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Technical details about Bisantrene, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. 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

2D Structure

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 Weight 398.5 g/mol
Molecular Formula C22H22N8
XLogP31.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area97.6
Heavy Atom Count30
Formal Charge0
Complexity630
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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