Maraviroc, CCR5 Antagonist

Key facts

CAS number

376348-65-1

Purity

>98%

Form

Solid

form

Molecular weight

513.7 Da

Molecular formula

C₂₉H₄₁F₂N₅O

PubChem

3002977

Nature

Synthetic

Solubility

Soluble in DMSO to 25 mM

Biochemical name

Maraviroc

Biological description

Potent and selective CCR5 antagonist. Blocks binding of MIP-1 alpha (IC₅₀ = 3.3 nM), MIP-1 beta (IC₅₀= 7.2 nM) and RANTES (IC₅₀ = 5.2 nM) to CCR5 in radioligand binding competition assays. Potent anti-HIV activity. Blocks HIV-1 gp120 binding to CCR5 (IC₅₀ = 6.4 nM) preventing cell-cell fusion. Induces macrophage repolarization with anti-tumor effects.

Canonical smiles

CC1=NN=C(N1C2CC3CCC(C2)N3CCC(C4=CC=CC=C4)NC(=O)C5CCC(CC5)(F)F)C(C)C

Isomeric smiles

CC1=NN=C(N1C2C[C@H]3CC[C@@H](C2)N3CC[C@@H](C4=CC=CC=C4)NC(=O)C5CCC(CC5)(F)F)C(C)C

InChi

InChI=1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25?,26-/m0/s1

InChiKey

GSNHKUDZZFZSJB-HLMSNRGBSA-N

IUPAC Name

4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide