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Chemistry

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Also known as: Azactam, 78110-38-0, Primbactam, Azthreonam, Nebactam, Azonam
Molecular Formula
C13H17N5O8S2
Molecular Weight
435.4  g/mol
InChI Key
WZPBZJONDBGPKJ-VEHQQRBSSA-N
FDA UNII
G2B4VE5GH8

Aztreonam
A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms.
Aztreonam is a Monobactam Antibacterial.
1 2D Structure

Aztreonam

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid
2.1.2 InChI
InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1
2.1.3 InChI Key
WZPBZJONDBGPKJ-VEHQQRBSSA-N
2.1.4 Canonical SMILES
CC1C(C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)C2=CSC(=N2)N
2.1.5 Isomeric SMILES
C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)NC(=O)/C(=N\OC(C)(C)C(=O)O)/C2=CSC(=N2)N
2.2 Other Identifiers
2.2.1 UNII
G2B4VE5GH8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Az Threonam

2. Az-threonam

3. Azactam

4. Azthreonam

5. Sq 26,776

6. Sq-26,776

7. Sq26,776

8. Urobactam

2.3.2 Depositor-Supplied Synonyms

1. Azactam

2. 78110-38-0

3. Primbactam

4. Azthreonam

5. Nebactam

6. Azonam

7. Aztreon

8. Rel-aztreonam

9. Sq 26776

10. Sq-26776

11. Nsc646279

12. Chembl158

13. Nsc-646279

14. 149496-40-2

15. Aztreonam E-isomer

16. Nsc-758913

17. 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2s,3s)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic Acid

18. Mfcd00072145

19. G2b4ve5gh8

20. Chebi:161680

21. Squibb 26776

22. Sr-01000841814

23. 2-[[(z)-[1-(2-amino-4-thiazolyl)-2-[[(2s,3s)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropionic Acid

24. (z)-2-((((2-amino-4-thiazolyl)(((2s,3s)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic Acid

25. Aztreonam (azactam, Cayston)

26. Azetreonam

27. E-aztreonam

28. Prestwick_914

29. Aztreonam [inn]

30. Aztreonam [jan]

31. Aztreonam [mi]

32. Aztreonam [usan]

33. Prestwick2_000185

34. Prestwick3_000185

35. Aztreonam [vandf]

36. Aztreonam [mart.]

37. Aztreonam [usp-rs]

38. Aztreonam [who-dd]

39. Bspbio_000109

40. [2s-[2alpha,3beta(z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic Acid

41. Mls003915628

42. Mls006011974

43. Aztreonam, Analytical Standard

44. Bidd:gt0765

45. Bpbio1_000121

46. Aztreonam [orange Book]

47. Dtxsid0022640

48. Aztreonam [usp Monograph]

49. Bcpp000356

50. Hms1568f11

51. Hms2090k09

52. Hms2095f11

53. Hms3712f11

54. Hy-b0129

55. Bdbm50240480

56. Zinc12503091

57. Akos015840157

58. Akos015961777

59. Ac-4330

60. Bcp9000372

61. Ccg-220185

62. Cs-1902

63. Ncgc00179656-01

64. 2-({[(1z)-1-(2-amino-1,3-thiazol-4-yl)-2-{[(2s,3s)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino}-2-oxoethylidene]amino}oxy)-2-methylpropanoic Acid

65. 2-[(z)-[1-(2-aminothiazol-4-yl)-2-[[(2s,3s)-2-methyl-4-oxo-1-sulfo-azetidin-3-yl]amino]-2-oxo-ethylidene]amino]oxy-2-methyl-propanoic Acid

66. As-13760

67. Smr002204030

68. Smr004703537

69. So 26776

70. S1505

71. 110a380

72. Sr-01000841814-2

73. Sr-01000841814-3

74. Brd-k62607865-001-03-0

75. Q27262730

76. Aztreonam, United States Pharmacopeia (usp) Reference Standard

77. Aztreonam, Pharmaceutical Secondary Standard; Certified Reference Material

78. (2s,3s)-3-({(2z)-2-(2-ammonio-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]ethanoyl}amino)-2-methyl-4-oxoazetidine-1-sulfonate

79. (2s,3s)-3-({(2z)-2-(2-ammonio-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]ethanoyl}amino)-2-methyl-4-oxoazetidine-1-sulfonate(aztreonam)

80. 2-((((e)-1-(2-aminothiazol-4-yl)-2-(((2s,3s)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic Acid

81. 2-((((z)-1-(2-aminothiazol-4-yl)-2-(((2s,3s)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic Acid

82. 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2s)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic Acid

83. 2-[1-(2-amino-thiazol-4-yl)-1-((2s,3s)-2-methyl-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(z)-ylideneaminooxy]-2-methyl-propionic Acid

84. 2-aminothiazol-4-yl)-2-((2s,3s)-2-methyl-4-oxo-1-sulfoazetidin-3-ylamino)-2-oxoethylideneaminooxy)-2-methylpropanoic Acid

