maraviroc   

GtoPdb Ligand ID: 806

Synonyms: Celsentri® | Selzentry® | UK 427857 | UK-427,857
maraviroc is an approved drug (EMA and FDA (2007))
Compound class: Synthetic organic
Comment: Maraviroc is a small molecule antagonist of the C-C chemokine receptor type 5 (CCR5) expressed on T cells.

The stereochemistry of maraviroc as specified by the PDB compound link varies from that specified in our structure and that of CID 3002977.The compound is represented on ChEMBL by CHEMBL1201187.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 63.05
Molecular weight 513.33
XLogP 6.82
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(C1CCC(CC1)(F)F)NC(c1ccccc1)CCN1C2CCC1CC(C2)n1c(C)nnc1C(C)C
Isomeric SMILES O=C(C1CCC(CC1)(F)F)N[C@H](c1ccccc1)CCN1[C@@H]2CC[C@H]1CC(C2)n1c(C)nnc1C(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
InChI Key GSNHKUDZZFZSJB-HLMSNRGBSA-N
No information available.
Summary of Clinical Use
Maraviroc is approved for use in combination antiretroviral treatment of patients infected with CCR5-tropic HIV-1 virus.

Maraviroc-induced CCR5 blockade was investigated for action in treating rheumatoid arthritis, but with discouraging clinical trial results. Other CCR5 antagonists (AZD5672 and ancriviroc) have also proven ineffective in RA clinical trials [5]
Mechanism Of Action and Pharmacodynamic Effects
CCR5 is a co-receptor for HIV-1 and other viruses, allowing these viruses to enter cells. Maraviroc selectively antagonises the interaction between the human CCR5 receptor and HIV-1 envelope glycoprotein gp120. This prevents the CCR5-tropic HIV-1 from entering the cells [2]. Maraviroc has also been shown to inhibit leukocyte trafficking and mucosal inflammation in a mouse colitis model [3], suggesting a CCR5-based interventional strategy with therapeutic potential in inflammatory bowel diseases.
External links