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
References
1. Christopoulos A, Changeux JP, Catterall WA, Fabbro D, Burris TP, Cidlowski JA, Olsen RW, Peters JA, Neubig RR, Pin JP et al.. (2014)
International union of basic and clinical pharmacology. XC. multisite pharmacology: recommendations for the nomenclature of receptor allosterism and allosteric ligands.
Pharmacol. Rev., 66 (4): 918-47. [PMID:25026896]
2. Dorr P, Westby M, Dobbs S, Griffin P, Irvine B, Macartney M, Mori J, Rickett G, Smith-Burchnell C, Napier C et al.. (2005)
Maraviroc (UK-427,857), a potent, orally bioavailable, and selective small-molecule inhibitor of chemokine receptor CCR5 with broad-spectrum anti-human immunodeficiency virus type 1 activity.
Antimicrob. Agents Chemother., 49 (11): 4721-32. [PMID:16251317]
3. Mencarelli A, Cipriani S, Francisci D, Santucci L, Baldelli F, Distrutti E, Fiorucci S. (2016)
Highly specific blockade of CCR5 inhibits leukocyte trafficking and reduces mucosal inflammation in murine colitis.
Sci Rep, 6: 30802. [PMID:27492684]
4. Napier C, Sale H, Mosley M, Rickett G, Dorr P, Mansfield R, Holbrook M. (2005)
Molecular cloning and radioligand binding characterization of the chemokine receptor CCR5 from rhesus macaque and human.
Biochem. Pharmacol., 71 (1-2): 163-72. [PMID:16298345]
5. Takeuchi T, Kameda H. (2012)
What is the future of CCR5 antagonists in rheumatoid arthritis?.
Arthritis Res. Ther., 14 (2): 114. [PMID:22494450]