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    Chemistry

    Click the arrow to open the dropdown
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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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    28-Jan-2021
    03-Aug-2024
    KGS
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    DOSAGE - INJECTABLE;INJECTION - 1GM/VIAL

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