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Amikacin Sulfate

Synopsis, Chemistry

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Also known as: Amikacin disulfate, 39831-55-5, Pierami, Amikin, Amikacin bis(sulphate), Kaminax

Molecular Formula

C₂₂H₄₇N₅O₂₁S₂

Molecular Weight

781.8 g/mol

InChI Key

FXKSEJFHKVNEFI-GCZBSULCSA-N

FDA UNII

N6M33094FD

A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.

1 2D Structure

Amikacin Sulfate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C22H43N5O13.2H2O4S/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21;2*1-5(2,3)4/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);2*(H2,1,2,3,4)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;;/m0../s1

2.1.3 InChI Key

FXKSEJFHKVNEFI-GCZBSULCSA-N

2.1.4 Canonical SMILES

C1C(C(C(C(C1NC(=O)C(CCN)O)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)O)N.OS(=O)(=O)O.OS(=O)(=O)O

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

N6M33094FD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. A.m.k

2. Amikacin

3. Amikacina Medical

4. Amikacina Normon

5. Amikafur

6. Amikalem

7. Amikason's

8. Amikayect

9. Amikin

10. Amiklin

11. Amukin

12. Bb K 8

13. Bb K8

14. Bb-k 8

15. Bb-k8

16. Bbk 8

17. Bbk8

18. Biclin

19. Biklin

20. Gamikal

21. Kanbine

22. Medical, Amikacina

23. Normon, Amikacina

24. Oprad

25. Sulfate, Amikacin

26. Yectamid

2.3.2 Depositor-Supplied Synonyms

1. Amikacin Disulfate

2. 39831-55-5

3. Pierami

4. Amikin

5. Amikacin Bis(sulphate)

6. Kaminax

7. Bb-k8

8. Arikayce

9. Amikacin Sulphate

10. Amikacin Disulphate

11. Amikacin (disulfate)

12. Amikacin (as Sulfate)

13. Amikacin Sulfate Salt

14. Amikacin Disulfate Salt

15. N6m33094fd

16. Nsc-755846

17. Amikafur

18. Amitrex

19. Biodacyn

20. Chemacin

21. Fabianol

22. Likacin

23. Biklin

24. Kancin-gap

25. Antibiotic Bb-k8 Sulfate

26. (2s)-4-amino-n-[(1r,2s,3s,4r,5s)-5-amino-2-(3-amino-3-deoxy-alpha-d-glucopyranosyloxy)-4-(6-amino-6-deoxy-alpha-d-glucopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide Disulfate

27. Amikacin (sulfate)

28. O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1->4)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl-(1->6))-n(3)-(4-amino-l-2-hydroxybutyryl)-2-deoxy-l-streptamine Sulfate (1:2)

29. Nn-k 8

30. Einecs 254-648-6

31. Amikan

32. Unii-n6m33094fd

33. Amikacini Sulfas

34. Amikacin Sulfate [usan:usp:jan]

35. Amikin (tn)

36. Amikin In Sodium Chloride 0.9% In Plastic Container

37. (2s)-4-amino-n-[(1r,2s,3s,4r,5s)-5-amino-2-[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2r,3r,4s,5s,6r)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]

38. Amikacin Sulfate In Sodium Chloride 0.9% In Plastic Container

39. Bay-416651 Sulfate

40. Amikacin Sulfate [mi]

41. Amikacin Sulfate [jan]

42. Amikacin Sulfate (jp17/usp)

43. Chebi:2638

44. Schembl1649432

45. Amikacin Sulfate [usan]

46. Amikacin Sulfate [vandf]

47. Chembl4208954

48. Hy-b0509b

49. Amikacin Sulfate [mart.]

50. Amikacin Sulfate [usp-rs]

51. Amikacin Sulfate [who-dd]

52. Amikacini Sulfas [who-ip]

53. Dtxsid601045247

54. Mfcd00167475

55. S3065

56. Amikacin Sulfate [green Book]

57. Akos025310105

58. Amikacin Sulfate [ep Impurity]

59. Amikacin Sulfate [orange Book]

60. Amikacin Sulfate [ep Monograph]

61. Ccg-270466

62. Cs-3493

63. Nsc 755846

64. Amikacin Sulfate [usp Monograph]

65. As-13777

66. D-streptamine, O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-6)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl-(1-4))-n(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (s)-, Sulfate (1:2)(salt)

