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6-Thio-2-Deoxyguanosine

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Chemistry

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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

6-Thio-2-Deoxyguanosine

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 Formula	C₁₀H₁₃N₅O₃S
Molecular Weight	283.31 g/mol
XLogP3	-0.8
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	283.07391047 g/mol
Monoisotopic Mass	283.07391047 g/mol
Topological Polar Surface Area	150 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	420
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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)

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