Aztreonam

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

INJECTABLE;INJECTION - 1GM/VIAL, INJECTABLE;INJECTION - 2GM/VIAL, INJECTABLE;INJECTION - 20MG/ML, INJECTABLE;INJECTION - 40MG/ML

INJECTABLE;INJECTION - 1GM/VIAL
INJECTABLE;INJECTION - 2GM/VIAL
INJECTABLE;INJECTION - 20MG/ML
INJECTABLE;INJECTION - 40MG/ML

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Suppliers, 4 Roquette, 1 Pfanstiehl, 1 DKSH

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2 Parenteral, 2 Fillers, Diluents & Binders, 1 Thickeners and Stabilizers, 1 Topical

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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

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 Formula	C₁₃H₁₇N₅O₈S₂
Molecular Weight	435.4 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	7
Exact Mass	435.05185486 g/mol
Monoisotopic Mass	435.05185486 g/mol
Topological Polar Surface Area	238 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	808
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Azactam
PubMed Health	Aztreonam (Injection)
Drug Classes	Antibiotic
Drug Label	AZACTAM (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 Ingredient	Aztreonam
Dosage Form	Injectable
Route	Injection
Strength	2gm/vial; 1gm/vial
Market Status	Prescription
Company	Bristol Myers Squibb

2 of 6
Drug Name	Aztreonam
PubMed Health	Aztreonam
Drug Classes	Antibiotic
Drug Label	AZACTAM (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 Ingredient	Aztreonam
Dosage Form	Injectable
Route	Injection
Strength	500mg/vial; 2gm/vial; 1gm/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; Eurohlth Intl

3 of 6
Drug Name	Cayston
PubMed Health	Aztreonam
Drug Classes	Antibiotic
Active Ingredient	Aztreonam
Dosage Form	For solution
Route	Inhalation
Strength	75mg/vial
Market Status	Prescription
Company	Gilead

4 of 6
Drug Name	Azactam
PubMed Health	Aztreonam (Injection)
Drug Classes	Antibiotic
Drug Label	AZACTAM (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 Ingredient	Aztreonam
Dosage Form	Injectable
Route	Injection
Strength	2gm/vial; 1gm/vial
Market Status	Prescription
Company	Bristol Myers Squibb

5 of 6
Drug Name	Aztreonam
PubMed Health	Aztreonam
Drug Classes	Antibiotic
Drug Label	AZACTAM (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 Ingredient	Aztreonam
Dosage Form	Injectable
Route	Injection
Strength	500mg/vial; 2gm/vial; 1gm/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; Eurohlth Intl

6 of 6
Drug Name	Cayston
PubMed Health	Aztreonam
Drug Classes	Antibiotic
Active Ingredient	Aztreonam
Dosage Form	For solution
Route	Inhalation
Strength	75mg/vial
Market Status	Prescription
Company	Gilead

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

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Aztreonam

Aztreonam

Synopsis

Chemistry

APIs // Active Pharmaceutical Ingredients

20 API Suppliers

11 USDMF

1 JDMF

9 NDC API

10 Listed Suppliers

DEVELOPMENTS

2 Drug(s) in Development

PRICE INFORMATION

API Reference Price

API Exports

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INTERMEDIATES

5 Suppliers

DOSSIERs // Finished Dosage Formulations

40 Dossiers

14 FDA Orange Book

8 Europe

1 Canada

1 South Africa

16 Listed Dossiers

DRUG PRODUCT COMPOSITION

INJECTABLE;INJECTION - 1GM/VIAL

INJECTABLE;INJECTION - 2GM/VIAL

INJECTABLE;INJECTION - 20MG/ML

INJECTABLE;INJECTION - 40MG/ML

RELATED EXCIPIENT COMPANIES

Suppliers

4 Roquette

1 Pfanstiehl

1 DKSH

EXCIPIENTS BY APPLICATIONS

2 Parenteral

2 Fillers, Diluents & Binders

1 Thickeners and Stabilizers

1 Topical

GLOBAL SALES INFORMATION

24 US Medicaid Prescriptions

5 Finished Drug Prices

MARKET PLACE

9 APIs

4 DOSSIERS // FDF

PATENTS

14 Health Canada Patents

ANALYTICAL SOLUTION(s)

3 USP Standards

2 Other Ref. Standards

DIGITAL CONTENT

12 News

API SUPPLIERS

API REF. PRICE (USD / KG)

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