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39 FDA Orange Book
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3 South Africa
8 Listed Dossiers

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Chemistry

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Also known as: Kanamycin a sulfate, Kanamycin monosulfate, 25389-94-0, Kanamycin acid sulfate, Kanamycin a sulphate, Kanamycin (sulfate)

Molecular Formula

C₁₈H₃₈N₄O₁₅S

Molecular Weight

582.6 g/mol

InChI Key

OOYGSFOGFJDDHP-KMCOLRRFSA-N

FDA UNII

J80EX28SMQ

Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.

1 2D Structure

Kanamycin Sulfate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol;sulfuric acid

2.1.2 InChI

InChI=1S/C18H36N4O11.H2O4S/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17;1-5(2,3)4/h4-18,23-29H,1-3,19-22H2;(H2,1,2,3,4)/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-;/m1./s1

2.1.3 InChI Key

OOYGSFOGFJDDHP-KMCOLRRFSA-N

2.1.4 Canonical SMILES

C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)O)O)OC3C(C(C(C(O3)CO)O)N)O)N.OS(=O)(=O)O

2.1.5 Isomeric SMILES

C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N.OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

J80EX28SMQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Kanamycin

2. Kanamycin A

3. Kantrex

2.3.2 Depositor-Supplied Synonyms

1. Kanamycin A Sulfate

2. Kanamycin Monosulfate

3. 25389-94-0

4. Kanamycin Acid Sulfate

5. Kanamycin A Sulphate

6. Kanamycin (sulfate)

7. Ophtalmokalixan

8. 133-92-6

9. Kanamycin Monosulphate

10. 3847-27-6

11. J80ex28smq

12. Kanamycin Monosulfate [jan]

13. Kanamycin A Monosulfate

14. Chebi:6109

15. Nsc-757068

16. (2r,3s,4s,5r,6r)-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-diamino-3-[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol;sulfuric Acid

17. Dsstox_cid_27524

18. Dsstox_rid_82394

19. Dsstox_gsid_47524

20. Cristalomicina

21. Kanabristol

22. Kanamytrex

23. Otokalixin

24. Cantrex

25. Kanacedin

26. Kanaqua

27. Kanasig

28. Kanatrol

29. Kanescin

30. Kanicin

31. Kannasyn

32. Kantrim

33. Kano

34. (2r,3s,4s,5r,6r)-2-(aminomethyl)-6-(((1r,2r,3s,4r,6s)-4,6-diamino-3-(((2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)tetrahydro-2h-pyran-3,4,5-triol Sulfate

35. Kanamycin Sulfate [jan]

36. Unii-j80ex28smq

37. Kanamycin Sulfate [usp:jan]

38. Mfcd00070253

39. Kanamycin Sulfate From Streptomyces Kanamyceticus, Animal Component-free

40. Einecs 223-347-1

41. Einecs 246-933-9

42. Kantrex (tn)

43. Kanamycin, Sulfate (1:1) (salt)

44. Kanamycin Sulfate (tn)

45. Kanamycin Sulfate (usp)

46. Ncgc00016792-01

47. Kanamycin Sulfate Solution

48. Kanamycin Sulfate (jp17)

49. Kanamycin Sulphate (1:1)

50. Cas-25389-94-0

51. Chembl1446

52. Schembl65538

53. Kanamycin Mono Sulfate

54. Kanamycin Monosulfate (jp17)

55. Dtxsid1047524

56. Hms500b06

57. Kuc109575ac

58. Kanamycin A Sulfate [mi]

59. Kanamycin Sulfate [vandf]

60. Hms2096o09

61. Hms3713o09

62. Kanamycin Sulfate [usp-rs]

63. Kanamycin Sulfate [who-dd]

64. D-streptamine, O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-->6)-o-[6-amino-6-deoxy-alpha-d-glucopyranosyl-(1-->4)]-2-deoxy-, Sulfate (1:1)

