SML0911

TAK-779

≥98% (HPLC), HIV entry inhibitor, powder

• Synonym(s): N,N-Dimethyl-N-[4-[[[2-(4-methylphenyl)-6,7-dihydro-5H-benzohepten-8-yl]carbonyl]amino]benzyl]tetrahydro-2H-pyran-4-aminium chloride, TAK-799, Takeda 779
• Empirical Formula (Hill Notation): C₃₃H₃₉ClN₂O₂
• CAS Number: 229005-80-5
• Molecular Weight: 531.13
• UNSPSC Code: 51111800
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Product Name: TAK-779, ≥98% (HPLC)
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: H₂O: 3 mg/mL, clear (warmed)
• storage temp.: 2-8°C
• SMILES string: Cl.[N+](C5CCOCC5)(Cc1ccc(cc1)\N=C(/[O-])\C2=Cc3c(ccc(c3)c4ccc(cc4)C)CCC2)(C)C
• InChI: 1S/C33H38N2O2.ClH/c1-24-7-11-27(12-8-24)28-14-13-26-5-4-6-29(22-30(26)21-28)33(36)34-31-15-9-25(10-16-31)23-35(2,3)32-17-19-37-20-18-32;/h7-16,21-22,32H,4-6,17-20,23H2,1-3H3;1H
• InChI key: VDALIBWXVQVFGZ-UHFFFAOYSA-N

Description

Application

TAK-779 has been used to inhibit CC chemokine ligand 5 (CCL5)– C-C chemokine receptor type 5 (CCR5) interaction in vitro in natural killer (NK) cytotoxicity assay.[1] It has also been used as a blocker of CCR5 to study its effects and to evaluate the opening of the Panx-1 channels on peripheral blood mononuclear cells (PBMCs) isolated from human immunodeficiency virus (HIV)-infected individuals.[2]

Biochem/physiol Actions

TAK-779 inhibits human immunodeficiency virus (HIV) entrance by blocking the C-C chemokine receptor type 5 (CCR5). It also impairs the formation of atherosclerotic lesions by preventing T-helper 1 cells from entering the plaque. TAK-779 possesses anti-immunogenic properties. In an arthritis model, it could prevent the inflow of CCR5- and chemokine (C-X-C motif) receptor 3 (CXCR3)-positive T cells into inflamed joints.[3] In mice, TTAK-779 protects the brain from focal cerebral ischemia.[4]

TAK-779 is a potent, dual antagonist at chemokine receptors C-C chemokine receptor type 2 (CCR2) and C-C chemokine receptor type 5 (CCR5) with IC⁵⁰ = 1.4 nM at CCR5 and 2.3 nM at CCR2. Antagonists of both CCR2 and CCR5 such as TAK-779 have been investigated for treatment of viruses, rheumatoid arthritis, multiple sclerosis, and cancer. CCR5 is particularly targeted for anti-HIV therapy, since HIV entry into cells requires chemokine coreceptors CCR5 and C-X-C motif chemokine receptor 4 (CXCR4).

TAK-779 is a potent, dual antagonist at chemokine receptors CCR2 and CCR5.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable