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Chemistry

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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 Formula	C₉H₁₂N₂O₅S
Molecular Weight	260.27 g/mol
XLogP3	-1.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	260.04669266 g/mol
Monoisotopic Mass	260.04669266 g/mol
Topological Polar Surface Area	154 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	305
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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