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Tiazofurin
Also known as: Tiazofurine, 60084-10-8, Riboxamide, 2-b-d-ribofuranosyl-4-thiazolecarboxamide, Tiazofurinum, Tiazofurina
Molecular Formula
C9H12N2O5S
Molecular Weight
260.27  g/mol
InChI Key
FVRDYQYEVDDKCR-DBRKOABJSA-N
FDA UNII
ULJ82834RE

Tiazofurine has potential clinical use in cancer treatment as it is a potential inhibitor of Inosine- 5-monophosphate (IMP) dehydrogenase.
1 2D Structure

Tiazofurin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
2.1.2 InChI
InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1
2.1.3 InChI Key
FVRDYQYEVDDKCR-DBRKOABJSA-N
2.1.4 Canonical SMILES
C1=C(N=C(S1)C2C(C(C(O2)CO)O)O)C(=O)N
2.1.5 Isomeric SMILES
C1=C(N=C(S1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
2.2 Other Identifiers
2.2.1 UNII
ULJ82834RE
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-beta-d-ribofuranosylthiazole-4-carboxamide

2. 2-ribofuranosylthiazole-4-carboxamide

3. Nsc 286193

4. Riboxamide

5. Tiazofurin, (alpha-d)-isomer

6. Tiazole

2.3.2 Depositor-Supplied Synonyms

1. Tiazofurine

2. 60084-10-8

3. Riboxamide

4. 2-b-d-ribofuranosyl-4-thiazolecarboxamide

5. Tiazofurinum

6. Tiazofurina

7. Tiazofurin [usan]

8. Tcar

9. Nsc-286193

10. Ci-909

11. Tiazofurine (inn)

12. Tiazofurine [inn]

13. Tiazofurin (usan)

14. 2-beta-d-ribofuranosyl-4-thiazolecarboxamide

15. Ulj82834re

16. Chebi:90239

17. 2-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazole-4-carboxamide

18. Tiazofurinum [latin]

19. Tiazofurina [spanish]

20. 2-(beta-d-ribofuranosyl)-4-thiazolecarboxamide

21. (1r)-1,4-anhydro-1-(4-carbamoyl-1,3-thiazol-2-yl)-d-ribitol

22. (1r)-1-[4-(aminocarbonyl)-1,3-thiazol-2-yl]-1,4-anhydro-d-ribitol

23. 2-.beta.-d-ribofuranosyl-4-thiazolecarboxamide

24. Brn 1084555

25. Unii-ulj82834re

26. Cpd-5825

27. 2-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]thiazole-4-carboxamide

28. Tiazofurin [mi]

29. 2-beta-d-ribofuranosylthiazole-4-carboxamide

30. 4-thiazolecarboxamide, 2-beta-d-ribofuranosyl-

31. Schembl4287

32. 2-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide

33. Tiazofurine [who-dd]

34. Dibutylaminehydrochloride

35. Chembl108358

36. Dtxsid00208827

37. Zinc4217560

38. Bdbm50368057

39. Mfcd00866494

40. Db13243

41. Bs-17271

42. Hy-114570

43. Cs-0063433

44. C22196

45. D06130

46. W18798

47. Q7800305

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 260.27 g/mol
Molecular Formula C9H12N2O5S
XLogP3-1.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass260.04669266 g/mol
Monoisotopic Mass260.04669266 g/mol
Topological Polar Surface Area154 Ų
Heavy Atom Count17
Formal Charge0
Complexity305
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

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


4.2 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XX - Other antineoplastic agents

L01XX18 - Tiazofurine


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