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    Vicriviroc

    INTERMEDIATES

    PharmaCompass
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    2D Structure
    Also known as: Sch-d, 306296-47-9, Sch-417690, Vicriviroc [inn], Sch 417690, Sch-d690
    Molecular Formula
    C28H38F3N5O2
    Molecular Weight
    533.6  g/mol
    InChI Key
    CNPVJJQCETWNEU-CYFREDJKSA-N
    FDA UNII
    TL515DW4QS
    Vicriviroc is a piperazine-based CCR5 receptor antagonist with activity against human immunodeficiency virus. Vicriviroc is designed to bind to CCR5 and inhibit the entry of HIV into CD4 cells.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4,6-dimethylpyrimidin-5-yl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methylpiperazin-1-yl]-4-methylpiperidin-1-yl]methanone
    2.1.2 InChI
    InChI=1S/C28H38F3N5O2/c1-19-16-35(14-15-36(19)24(17-38-5)22-6-8-23(9-7-22)28(29,30)31)27(4)10-12-34(13-11-27)26(37)25-20(2)32-18-33-21(25)3/h6-9,18-19,24H,10-17H2,1-5H3/t19-,24-/m0/s1
    2.1.3 InChI Key
    CNPVJJQCETWNEU-CYFREDJKSA-N
    2.1.4 Canonical SMILES
    CC1CN(CCN1C(COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
    2.1.5 Isomeric SMILES
    C[C@H]1CN(CCN1[C@@H](COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    TL515DW4QS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-((4,6-dimethyl-5-pyrimidinyl)carbonyl)-4-(4-(2-methoxy-4-(trifluoromethyl)phenyl)ethyl-3-methyl-1-piperazinyl)-4-methylpiperidine

    2. Sch 417690

    3. Sch-417690

    4. Sch417690

    2.3.2 Depositor-Supplied Synonyms

    1. Sch-d

    2. 306296-47-9

    3. Sch-417690

    4. Vicriviroc [inn]

    5. Sch 417690

    6. Sch-d690

    7. (4,6-dimethylpyrimidin-5-yl)-[4-[(3s)-4-[(1r)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methylpiperazin-1-yl]-4-methylpiperidin-1-yl]methanone

    8. Mk-7690

    9. Tl515dw4qs

    10. Chembl82301

    11. Sch-417690 Free Base

    12. Mk-4176

    13. Sch417690

    14. Sch-d Compound

    15. Schd

    16. (4,6-dimethylpyrimidin-5-yl)(4-((s)-4-((r)-2-methoxy-1-(4-(trifluoromethyl)phenyl)ethyl)-3-methylpiperazin-1-yl)-4-methylpiperidin-1-yl)methanone

    17. (4,6-dimethylpyrimidin-5-yl)-[4-[(3s)-4-[(1r)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-piperazin-1-yl]-4-methyl-1-piperidyl]methanone

    18. Vcv

    19. Sch-d (old Rn)

    20. Pro 140 & Vicrivirac

    21. Unii-tl515dw4qs

    22. Vicriviroc (sch-417690)

    23. Sch-ds

    24. Starbld0032646

    25. Vicriviroc [mi]

    26. Ncgc00182549-01

    27. Vicriviroc [who-dd]

    28. Mk-4176 Intravaginal Ring

    29. Gtpl807

    30. 1-((4,6-dimethyl-5-pyrimidinyl)carbonyl)-4-(4-(2-methoxy-4-(trifluoromethyl)phenyl)ethyl-3-methyl-1-piperazinyl)-4-methylpiperidine

    31. Schembl118885

    32. Chebi:94843

    33. Mk-4176 Ivr

    34. Dtxsid40897719

    35. Bdbm50145685

    36. Zinc22010579

    37. Db06652

    38. 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-[4-{2-methoxy-1(r)-4-(trifluoromethyl)-phenyl}ethyl-3(s)-methyl-1-piperazinyl]-4-methylpiperidine

    39. 394730-30-4

    40. Pro 140 (anti-ccr5 Monoclonal Antibody) & 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-[4-{2-methoxy-1(r)-4-(trifluoromethyl)-phenyl}ethyl-3(s)-methyl-1-piperazinyl]-4-methylpiperidine

    41. Ab01274747-01

    42. Q3557001

    43. (4,6-dimethyl-pyrimidin-5-yl)-(4-{(s)-4-[(r)-2-methoxy-1-(4-trifluoromethyl-phenyl)-ethyl]-3-methyl-piperazin-1-yl}-4-methyl-piperidin-1-yl)-methanone

    44. 5-((4-((3s)-4-((1r)-2-methoxy-1-(4-(trifluoromethyl)phenyl)ethyl)-3-methylpiperazin-1-yl)-4-methylpiperidin-1-yl)carbonyl)-4,6-dimethylpyrimidine

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 533.6 g/mol
    Molecular Formula C28H38F3N5O2
    XLogP33.7
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count6
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area61.8
    Heavy Atom Count38
    Formal Charge0
    Complexity773
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in HIV infection and viral infection.

    5 Pharmacology and Biochemistry
    5.1 Metabolism/Metabolites

    Metabolised primarily by the CYP3A4 system

    Vicriviroc has known human metabolites that include N-Desalkylvicriviroc, O-Desmethylvicriviroc, and Vicriviroc N-oxide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.2 Mechanism of Action

    Vicriviroc is a once daily oral inhibitor of CCR5. It noncompetitively binds to a hydrophobic pocket between transmembrance helices by the extracellular side of CCR5. This allosteric antagonism causes a conformational change in the protein preventing binding of gp120 to CCR5. This prevents the entry of HIV into the cell.