85. 80951-91-3

86. Propanoic Acid, 2-(((1-(2-amino-4-thiazolyl)-2-((2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino)-2-oxoethylidene)amino)oxy)-2-methyl-, (2s-(2.alpha.,3.beta.(z)))-

87. Propanoic Acid, 2-[[(z)-[1-(2-amino-4-thiazolyl)-2-[[(2s,3s)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methyl-

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 435.4 g/mol
Molecular Formula C13H17N5O8S2
XLogP30.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass435.05185486 g/mol
Monoisotopic Mass435.05185486 g/mol
Topological Polar Surface Area238 Ų
Heavy Atom Count28
Formal Charge0
Complexity808
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAzactam
PubMed HealthAztreonam (Injection)
Drug ClassesAntibiotic
Drug LabelAZACTAM (aztreonam injection) contains the active ingredient aztreonam, a monobactam. It was originally isolated from Chromobacterium violaceum. It is a synthetic bactericidal antibiotic.The monobactams, having a unique monocyclic beta-lactam nucle...
Active IngredientAztreonam
Dosage FormInjectable
RouteInjection
Strength2gm/vial; 1gm/vial
Market StatusPrescription
CompanyBristol Myers Squibb

2 of 6  
Drug NameAztreonam
PubMed HealthAztreonam
Drug ClassesAntibiotic
Drug LabelAZACTAM (aztreonam injection) contains the active ingredient aztreonam, a monobactam. It was originally isolated from Chromobacterium violaceum. It is a synthetic bactericidal antibiotic.The monobactams, having a unique monocyclic beta-lactam nucle...
Active IngredientAztreonam
Dosage FormInjectable
RouteInjection
Strength500mg/vial; 2gm/vial; 1gm/vial
Market StatusPrescription
CompanyFresenius Kabi Usa; Eurohlth Intl

3 of 6  
Drug NameCayston
PubMed HealthAztreonam
Drug ClassesAntibiotic
Active IngredientAztreonam
Dosage FormFor solution
RouteInhalation
Strength75mg/vial
Market StatusPrescription
CompanyGilead

4 of 6  
Drug NameAzactam
PubMed HealthAztreonam (Injection)
Drug ClassesAntibiotic
Drug LabelAZACTAM (aztreonam injection) contains the active ingredient aztreonam, a monobactam. It was originally isolated from Chromobacterium violaceum. It is a synthetic bactericidal antibiotic.The monobactams, having a unique monocyclic beta-lactam nucle...
Active IngredientAztreonam
Dosage FormInjectable
RouteInjection
Strength2gm/vial; 1gm/vial
Market StatusPrescription
CompanyBristol Myers Squibb

5 of 6  
Drug NameAztreonam
PubMed HealthAztreonam
Drug ClassesAntibiotic
Drug LabelAZACTAM (aztreonam injection) contains the active ingredient aztreonam, a monobactam. It was originally isolated from Chromobacterium violaceum. It is a synthetic bactericidal antibiotic.The monobactams, having a unique monocyclic beta-lactam nucle...
Active IngredientAztreonam
Dosage FormInjectable
RouteInjection
Strength500mg/vial; 2gm/vial; 1gm/vial
Market StatusPrescription
CompanyFresenius Kabi Usa; Eurohlth Intl

6 of 6  
Drug NameCayston
PubMed HealthAztreonam
Drug ClassesAntibiotic
Active IngredientAztreonam
Dosage FormFor solution
RouteInhalation
Strength75mg/vial
Market StatusPrescription
CompanyGilead

4.2 Drug Indication

Cayston is indicated for the suppressive therapy of chronic pulmonary infections due to Pseudomonas aeruginosa in patients with cystic fibrosis (CF) aged 6 years and older.

Consideration should be given to official guidance on the appropriate use of antibacterial agents.


Treatment of Gram-negative endobronchial infection in bronchiectasis patients


Treatment of Pseudomonas aeruginosa pulmonary infection / colonisation in patients with 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 Active Moiety
AZTREONAM
5.2.2 FDA UNII
G2B4VE5GH8
5.2.3 Pharmacological Classes
Monobactams [CS]; Monobactam Antibacterial [EPC]
5.3 ATC Code

J01DF01


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DF - Monobactams

J01DF01 - Aztreonam


API Reference Price

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06-Feb-2021
29-Aug-2024
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - INJECTABLE;INJECTION - 1GM/VIAL

USFDA APPLICATION NUMBER - 50580

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DOSAGE - INJECTABLE;INJECTION - 2GM/VIAL

USFDA APPLICATION NUMBER - 50580

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DOSAGE - INJECTABLE;INJECTION - 20MG/ML

USFDA APPLICATION NUMBER - 50632

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DOSAGE - INJECTABLE;INJECTION - 40MG/ML

USFDA APPLICATION NUMBER - 50632

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