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Synopsis

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Chemistry

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Also known as: 539-21-9, Faringosept, Ambazon, Anginon, Primal, Ambazona

Molecular Formula

C₈H₁₁N₇S

Molecular Weight

237.29 g/mol

InChI Key

ANZIOUQAFBXNHU-UHFFFAOYSA-N

FDA UNII

BYK4592A3Q

Ambazone is an antiseptic agent with potential antibacterial and antileukemic activity. Although the exact mechanism of action remains to be fully elucidated, ambazone appears to interfere with the membrane-bound nucleotide system by increasing the intracellular concentration of cAMP in leukemia cells and macrophages, which potentially contributes to this agent's antineoplastic activity. Furthermore, this agent's affinity for various cellular targets, i.e. membranes, nucleic acids and proteins, may contribute to the overall antibacterial effect.

1 2D Structure

Ambazone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[2-(diaminomethylidene)hydrazinyl]phenyl]iminothiourea

2.1.2 InChI

InChI=1S/C8H11N7S/c9-7(10)14-12-5-1-3-6(4-2-5)13-15-8(11)16/h1-4,12H,(H2,11,16)(H4,9,10,14)

2.1.3 InChI Key

ANZIOUQAFBXNHU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1NN=C(N)N)N=NC(=S)N

2.2 Other Identifiers

2.2.1 UNII

BYK4592A3Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,4-benzoquinone Guanylhydrazone Thiosemicarbazone

2. 1,4-benzoquinone Guanylhydrazone Thiosemicarbazone Monohydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 539-21-9

2. Faringosept

3. Ambazon

4. Anginon

5. Primal

6. Ambazona

7. Ambazone [inn:ban:dcf]

8. Ambazone (inn)

9. Mls001240207

10. Inversal

11. Ivertol

12. 1,4-benzoquinone Guanylhydrazone Thiosemicarbazone

13. [4-[2-(diaminomethylidene)hydrazinyl]phenyl]iminothiourea

14. Byk4592a3q

15. Guanothiazon

16. ((4-oxo-2,5-cyclohexadien-1-ylidene)amino)guanidine Thiosemicarbazone

17. Ncgc00164514-01

18. Ambazonum

19. Promassol

20. Smr000674566

21. Ambazone [inn]

22. Ambazonum [inn-latin]

23. Ambazona [inn-spanish]

24. Hydrazinecarbothioamide, 2-(4-((aminoiminomethyl)hydrazono)-2,5-cyclohexadien-1-ylidene)-

25. Ccris 1926

26. Benzoquinone Guanylhydrazone Thiosemicarbazone

27. Hydrazinecarbothioamide, 2-[4-[(aminoiminomethyl)hydrazono]-2,5-cyclohexadien-1-ylidene]-

28. P-benzoquinone Amidinohydrazone Thiosemicarbazone

29. Dc 0572

30. Einecs 208-713-0

31. Unii-byk4592a3q

32. Faringosept (tn)

33. 1-amidinohydrazono-4-thiosemicarbazono-2,5-cyclohexadiene

34. 4-amidinohydrazono-2,5-cyclohexadien-1-on-thiosemicarbazon

35. Ambazone [mi]

36. P-benzoquinoneamidinohydrazonethiosemicarbazone

37. Ambazone [mart.]

38. Ambazone [who-dd]

39. Dsstox_cid_26407

40. Dsstox_rid_81587

41. Dsstox_gsid_46407

42. Schembl457920

43. Schembl1649608

44. Chembl1414870

45. Chembl2103762

46. Chembl3198213

47. Dtxsid3046407

48. Schembl11887782

49. Bdbm53352

50. Cid_1549158

51. Chebi:134962

52. Hms2231l21

53. Zinc1550965

54. Tox21_112149

55. Stl200147

56. Akos000622836

57. Akos002161802

58. Akos005197779

59. Guanidine, ((4-oxo-2,5-cyclohexadien-1-ylidene)amino)-, Thiosemicarbazone

60. Db13697

61. Ncgc00164514-02

62. Cas-539-21-9

63. Ft-0661544

64. D07376

65. 539a219

66. Q414317

67. Sr-01000799157

68. Sr-01000799157-2

69. [4-(2-(diaminomethylidene)hydrazino)phenyl]iminothiourea

70. [4-[n''-(diaminomethylene)hydrazino]phenyl]iminothiourea

71. [(4-{[(diaminomethylidene)amino]amino}phenyl)imino]thiourea

72. 1-[4-[2-[bis(azanyl)methylidene]hydrazinyl]phenyl]iminothiourea

73. {[4-(carbamimidamidoimino)cyclohexa-2,5-dien-1-ylidene]amino}thiourea

74. (2e)-2-{(4e)-4-[(aminocarbonothioyl)hydrazono]cyclohexa-2,5-dien-1-ylidene}hydrazinecarboximidamide

75. (2z)-2-[(4z)-4-(2-carbamimidoylhydrazinylidene)cyclohexa-2,5-dien-1-ylidene]hydrazinecarbothioamide

76. Hydrazinecarbothioamide, 2-(4-(2-(aminoiminomethyl)hydrazinylidene)-2,5-cyclohexadien-1-ylidene)-

77. N''-{(1z,4z)-4-[(aminocarbonothioyl)hydrazono]cyclohexa-2,5-dien-1-ylidene}carbonohydrazonic Diamide

2.4 Create Date

2005-07-11

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₁N₇S
Molecular Weight	237.29 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	237.07966455 g/mol
Monoisotopic Mass	237.07966455 g/mol
Topological Polar Surface Area	159 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	289
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 Pharmacology and Biochemistry

4.1 ATC Code

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA01 - Ambazone

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