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Tirapazamine

Tirapazamine

Synopsis, Chemistry

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Also known as: 27314-97-2, 3-aminobenzo[e][1,2,4]triazine 1,4-dioxide, 1,2,4-benzotriazin-3-amine, 1,4-dioxide, Tirazone, 3-amino-1,2,4-benzotriazine 1,4-dioxide, Win-59075

Molecular Formula

C₇H₆N₄O₂

Molecular Weight

178.15 g/mol

InChI Key

ORYDPOVDJJZGHQ-UHFFFAOYSA-N

FDA UNII

1UD32YR59G

A triazine derivative that introduces breaks into DNA strands in hypoxic cells, sensitizing tumor cells to the cytotoxic activity of other drugs and radiation.

1 2D Structure

Tirapazamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,4-dioxido-1,2,4-benzotriazine-1,4-diium-3-amine

2.1.2 InChI

InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)

2.1.3 InChI Key

ORYDPOVDJJZGHQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C2C(=C1)[N+](=C(N=[N+]2[O-])N)[O-]

2.2 Other Identifiers

2.2.1 UNII

1UD32YR59G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-amino-1,2,4-benzotriazine-1,4-dioxide

2. Nsc 130181

3. Sr 4233

4. Sr-4233

5. Sr4233

6. Tirazone

7. Win 59075

8. Win-59075

9. Win59075

2.3.2 Depositor-Supplied Synonyms

1. 27314-97-2

2. 3-aminobenzo[e][1,2,4]triazine 1,4-dioxide

3. 1,2,4-benzotriazin-3-amine, 1,4-dioxide

4. Tirazone

5. 3-amino-1,2,4-benzotriazine 1,4-dioxide

6. Win-59075

7. Win 59075

8. Sr 4233

9. Sr-4233

10. Chebi:78887

11. 1,2,4-benzotriazin-3-amine,1,4-dioxide

12. Sr-259075

13. Nsc-130181

14. Sr259075

15. 1ud32yr59g

16. Sr259075;sr4233;win59075

17. Tirapazamine [usan:inn]

18. Nsc 130181

19. Brn 0179322

20. Unii-1ud32yr59g

21. Win59075

22. 1,2,4-benzotriazin-3-amine 1,4-dioxide

23. Sr4233

24. 4-hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine

25. Tirapazamine [mi]

26. Tirapazamine (usan/inn)

27. Tirapazamine [inn]

28. Tirapazamine [usan]

29. Schembl4048

30. Schembl4049

31. 1,2,4-benzotriazine, 3-amino-, 1,4-dioxide

32. Tirapazamine [mart.]

33. 4-26-00-01120 (beilstein Handbook Reference)

34. Chembl50882

35. Schembl872285

36. Tirapazamine [who-dd]

37. Tirapazamine, >=98% (hplc)

38. Amy38675

39. Bcp03663

40. Ex-a2967

41. Zinc1607808

42. Bdbm50226806

43. Mfcd00132954

44. Akos006271584

45. Akos037645846

46. Db04858

47. Ncgc00390788-04

48. Ac-31305

49. As-64112

50. Hy-13767

51. Bcp0726000167

52. Ft-0661586

53. T3823

54. 3-aminobenzo[e][1,2,4]triazine1,4-dioxide

55. D06167

56. T72208

57. J-016728

58. Q3529346

59. 1,4-dioxido-1,2,4-benzotriazine-1,4-diium-3-amine

60. 3-amino-1,2,4-benzotriazine-1,4-diium-1,4-bis(olate)

61. 4-hydroxy-3-imino-3,4-dihydro-1,2,4-benzotriazin-1-ium-1-olate

2.4 Create Date

2019-01-15

3 Chemical and Physical Properties

Molecular Formula	C₇H₆N₄O₂
Molecular Weight	178.15 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	0
Exact Mass	178.04907545 g/mol
Monoisotopic Mass	178.04907545 g/mol
Topological Polar Surface Area	89.8 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	191
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 Drug Indication

For the treatment of head and neck cancer.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tirapazamine is a anticancer drug that is inactive in normal tissues that are well oxygenated, but becomes active at the low oxygen levels found in solid tumors. As a result, the drug kills these poorly oxygenated or hypoxic cells while limiting toxicity in normal tissue. Tirapazamine may prove highly effective when used in combination with standard anticancer therapy, as these hypoxic cells are characteristically resistant to radiation and common anticancer agents.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

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

Radiation-Sensitizing Agents

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)

5.3 Mechanism of Action

Extensive preclinical testing has established that the mechanism for the selective toxicity towards hypoxic cells is the result of a one-electron reduction of the parent molecule to a free radical species that interacts with DNA to produce single- and double-strand breaks and lethal chromosome aberrations. It has also shown activity when combined with fractionated irradiation and when combined with some chemotherapy agents, particularly cisplatin and carboplatin.