Triapine

Synopsis, Chemistry

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Also known as: 143621-35-6, 236392-56-6, 200933-27-3, 3-ap, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, Ocx 191

Molecular Formula

C₇H₉N₅S

Molecular Weight

195.25 g/mol

InChI Key

XMYKNCNAZKMVQN-NYYWCZLTSA-N

FDA UNII

U4XIL4091C

Triapine is a synthetic heterocyclic carboxaldehyde thiosemicarbazone with potential antineoplastic activity. Triapine inhibits the enzyme ribonucleotide reductase, resulting in the inhibition of the conversion of ribonucleoside diphosphates to deoxyribonucleotides necessary for DNA synthesis. This agent has been shown to inhibit tumor growth in vitro. (NCI04)

1 2D Structure

Triapine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(E)-(3-aminopyridin-2-yl)methylideneamino]thiourea

2.1.2 InChI

InChI=1S/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+

2.1.3 InChI Key

XMYKNCNAZKMVQN-NYYWCZLTSA-N

2.1.4 Canonical SMILES

C1=CC(=C(N=C1)C=NNC(=S)N)N

2.1.5 Isomeric SMILES

C1=CC(=C(N=C1)/C=N/NC(=S)N)N

2.2 Other Identifiers

2.2.1 UNII

U4XIL4091C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-aminopyridine-2-carboxaldehyde Thiosemicarbazone

2. 3-apct

3. Nsc 663249

4. Pan 811

5. Pan-811

6. Pan811

2.3.2 Depositor-Supplied Synonyms

1. 143621-35-6

2. 236392-56-6

3. 200933-27-3

4. 3-ap

5. 3-aminopyridine-2-carboxaldehyde Thiosemicarbazone

6. Ocx 191

7. 2-((3-aminopyridin-2-yl)methylene)hydrazinecarbothioamide

8. Pan-811

9. Nsc-663249

10. U4xil4091c

11. Ocx-191

12. Ocx-0191

13. [(e)-(3-aminopyridin-2-yl)methylideneamino]thiourea

14. 3-apct

15. Hydrazinecarbothioamide, 2-((3-amino-2-pyridinyl)methylene)-

16. 3-aminopyridine-2-carbaldehyde-thiosemicarbazone

17. Pan 811

18. Hydrazinecarbothioamide, 2-[(3-amino-2-pyridinyl)methylene]-, (e)-

19. Nsc 663249

20. Pan811

21. Unii-u4xil4091c

22. 2-[(3-amino-2-pyridinyl)methylene]hydrazinecarbothioamide

23. [(e)-(3-amino-2-pyridyl)methyleneamino]thiourea

24. Schembl29370

25. Chembl231616

26. Ocx 191 [who-dd]

27. Dtxsid90893923

28. Ex-a1926

29. Zinc8665373

30. Bdbm50198892

31. Mfcd00924747

32. Nsc759096

33. S7470

34. Akos006273720

35. Ccg-266543

36. Db11940

37. Nsc-759096

38. Ac-36254

39. As-16679

40. Hy-10082

41. A14306

42. 392t566

43. A857776

44. A879844

45. A936642

46. 3-aminopyridine-2-carboxaldehyde- Thiosemicarbazone

47. Hydrazinecarbothioamide,2-(3-amino-2-pyridinyl)methylene-

48. 2-((3-aminopyridin-2-yl)methylene)hydrazine-1-carbothioamide

49. (e)-2-((3-aminopyridin-2-yl)methylene)hydrazine-1-carbothioamide

2.4 Create Date

2006-10-24

3 Chemical and Physical Properties

Molecular Formula	C₇H₉N₅S
Molecular Weight	195.25 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	195.05786648 g/mol
Monoisotopic Mass	195.05786648 g/mol
Topological Polar Surface Area	121 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	205
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1