67. O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl-(1-6))-n(sup 3)-(4-amino-l-2-hydroxybutyryl)-2-deoxy-l-streptamine Sulfate (1:2)

68. D00865

69. 831a555

70. Q27105754

71. Amikacin Sulfate, European Pharmacopoeia (ep) Reference Standard

72. Amikacin Disulfate Salt, Potency: 674-786 Mug Per Mg (as Amikacin Base)

73. Amikacin Sulfate, United States Pharmacopeia (usp) Reference Standard

74. Amikacin For System Suitability, European Pharmacopoeia (ep) Reference Standard

75. Amikacin Sulfate, Pharmaceutical Secondary Standard; Certified Reference Material

76. (2s)-4-amino-n-{(1r,2s,3s,4r,5s)-5-amino-2-[(3-amino-3-deoxy-alpha-d-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-alpha-d-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide Sulfate (1:2)

77. (s)-4-amino-n-((1r,2s,3s,4r,5s)-5-amino-2-(((2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-4-(((2r,3r,4s,5s,6r)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2h-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide Bis(sulfate)

78. D-streptamine, O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl-(1->6)-o-(6-amino-6-deoxy-.alpha.-d-glucopyranosyl-(1->4))-n(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (s)-, Sulfate (1:2) (salt)

79. D-streptamine, O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl-(1->6)-o-(6-amino-6-deoxy-.alpha.-d-glucopyranosyl-(1->4))-n(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (s)-, Sulphate (1:2) (salt)

80. D-streptamine, O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1.fwdarw.6)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl-(1.fwdarw.4))-n1-((2s)-4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, Sulfate (1:2) (salt)

81. O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl-(1->4)-o-(6-amino-6-deoxy-.alpha.-d-glucopyranosyl-(1->6))-n(sup 3)-(4-amino-l-2-hydroxybutyryl)-2-deoxy-l-streptamine Sulfate (1:2)

82. O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl-(1->4)-o-(6-amino-6-deoxy-.alpha.-d-glucopyranosyl-(1->6))-n(sup 3)-(4-amino-l-2-hydroxybutyryl)-2-deoxy-l-streptamine Sulphate (1:2)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₄₇N₅O₂₁S₂
Molecular Weight	781.8 g/mol
Hydrogen Bond Donor Count	17
Hydrogen Bond Acceptor Count	25
Rotatable Bond Count	10
Exact Mass	781.22049587 g/mol
Monoisotopic Mass	781.22049587 g/mol
Topological Polar Surface Area	498 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	900
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Amikacin sulfate
Drug Label	Amikacin Sulfate Injection USP is a semi-synthetic aminoglycoside antibiotic derived from kanamycin. D-Streptamine,O-3-amino-3-deoxy--D-glucopyranosyl-(16)-O-[6-amino-6-deoxy--D-glucopyranosyl-(14)]-N1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy...
Active Ingredient	Amikacin sulfate
Dosage Form	Injectable
Route	Injection
Strength	eq 50mg base/ml; eq 250mg base/ml
Market Status	Prescription
Company	Emcure Pharms; Teva Pharms Usa; Eurohlth Intl

2 of 2
Drug Name	Amikacin sulfate
Drug Label	Amikacin Sulfate Injection USP is a semi-synthetic aminoglycoside antibiotic derived from kanamycin. D-Streptamine,O-3-amino-3-deoxy--D-glucopyranosyl-(16)-O-[6-amino-6-deoxy--D-glucopyranosyl-(14)]-N1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy...
Active Ingredient	Amikacin sulfate
Dosage Form	Injectable
Route	Injection
Strength	eq 50mg base/ml; eq 250mg base/ml
Market Status	Prescription
Company	Emcure Pharms; Teva Pharms Usa; Eurohlth Intl

4.2 Drug Indication

Treatment of nontuberculous mycobacterial lung infection, Treatment of Pseudomonas aeruginosa pulmonary infection / colonisation in patients with cystic fibrosis

Arikayce liposomal is indicated for the treatment of non-tuberculous mycobacterial (NTM) lung infections caused by Mycobacterium avium Complex (MAC) in adults with limited treatment options who do not have cystic fibrosis.

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Aminoglycosides [CS]; Aminoglycoside Antibacterial [EPC]

5.3 ATC Code

J01GB06