-49-38-15-10-32(11-16-38)33-12-19-40-35(25-33)26-34(9-8-21-44(40)28-31(3)4)41(46)43-36-13-17-39(18-14-36)50(47)29-37-27-42-30-45(37)20-6-2/h10-19,25-27,30-31H,5-9,20-24,28-29H2,1-4H3,(H,43,46)/b34-26+/t50-/m0/s1
InChi Key
PNDKCRDVVKJPKG-WHERJAGFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    5 mg

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    10 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Cenicriviroc is an orally bioavailable antagonist of C-C chemokine receptor type 5 (CCR5) and CCR2 that inhibits binding of macrophage inflammatory protein 1α (MIP-1α; IC50 = 2.3 nM) and monocyte chemotactic protein 1 (MCP-1; IC50 = 5.9 nM), respectively, in CHO cells.1 Cenicriviroc is also an antagonist of CCR3 and CCR4 (IC50s = 2.4 and 1.1 μM, respectively), however, it does not inhibit agonist binding to CCR1 or CCR7 at concentrations up to 10 μM. At a concentration of 100 nM, cenicriviroc completely inhibits replication of R5 HIV-1 in U87.CD4.CCR5 cells. Cenicriviroc inhibits replication of the R5 HIV-1 strains JR-FL and KK in peripheral blood mononuclear cells (PBMCs) with EC50 values ranging from 21 to 210 pM and 33 to 91 pM, respectively. In vivo, cenicriviroc (20 mg/kg per day) reduces collagen deposition, levels of collagen type 1 protein and mRNA expression, and non-alcoholic fatty liver disease activity score in a mouse model of non-alcoholic steatohepatitis (NASH).2 It also reduces collagen type 1 protein levels, mRNA expression, and collagen deposition in a mouse model of unilateral ureter obstruction and a rat model of thioacetamide-induced liver fibrosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Baba, M., Takashima, K., Miyake, H., et al. TAK-652 inhibits CCR5-mediated human immunodeficiency virus type 1 infection in vitro and has favorable pharmacokinetics in humans. Antimicrob. Agents Chemother. 49(11), 4584-4591 (2005).

    2. Lefebvre, E., Moyle, G., Reshef, R., et al. Antifibrotic effects of the dual CCR2/CCR5 antagonist cenicriviroc in animal models of liver and kidney fibrosis. PLoS One 11(6):e0158156, (2016).