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| 5mg |
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| 25mg |
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Purity: ≥98%
Cenicriviroc (formerly known as TAK-652 or TBR-652) is a novel, orally bioactive, and dual antagonist of CCR2/CCR5, it also inhibits both HIV-1 and HIV-2, and has the potential for the treatment of HIV infection. TAK-652 prevented macrophage inflammatory protein 1alpha (MIP-1alpha), MIP-1beta, and RANTES (regulated on activation, normal T-cell expressed and secreted) from attaching to CCR5-expressing cells at nanomolar concentrations. Additionally, monocyte chemotactic protein 1 (MCP-1) binding to cells expressing CCR2b may be inhibited by TAK-652. It did, however, have a limited inhibitory effect on ligand binding to other chemokine receptors. TAK-652 was completely inactive against HIV-1 that used CXCR4 (X4) but active against HIV-1 that used CCR5 (R5).
| Targets |
CCR5 ( IC50 = 0.29 nM ); CCR2 ( IC50 = 5.9 nM ); R5 HIV-1 ( IC50 = 0.024-0.08 nM ); R5 HIV-2 ( IC50 = 0.03-0.98 nM )
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| Enzyme Assay |
Cenicriviroc blocks HIV-1 from entering cells at an effective concentration of 50% EC50 of 0.03, 0.33, 0.45, and 0.98 nM for the four R5 HIV-2 clinical isolates that were tested. Cenicriviroc resistance in the dual-tropic and X4-tropic HIV-2 strains is >1000 nM for EC50 and 33% and 4% for MPI, respectively.
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| Cell Assay |
Male C57BL/6 mice receive an intraperitoneal injection of TG, and 48 hours later, peritoneal lavage is used to collect activated macrophages. A Transwell1 Chamber with a 5 μm-pore size polycarbonate filter is used to assay chemotaxis. Briefly put, cells are cultured for two hours with 1 nM CCL2 and/or 1 μM Cenicriviroc (dissolved in 0.5% acetic acid dimethyl sulfoxide and diluted 1:1000 with serum-free Roswell Park Memorial Institute-1640 medium and 0.5% bovine serum albumin). Using a 3-laser BD FACSCanto, cells are extracted from the lower compartment and subjected to flow cytometry analysis in order to count the number of F4/80+CD11b+ macrophages. The software FlowJo is used to analyze the results.
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| References |
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| Molecular Formula |
C41H52N4O4S
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| Molecular Weight |
696.94
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| Exact Mass |
696.37
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| Elemental Analysis |
C, 70.66; H, 7.52; N, 8.04; O, 9.18; S, 4.60
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| CAS # |
497223-25-3
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| Related CAS # |
Cenicriviroc Mesylate; 497223-28-6
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| Appearance |
Solid powder
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| SMILES |
CCCCOCCOC1=CC=C(C=C1)C2=CC/3=C(C=C2)N(CCC/C(=C3)/C(=O)NC4=CC=C(C=C4)[S@@](=O)CC5=CN=CN5CCC)CC(C)C
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| InChi Key |
PNDKCRDVVKJPKG-WHERJAGFSA-N
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| 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
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| Chemical Name |
(5E)-8-[4-(2-butoxyethoxy)phenyl]-1-(2-methylpropyl)-N-[4-[(S)-(3-propylimidazol-4-yl)methylsulfinyl]phenyl]-3,4-dihydro-2H-1-benzazocine-5-carboxamide
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.98 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (2.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4348 mL | 7.1742 mL | 14.3484 mL | |
| 5 mM | 0.2870 mL | 1.4348 mL | 2.8697 mL | |
| 10 mM | 0.1435 mL | 0.7174 mL | 1.4348 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05630885 | Active Recruiting |
Drug: CVC 150 mg Drug: CVC 300 mg |
HIV-1-infection | National Institute of Allergy and Infectious Diseases (NIAID) |
May 30, 2023 | Phase 2 |
| NCT02128828 | Completed | Drug: cenicriviroc | Human Immunodeficiency Virus AIDS Dementia Complex |
University of Hawaii | April 2014 | Phase 2 |
| NCT03376841 | Completed | Drug: Cenicriviroc | Hepatic Impairment | Allergan | June 6, 2017 | Phase 1 |
| NCT01827540 | Completed | Drug: Cenicriviroc Drug: Dolutegravir Drug: Midazolam |
HIV-infection/AIDS | Tobira Therapeutics, Inc. | March 2013 | Phase 1 |
| NCT02342067 | Completed | Drug: Cenicriviroc Drug: Pioglitazone |
Healthy | Tobira Therapeutics, Inc. | March 2015 | Phase 1 |
 Inhibitory effect of TAK-652 on binding of RANTES (A), MIP-1α (B), and MIP-1β (C) to CCR5.Antimicrob Agents Chemother.2005 Nov;49(11):4584-91. |
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 Inhibitory effect of TAK-652 on ligand binding to various chemokine receptors.CHO cells expressing CCR1 (open circles), CCR2b (open squares), CCR3 (filled triangles), CCR4 (open triangles), or CCR7 (filled circles) were incubated with various concentrations of TAK-652 in binding buffer containing125I-labeled RANTES, MCP-1, eotaxin, TARC, or MIP-3β, respectively. Binding reactions were performed at room temperature and terminated by washing out the cell-free ligand with PBS. The cell-associated radioactivity was measured with a scintillation counter. Data represent means ± standard deviations for triplicate wells.Antimicrob Agents Chemother.2005 Nov;49(11):4584-91. |
 Antiviral activity of TAK-652 against R5X4 HIV-1 in U87.CD4.CCR5 and U87.CD4.CXCR4 cells. The cells were infected with R5X4 HIV-1 (HE) and incubated in the presence of test compounds (100 nM). After incubation for 6 h, the cells were washed to remove unadsorbed viral particles and further incubated in the presence of the same concentration of the test compounds for 3 days.
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COA
Plasma concentration-time profiles after single oral administration of TAK-652 to humans.