ancriviroc   Click here for help

GtoPdb Ligand ID: 804

Synonyms: SCH 351125 | SCH-351125 | SCH-C
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Ancriviroc (SCH351125) is an orally available, small molecule antagonist of the C-C chemokine receptor type 5 (CCR5) expressed on T cells [4]. The compound was originally investigated as an anti-HIV therapeutic [4]. SCH351125-induced CCR5 blockade was investigated for action in treating rheumatoid arthritis, but with discouraging clinical trial results [6]. Other CCR5 antagonists (AZD5672 and maraviroc) have also proven ineffective in RA clinical trials [5].

There is some ambiguity in the literature and online databases as to the exact structure of ancriviroc. The structure shown here matches that in the PubChem entry linked to above, and as shown in [4], while other common representations of ancriviroc match CID 5479787.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 72.08
Molecular weight 556.2
XLogP 6.4
No. Lipinski's rules broken 1
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Canonical SMILES CCON=C(c1ccc(cc1)Br)C1CCN(CC1)C1(C)CCN(CC1)C(=O)c1c(C)cc[n+](c1C)[O-]
Isomeric SMILES CCO/N=C(\c1ccc(cc1)Br)/C1CCN(CC1)C1(C)CCN(CC1)C(=O)c1c(C)cc[n+](c1C)[O-]
InChI InChI=1S/C28H37BrN4O3/c1-5-36-30-26(22-6-8-24(29)9-7-22)23-11-15-32(16-12-23)28(4)13-18-31(19-14-28)27(34)25-20(2)10-17-33(35)21(25)3/h6-10,17,23H,5,11-16,18-19H2,1-4H3/b30-26+
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CCR5 Hs Antagonist Antagonist 7.8 – 8.7 pKi - 1-3
pKi 7.8 – 8.7 [1-3]