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Semicarbazide Hydrochloride

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Also known as: 563-41-7, Aminourea hydrochloride, Hydrazinecarboxamide hydrochloride, Semicarbazide hcl, Hydrazinecarboxamide, monohydrochloride, Semicarbazide chloride

Molecular Formula

CH₆ClN₃O

Molecular Weight

111.53 g/mol

InChI Key

XHQYBDSXTDXSHY-UHFFFAOYSA-N

FDA UNII

34854VG84B

1 2D Structure

Semicarbazide Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

aminourea;hydrochloride

2.1.2 InChI

InChI=1S/CH5N3O.ClH/c2-1(5)4-3;/h3H2,(H3,2,4,5);1H

2.1.3 InChI Key

XHQYBDSXTDXSHY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C(=O)(N)NN.Cl

2.2 Other Identifiers

2.2.1 UNII

34854VG84B

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 563-41-7

2. Aminourea Hydrochloride

3. Hydrazinecarboxamide Hydrochloride

4. Semicarbazide Hcl

5. Hydrazinecarboxamide, Monohydrochloride

6. Semicarbazide Chloride

7. Amidourea Hydrochloride

8. Carbamylhydrazine Hydrochloride

9. Hydrazinecarboxamide Monohydrochloride

10. Semicarbazide Monohydrochloride

11. Carbamyl Hydrazine.hcl

12. Hydrazinecarboxamide, Hydrochloride

13. Ek 226

14. Semicarbazide, Monohydrochloride

15. Aminourea;hydrochloride

16. Semicarbazide, Hydrochloride

17. Semicarbazide (hydrochloride)

18. Chebi:82532

19. Nsc-4732

20. 34854vg84b

21. Ccris 556

22. Hsdb 5197

23. Semicarbazide Hydrochloride (van)

24. Nsc 4732

25. Einecs 209-247-0

26. Semikarbazide Hydrochloride

27. Hydrazinecarboxamide, Hydrochloride (van)

28. Ai3-52680

29. Unii-34854vg84b

30. Hydrazine Carboxamide Hydrochloride

31. Mfcd00013009

32. Semicarbazide Hcl Salt

33. N-aminoureahydrochloride

34. Nh2nhconh2.hcl

35. Semicarbazide Hydrocloride

36. Dsstox_cid_244

37. Semicarbazide-hydrochloride

38. Semicarbazide.hydrochloride

39. Wln: Zvmz &gh

40. Semi-carbazide Hydrochloride

41. Schembl6932

42. Dsstox_rid_75458

43. Dsstox_gsid_20244

44. Mls002153236

45. Hydrochloric Acid Semicarbazide

46. Hydrazinecarboxamidehydrochloride

47. Sca-hcl-13c,15n2

48. Chembl1256355

49. Dtxsid4020244

50. Nsc4732

51. Hydrazinecarbox-amide Hydrochloride

52. Hy-y0470

53. Str00205

54. Semicarbazide Hydrochloride, >=99%

55. Tox21_200950

56. Tox21_501096

57. Akos015848282

58. Ccg-222400

59. Cs-w018530

60. Lp01096

61. Semicarbazide Hydrochloride [mi]

62. Ncgc00091589-01

63. Ncgc00094369-01

64. Ncgc00258503-01

65. Ncgc00261781-01

66. Cas-563-41-7

67. Semicarbazide Hydrochloride [hsdb]

68. Semicarbazide Hydrochloride [iarc]

69. Smr000326716

70. Hydrazinecarboxamide, Hydrochloride (1:1)

71. Semicarbazide Hydrochloride, P.a., 99.0%

72. Eu-0101096

73. Ft-0632395

74. Ft-0674553

75. C19521

76. D77852

77. S 2201

78. S-2460

79. Sr-01000075648

80. Sr-01000075648-2

81. Q27156046

82. F1908-0069

83. Semicarbazide Hydrochloride, Purum P.a., >=98.0% (at)

84. Semicarbazide Hydrochloride, Saj Special Grade, >=99.0%

85. Semicarbazide Hydrochloride, Vetranal(tm), Analytical Standard

86. 873205-62-0

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	CH₆ClN₃O
Molecular Weight	111.53 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	111.0199395 g/mol
Monoisotopic Mass	111.0199395 g/mol
Topological Polar Surface Area	81.1 Å²
Heavy Atom Count	6
Formal Charge	0
Complexity	42.2
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	2

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

... Binds to cytosine residues in RNA, to deoxycytosine residues in DNA in vitro and to cytosine and deoxycytosine nucleosides

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V12 212

4.2 Mechanism of Action

Semicarbazide, a hydrazine derivative, is carcinogenic to mice but shows no or little mutagenicity in the Salmonella-microsome test. To clarify whether or not the genotoxic mechanism contributes to the non-mutagenic carcinogenicity of semicarbazide, ...DNA damage induced by semicarbazide /was investigated/ using 32P-5'-end-labeled DNA fragments obtained from the c-Ha-ras-1 protooncogene and the p53 tumor suppressor gene. Semicarbazide caused DNA damage frequently at the thymine and cytosine residues in the presence of Cu(II). Catalase and bathocuproine partially inhibited DNA damage, suggesting that hydrogen peroxide plus Cu(I) participates in DNA damage. When a high concentration of semicarbazide was used in the presence of catalase, DNA damage was induced, especially at G in 5'-AG and slightly at 5'-G in GG and GGG sequences. An electron paramagnetic resonance (EPR) spectroscopic study has confirmed that the reaction of semicarbazide with Cu(II) produces carbamoyl radicals (.CONH2), possibly generated via the nitrogen-centered radicals of semicarbazide. Azodicarbonamide also produced carbamoyl radicals and induced DNA damage frequently at 5'-G in GG and GGG sequences, suggesting that carbamoyl radicals participate in this sequence-specific DNA damage by semicarbazide. On the basis of... previous reports, ...the sequence-specific DNA damage at G in 5'-AG in the present study is due to the nitrogen-centered radicals. This study has shown that semicarbazide induces DNA damage in the presence of Cu(II) through the formation of hydrogen peroxide and Cu(I). In addition, semicarbazide-derived free radicals participate in DNA damage. DNA damage induced by these reactive species may be relevant to the carcinogenicity of semicarbazide. /Semicarbazide/

Hirakawa K et al; Mut Res/Gen Toxicol and Environ Mutagen 536 (1-2): 91-101 (2003)

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