65. Ksc-27-052c

66. Tox21_110612

67. Tox21_202817

68. Hy-16566a

69. S2315

70. C18h36n4o11 .h2o4s

71. Akos025310124

72. Kanamycin Sulfate [green Book]

73. Ccg-220394

74. Cs-1140

75. Kanamycin Sulfate [orange Book]

76. Nsc 757068

77. Kanamycin Sulfate [usp Monograph]

78. Ncgc00260363-01

79. Kanamycin Monosulfate, Cell Culture Grade

80. Kanamycin Sulfate 100 Microg/ml In Water

81. Kanamycin Monosulfate [ep Monograph]

82. K0047

83. C08046

84. D00866

85. D03262

86. 133k926

87. Q27107073

88. Kanamycin Sulfate Streptomyces Kanamyceticus, Powder, Gamma-irradiated

89. Kanamycin Sulfate From Streptomyces Kanamyceticus, Meets Usp Testing Specifications, Powder

90. Kanamycin Sulfate, Mixture Of Kanamycin A (main Component) And Kanamycin B And C

91. Kanamycin Sulfate, Pharmaceutical Secondary Standard; Certified Reference Material

92. (2r,3s,4s,5r,6r)-2-(aminomethyl)-6-((1r,2r,3s,4r,6s)-4,6-diamino-3-((2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-2-hydroxycyclohexyloxy)tetrahydro-2h-pyran-3,4,5-triol Sulfate

93. (2r,3s,4s,5r,6r)-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-bis(azanyl)-3-[(2s,3r,4s,5s,6r)-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-2-oxidanyl-cyclohexyl]oxy-oxane-3,4,5-triol Sulphate

94. .alpha.-d-glucopyranoside, (1s,2r,3r,4s,6r)-4,6-diamino-3-[(6-amino-6-deoxy-.alpha.-d-glucopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-, Sulfate (1:1) (salt)

95. D-streptamine, O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl(1->6)-o-(6-amino-6-deoxy-.alpha.-d-glucopyranosyl(1->4))-2-deoxy-, Sulfate (1:1) (salt)

96. D-streptamine, O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl(1->6)-o-(6-amino-6-deoxy-.alpha.-d-glucopyranosyl(1->4))-2-deoxy-, Sulphate (1:1) (salt)

97. D-streptamine, O-3-amino-3-deoxy-alpha-d-glucopyranosyl(1->6)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl(1->4))-2-deoxy-, Sulfate (1:1) (salt)

98. D-streptamine, O-3-amino-3-deoxy-alpha-d-glucopyranosyl(1-6)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl(1-4))-2-deoxy-, Sulfate (1:1) (salt)

99. Kanamycin Sulfate From Streptomyces Kanamyceticus, Powder, Bioreagent, Suitable For Cell Culture, Suitable For Plant Cell Culture

100. O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1->6)-o-[6-amino-6-deoxy-alpha-d-glucopyranosyl-(1->4)]-2-deoxy-d-streptamine Monosulfate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₈N₄O₁₅S
Molecular Weight	582.6 g/mol
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	6
Exact Mass	582.20543769 g/mol
Monoisotopic Mass	582.20543769 g/mol
Topological Polar Surface Area	366 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	720
Isotope Atom Count	0
Defined Atom Stereocenter Count	15
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Kanamycin sulfate
Active Ingredient	Kanamycin sulfate
Dosage Form	Injectable
Route	Injection
Strength	eq 1gm base/3ml; eq 500mg base/2ml
Market Status	Prescription
Company	Fresenius Kabi Usa

2 of 2
Drug Name	Kanamycin sulfate
Active Ingredient	Kanamycin sulfate
Dosage Form	Injectable
Route	Injection
Strength	eq 1gm base/3ml; eq 500mg base/2ml
Market Status	Prescription
Company	Fresenius Kabi Usa

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

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API Reference Price

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