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Maraviroc is an antagonist of chemokine (C-C motif) receptor 5 (CCR5, Ki = 0.24 nM for the rhesus monkey recombinant receptor). It inhibits binding of MIP-1alpha, MIP-1beta, and RANTES to HEK293 cell membranes expressing CCR5 (IC50s = 3.3, 7.2, and 5.2 nM, respectively) and inhibits HIV-1 binding to CCR5 via glycoprotein 120 (gp120) and gp160 (IC50s = 11 and 0.22 nM, respectively). Maraviroc is selective for CCR5 over CCR1, -2, -3, -4, -7, and -8, and chemokine (C-X-C motif) receptor 1 (CXCR1) and CXCR2 in a panel of immunological assays for ligand-induced cell chemotaxis and ligand-receptor binding (IC50s = >10 µM for all). It has antiviral activity against laboratory and clinical isolates of CCR5-tropic (IC50s = 0.1-1.1 nM), but not CXCR4-tropic or dual tropic (IC50s = >10 µM), HIV-1 in isolated human peripheral blood mononuclear cells (PBMCs). Maraviroc prevents infection upon exposure to HIV-1 in humanized RAG-hum mice when administered at a dose of 62 mg/kg.Formal Name: 4,4-difluoro-N-[(1S)-3-[(3-exo)-3-[3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]-cyclohexanecarboxamide. CAS Number: 376348-65-1. Synonyms: UK 427857. Molecular Formula: C29H41F2N5O. Formula Weight: 513.7. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 5 mg/ml, DMSO: 3.3 mg/ml, Ethanol: 25 mg/ml, Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml. SMILES: FC1(F)CCC(C(N[C@H](C2=CC=CC=C2)CCN3[C@H]4C[C@@H](N5C(C(C)C)=NN=C5C)C[C@@H]3CC4)=O)CC1. InChi Code: 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. InChi Key: GSNHKUDZZFZSJB-QYOOZWMWSA-N.
Keywords:
UK 427857, 4,4-difluoro-N-[(1S)-3-[(3-exo)-3-[3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]-cyclohexanecarboxamide
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