maraviroc   Click here for help

GtoPdb Ligand ID: 806

Synonyms: Celsentri® | Selzentry® | UK 427857 | UK-427,857
Approved drug Immunopharmacology Ligand
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.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
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 Click here for help
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 Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)