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    6-Thio-2-Deoxyguanosine

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: 789-61-7, 6-thio-dg, Tgdr, Thioguanine deoxyriboside, 6-thio-2'-deoxyguanosine, 2'-deoxy-6-thioguanosine
    Molecular Formula
    C10H13N5O3S
    Molecular Weight
    283.31  g/mol
    InChI Key
    SCVJRXQHFJXZFZ-KVQBGUIXSA-N
    FDA UNII
    KR0RFB46DF
    Beta-Thioguanine Deoxyriboside is a thiopurine nucleoside derivative with antineoplastic activity. After conversion to the triphosphate, beta-thioguanine deoxyriboside is incorporated into DNA, resulting in inhibition of DNA replication. This agent is cytotoxic against leukemia cell lines and has demonstrated some activity against leukemia cells in vivo. Beta-thioguanine deoxyriboside demonstrates antineoplastic activity against 6-thioguanine-resistant tumor cells. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
    2.1.2 InChI
    InChI=1S/C10H13N5O3S/c11-10-13-8-7(9(19)14-10)12-3-15(8)6-1-4(17)5(2-16)18-6/h3-6,16-17H,1-2H2,(H3,11,13,14,19)/t4-,5+,6+/m0/s1
    2.1.3 InChI Key
    SCVJRXQHFJXZFZ-KVQBGUIXSA-N
    2.1.4 Canonical SMILES
    C1C(C(OC1N2C=NC3=C2NC(=NC3=S)N)CO)O
    2.1.5 Isomeric SMILES
    C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2NC(=NC3=S)N)CO)O
    2.2 Other Identifiers
    2.2.1 UNII
    KR0RFB46DF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2'-deoxy-6-thioguanosine

    2. Beta-2'-deoxythioguanosine

    3. Beta-2'-deoxythioguanosine Mono-hydrate

    4. Beta-thioguanine Deoxyriboside

    2.3.2 Depositor-Supplied Synonyms

    1. 789-61-7

    2. 6-thio-dg

    3. Tgdr

    4. Thioguanine Deoxyriboside

    5. 6-thio-2'-deoxyguanosine

    6. 2'-deoxy-6-thioguanosine

    7. Beta-2'-deoxythioguanosine

    8. 2'-desoxy-6-thioguanosine

    9. 6-mercaptoguaninedeoxyriboside

    10. Kr0rfb46df

    11. Beta-thioguanidine Deoxyriboside

    12. Beta-thioguanine Deoxyriboside

    13. 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione

    14. Beta-2'-deoxy-6-thioguanosine Monohydrate

    15. Guanosine, 2'-deoxy-6-thio-

    16. B-tgdr

    17. 2'deoxy-6-thioguanosine

    18. Thio

    19. 2'-deoxy-6-thio Guanosine

    20. Beta-2'-deoxythiol Guanosine

    21. Ccris 195

    22. Nsc71261

    23. Nsc-71261

    24. Thioguanine Deoxyriboside (van)

    25. Thiodeoxyguanosine

    26. Hsdb 7074

    27. Beta-tgdr

    28. 2-amino-9-(2-deoxy-beta-d-erythro-pentofuranosyl)-1,9-dihydro-6h-purine-6-thione

    29. Nci-c01581

    30. Thioguanine 9betad-2'-deoxyriboside

    31. Brn 1224220

    32. 6-thio-dg;

    33. A-tgdr

    34. Unii-kr0rfb46df

    35. Schembl531274

    36. Beta-thioguanosine Deoxyriboside

    37. Schembl9634767

    38. Chembl3250476

    39. Dtxsid4021345

    40. Mfcd00672275

    41. S7757

    42. Zinc17969618

    43. Ccg-267279

    44. Ac-32335

    45. Hy-18762

    46. Cs-0014289

    47. 6-thio-2 Inverted Exclamation Marka-deoxyguanosine

    48. 2-amino-9-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-6-mercaptopurine

    49. 2-amino-9-(2-deoxy-.beta.-d-erythropentofuranosyl)-9h-purine-6(1h)-thione

    50. 9h-purine-6(1h)-thione, 2-amino-9-(2-deoxy-beta-d-erythro-pentofuranosyl)-

    51. 2-amino-9-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-purine-6(9h)-thione

    52. 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1h-purine-6-thione

    53. 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1h-purine-6-thione

    54. 30241-92-0

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 283.31 g/mol
    Molecular Formula C10H13N5O3S
    XLogP3-0.8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass283.07391047 g/mol
    Monoisotopic Mass283.07391047 g/mol
    Topological Polar Surface Area150 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity420
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    STUDIES SUGGEST THAT BETA-TGDR IS A LATENT FORM OF TG. SINCE RESISTANCE TO ANTILEUKEMIC AGENT 6-THIOGUANINE INEVITABLY DEVELOPS IN ANIMAL TUMORS, THIS NEW AGENT BETA-TGDR IS OF POTENTIAL CLINICAL USE.

    LU K ET AL; PHARMACOKINETICS AND METABOLISM OF BETA-2'-DEOXYTHIOGUANOSINE AND 6-THIOGUANINE IN MAN; CANCER CHEMOTHER PHARMACOL 8 (1): 119-23 (1982)

    5 Pharmacology and Biochemistry
    5.1 Metabolism/Metabolites

    THE PHARMACOKINETICS OF RADIOLABELED 6-THIOGUANINE (TG) WERE COMPARED WITH THAT OF BETA-2'-DEOXYTHIOGUANOSINE (BETA-TGDR) AFTER IV ADMIN. URINARY EXCRETION OF THE RADIOLABEL WAS 75% OF THE DOSE 24 HR AFTER ADMIN. BOTH THIOPURINES WERE RAPIDLY & EXTENSIVELY DEGRADED & EXCRETED AS 6-THIOXANTHINE, INORGANIC SULFATE, S-METHYL-6-THIOXANTHINE, & 6-THIOURIC ACID IN ADDITION TO OTHER PRODUCTS. SMALL AMOUNTS OF UNCHANGED DRUG WERE ALSO EXCRETED. STUDIES SUGGEST THAT BETA-TGDR IS A LATENT FORM OF TG. SINCE RESISTANCE TO ANTILEUKEMIC AGENT 6-THIOGUANINE INEVITABLY DEVELOPS IN ANIMAL TUMORS, THIS NEW AGENT BETA-TGDR IS OF POTENTIAL CLINICAL USE.

    LU K ET AL; PHARMACOKINETICS AND METABOLISM OF BETA-2'-DEOXYTHIOGUANOSINE AND 6-THIOGUANINE IN MAN; CANCER CHEMOTHER PHARMACOL 8 (1): 119-23 (1982)