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Also known as: 78186-34-2, Bisantrene [inn], Bisantrenum [inn-latin], Bisantreno [inn-spanish], Nsc 337766, Bisantrene hydrochloride

Molecular Formula

C₂₂H₂₂N₈

Molecular Weight

398.5 g/mol

InChI Key

NJSMWLQOCQIOPE-OCHFTUDZSA-N

FDA UNII

39C34M111K

Bisantrene is an anthracenyl bishydrazone with antineoplastic activity. Bisantrene intercalates with and disrupts the configuration of DNA, resulting in DNA single-strand breaks, DNA-protein crosslinking, and inhibition of DNA replication. This agent is similar to doxorubicin in activity, but unlike doxorubicin, does not exhibit cardiotoxicity. (NCI04)

1 2D Structure

Bisantrene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(E)-[10-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1H-imidazol-2-amine

2.1.2 InChI

InChI=1S/C22H22N8/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30)/b27-13+,28-14+

2.1.3 InChI Key

NJSMWLQOCQIOPE-OCHFTUDZSA-N

2.1.4 Canonical SMILES

C1CN=C(N1)NN=CC2=C3C=CC=CC3=C(C4=CC=CC=C42)C=NNC5=NCCN5

2.1.5 Isomeric SMILES

C1NC(=NC1)N/N=C/C2=C3C(=C(C4=CC=CC=C24)/C=N/NC5=NCCN5)C=CC=C3

2.2 Other Identifiers

2.2.1 UNII

39C34M111K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9,10-anthracenedicarboxaldehyde Bis(4,5-dihydro-1h-imidazol-2-yl)hydrazone

2. Bisantrene Dihydrochloride

3. Cl 216942

4. Cl216,942

5. Nsc 337766

2.3.2 Depositor-Supplied Synonyms

1. 78186-34-2

2. Bisantrene [inn]

3. Bisantrenum [inn-latin]

4. Bisantreno [inn-spanish]

5. Nsc 337766

6. Bisantrene Hydrochloride

7. Brn 0966309

8. Bisantrenum

9. Cl 216942

10. Chembl25336

11. Unii-39c34m111k

12. 39c34m111k

13. Bisantrene Hcl

14. N-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine

15. 9,10-anthracendicarbaldehyde Bis(2-imidazolin-2-ylhydrazon)

16. 9,10-bis((2-(4,5-dihydro-1h-imidazol-2-yl)hydrazono)methyl)anthracene

17. 9,10-anthracenedicarboxaldehyde, Bis((4,5-dihydro-1h-imidazol-2-yl)hydrazone)

18. Nsc-337766

19. 9,10-anthracenedicarboxaldehyde Bis(2-imidazolin-2-ylhydrazone)

20. 9,10-bis(2-(4,5-dihydro-1h-imidazol-2-yl)hydrazono)methyl)anthracene

21. C22h22n8.2clh

22. C22-h22-n8.2cl-h

23. Nsc337766

24. 71439-68-4

25. 9,10-anthracenedicarboxaldehyde, Bis((4,5-dihydro-1h-imidazol-2-yl)hydrazone)-

26. Cl216942

27. Bisantrene [mi]

28. Cl216,942

29. 9,10-anthracenedicarboxaldehyde, Bis(4,5-dihydro-1h-imidazol-2-yl Hydrazone),dihydrochloride

30. Bisantrene [who-dd]

31. Schembl8906393

32. 9,10-anthracenedicarboxaldehyde Bis[(4,5-dihydro-1h-imidazol-2-yl)hydrazone]

33. 9,10-bis((e)-(2-(4,5-dihydro-1h-imidazol-2-yl)hydrazono)methyl)anthracene

34. Ex-a2382

35. Bdbm50060768

36. Ccg-35603

37. 9,10-anthracenedicarboxaldehyde Bis(4,5-dihydro-1h-imidazol-2-yl)hydrazone

38. Cs-6132

39. Ac-35847

40. As-75775

41. Ls-20289

42. N-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazono)methyl]-9-anthryl]methyleneamino]-4,5-dihydro-1h-imidazol-2-amine

43. Hy-100875

44. Brd-k64298650-300-01-5

45. 9,10-anthracenedicarboxaldehyde Bis(2-imidazolin-2-yl-hydrazone)

46. 9,10-anthracenedicarbaldehyde Bis(4,5-dihydro-1h-imidazol-2-ylhydrazone)

47. Anthracene-9,10 Bis-carbaldehyde 4,5-dihydro-1h-imidazol-2-ylhydrazone

48. 9,10-anthracenedicarboxaldehyde Bis[(4,5-dihydro-1h-imidazol-2yl)hydrazone)

49. 9,10-anthracenedicarboxaldehyde, Bis(4,5-dihydro-1h-imidazol-2-ylhydrazone),dihydrochloride

50. N-anthracen-9-yl Methylene N''-[(bis)4,5-dihydro-1h-imidazole-2-yl)-hydrazine

51. N-anthracen-bis-9,10-ylmethylene-n''-(4,5-dihydro-1h-imidazol-2-yl)-hydrazine(bisantrene)

52. 10-imino(4,5-dihydro-1h-2-imidazolamine)methyl-9-anthrylmethan-(4,5-dihydro-1h-2-imidazolamine)imine

53. X N-4,5-dihydro-1h-2-imidazolamine-10-iminomethyl-9-anthrylmethanimine-4,5-dihydro-1h-2-imidazolamine (bisantrene)

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₂N₈
Molecular Weight	398.5 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	97.6
Heavy Atom Count	30
Formal Charge	0
Complexity	630
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

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