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    Namodenoson

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 2-cl-ib-meca, 163042-96-4, Namodenoson, Cl-ib-meca, Cf-102, Cf102
    Molecular Formula
    C18H18ClIN6O4
    Molecular Weight
    544.7  g/mol
    InChI Key
    IPSYPUKKXMNCNQ-PFHKOEEOSA-N
    FDA UNII
    Z07JR07J6C
    Namodenoson is an orally bioavailable, synthetic, highly selective adenosine A3 receptor (A3AR) agonist with potential antineoplastic activity. Namodenoson selectively binds to and activates the cell surface-expressed A3AR, deregulating Wnt and NF-kB signal transduction pathways downstream, which may result in apoptosis of A3AR-expressing tumor cells. A3AR, a G protein-coupled receptor, is highly expressed on the cell surfaces of various solid tumor cell types, including hepatocellular carcinoma (HCC) cells, and plays an important role in cellular proliferation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3S,4R,5R)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide
    2.1.2 InChI
    InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1
    2.1.3 InChI Key
    IPSYPUKKXMNCNQ-PFHKOEEOSA-N
    2.1.4 Canonical SMILES
    CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O
    2.1.5 Isomeric SMILES
    CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    Z07JR07J6C
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-chloro-n(6)-(3-iodobenzyl)-9-(5-(methylcarbamoyl)-beta-d-ribofuranosyl)adenine

    2. 2-chloro-n(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide

    3. 2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methylcarboxamide

    4. 2-cl-ib-meca

    5. C-ibza-mu

    6. Cf102 Compound

    2.3.2 Depositor-Supplied Synonyms

    1. 2-cl-ib-meca

    2. 163042-96-4

    3. Namodenoson

    4. Cl-ib-meca

    5. Cf-102

    6. Cf102

    7. C-ibza-mu

    8. (2s,3s,4r,5r)-5-(2-chloro-6-((3-iodobenzyl)amino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyltetrahydrofuran-2-carboxamide

    9. Ci-ib-meca

    10. 2-chloro-n(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide

    11. Namodenoson [usan]

    12. 2cl-ib-meca

    13. (2s,3s,4r,5r)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-n-methyloxolane-2-carboxamide

    14. Chembl431733

    15. Z07jr07j6c

    16. 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-beta-d-ribofuranuronamide

    17. Unii-z07jr07j6c

    18. 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-beta-d-ribofuranuronamide

    19. Beta-d-ribofuranuronamide, 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-

    20. Beta-d-ribofuranuronamide, 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-

    21. Cf 102

    22. 2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methylcarboxamide

    23. Namodenoson [inn]

    24. Namodenoson (cf-102)

    25. Namodenoson (usan/inn)

    26. C1-ib-meca

    27. 2-chloro-n(6)-(3-iodobenzyl)-9-(5-(methylcarbamoyl)-beta-d-ribofuranosyl)adenine

    28. Gtpl457

    29. Namodenoson [who-dd]

    30. Mls002153535

    31. Schembl1170028

    32. Bdbm21221

    33. 2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methyluronamide

    34. Cf-102;2-cl-ib-meca

    35. Dtxsid80167504

    36. Hms2235l10

    37. Hms3412i05

    38. Hms3676i05

    39. Cf-102(2-cl-ib-meca)

    40. Ex-a2882

    41. Zinc3995845

    42. Mfcd01861178

    43. Akos022181265

    44. Am84557

    45. Cs-5932

    46. Db12885

    47. Ncgc00025001-02

    48. Ac-27390

    49. Ds-16397

    50. Hy-12365

    51. Smr001230862

    52. Chloro-ib-meca, Solid, >=98% (hplc)

    53. B6597

    54. C3601

    55. S0498

    56. D11128

    57. P10208

    58. A848899

    59. J-009992

    60. Q27076097

    61. 2-chloro-n6-(3-iodobenzyl)adenosine-5-n-methylcarboxamide

    62. (2s,3s,4r,5r)-5-(2-chloro-6-(3-iodobenzylamino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyltetrahydrofuran-2-carboxamide

    63. (2s,3s,4r,5r)-5-(2-chloro-6-{[(3-iodophenyl)methyl]amino}-9h-purin-9-yl)-3,4-dihydroxy-n-methyloxolane-2-carboxamide

    64. (2s,3s,4r,5r)-5-(6-(3-iodobenzylamino)-2-chloro-9h-purin-9-yl)-3,4-dihydroxy-n-methyl-tetrahydrofuran-2-carboxamide

    65. .beta.-d-ribofuranuronamide, 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-

    66. 1-(2-chloro-6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-.beta.-d-ribofuranuronamide

    67. 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-?-d-ribofuranuronamide

    68. 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-1-deoxy-n-methyl-beta-d-ribofuranuronamide;2-chloro-n6-(3-iodobenzyl)adenosine-5'-n-methyluronamide;2-cl-ib-meca;2-cl-ib-meca

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 544.7 g/mol
    Molecular Formula C18H18ClIN6O4
    XLogP31.9
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass544.01228 g/mol
    Monoisotopic Mass544.01228 g/mol
    Topological Polar Surface Area134 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity623
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Purinergic P1 Receptor Agonists

    Compounds that bind to and stimulate PURINERGIC P1 RECEPTORS. (See all compounds classified as Purinergic P1 Receptor Agonists.)