Apaziquone

Synopsis, Chemistry

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Also known as: 114560-48-4, Eoquin, Qapzola, Eo-9, Nor-701, Nsc-382459

Molecular Formula

C₁₅H₁₆N₂O₄

Molecular Weight

288.30 g/mol

InChI Key

MXPOCMVWFLDDLZ-NSCUHMNNSA-N

FDA UNII

H464ZO600O

Apaziquone is an indolequinone bioreductive prodrug and analog of mitomycin C with potential antineoplastic and radiosensitization activities. Apaziquone is converted to active metabolites in hypoxic cells by intracellular reductases, which are present in greater amounts in hypoxic tumor cells. The active metabolites alkylate DNA, resulting in apoptotic cell death. This agent displays selectivity activity towards both hypoxic solid tumors, which exhibits higher expression of cytochrome P450 reductase, and well-oxygenated malignant cells that overexpress the bioreductive enzyme NQO1 (NAD(P)H: quinone oxidoreductase). Apaziquone may selectively sensitize hypoxic tumor cells to radiocytotoxicity.

1 2D Structure

Apaziquone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(E)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione

2.1.2 InChI

InChI=1S/C15H16N2O4/c1-16-10(3-2-6-18)9(8-19)13-14(16)12(20)7-11(15(13)21)17-4-5-17/h2-3,7,18-19H,4-6,8H2,1H3/b3-2+

2.1.3 InChI Key

MXPOCMVWFLDDLZ-NSCUHMNNSA-N

2.1.4 Canonical SMILES

CN1C(=C(C2=C1C(=O)C=C(C2=O)N3CC3)CO)C=CCO

2.1.5 Isomeric SMILES

CN1C(=C(C2=C1C(=O)C=C(C2=O)N3CC3)CO)/C=C/CO

2.2 Other Identifiers

2.2.1 UNII

H464ZO600O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-hydroxymethyl-5-aziridinyl-1-methyl-2-(1h-indole-4,7-dione)prop-beta-en-alpha-ol

2. 5-(azridin-1-yl)-3-(hydroxymethyl)-2-((1e)-3-hydroxyprop-1-enyl)-methyl-1h-indole-4,7-dione

3. E 09

4. E-09

5. Eo 9

6. Eo-9

7. Eo9

8. Nsc 382,459

9. Nsc 382459

10. Nsc-382459

11. Qapzola

2.3.2 Depositor-Supplied Synonyms

1. 114560-48-4

2. Eoquin

3. Qapzola

4. Eo-9

5. Nor-701

6. Nsc-382459

7. 5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(e)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione

8. E-85/053

9. Eo9

10. 141304-51-0

11. 5-(azridin-1-yl)-3-(hydroxymethyl)-2-((1e)-3-hydroxyprop-1-enyl)-methyl-1h-indole-4,7-dione

12. Apaziquonum

13. H464zo600o

14. Nsc-382456

15. Neoquin

16. Eo 9 (pharmaceutical)

17. Apaziquone [usan:inn]

18. Apaziquonum [inn-latin]

19. 1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-((1e)-3-hydroxy-1-propenyl)-1-methyl-

20. E09

21. E 09

22. 5-aziridin-1-yl-3-hydroxymethyl-2-((e)-3-hydroxy-propenyl)-1-methyl-1h-indole-4,7-dione

23. Nsc 382459

24. Eoquin (tn)

25. E-09

26. Apaziquone (usan/inn)

27. Nsc 382456

28. Unii-h464zo600o

29. 1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-

30. Apaziquone [usan]

31. (e)-5-(1-azirinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1h-indole-4,7-dione

32. Apaziquone [mi]

33. Apaziquone [inn]

34. 1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-, (e)-

35. Chembl73822

36. Schembl367964

37. Schembl367965

38. E-85/050

39. Antineoplastic-382459

40. Dtxsid90869587

41. Chebi:177558

42. Zinc1536777

43. N1,n6-diethyl-3-methylhexanediamide

44. Nsc382459

45. Bcp9000309

46. Db12593

47. Cs-0006128

48. D02965

49. Q4779259

50. 1h-indole-4, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-

51. 5-(aziridin-1-yl)-3-(hydroxymethyl)-2-(3-hydroxyprop-1-enyl)-1-methylindole-4,7-dione

52. (e)-5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1h-indole-4,7-dione

53. 5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-1h-indole-4,7-dione

54. 5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-1h-indole-4,7-dione;

2.4 Create Date

2005-09-08

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₆N₂O₄
Molecular Weight	288.30 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	288.11100700 g/mol
Monoisotopic Mass	288.11100700 g/mol
Topological Polar Surface Area	82.5 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	524
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