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    Sulbactam

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

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    2D Structure
    Also known as: 68373-14-8, Sulbactam acid, Betamaze, Penicillanic acid sulfone, (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide, Sulbactamum
    Molecular Formula
    C8H11NO5S
    Molecular Weight
    233.24  g/mol
    InChI Key
    FKENQMMABCRJMK-RITPCOANSA-N
    FDA UNII
    S4TF6I2330
    A beta-lactamase inhibitor with very weak antibacterial action. The compound prevents antibiotic destruction of beta-lactam antibiotics by inhibiting beta-lactamases, thus extending their spectrum activity. Combinations of sulbactam with beta-lactam antibiotics have been used successfully for the therapy of infections caused by organisms resistant to the antibiotic alone.
    Sulbactam is a beta Lactamase Inhibitor. The mechanism of action of sulbactam is as a beta Lactamase Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,5R)-3,3-dimethyl-4,4,7-trioxo-46-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
    2.1.3 InChI Key
    FKENQMMABCRJMK-RITPCOANSA-N
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)C
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    S4TF6I2330
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Btamaze

    2. Combactam

    3. Cp 45899

    4. Cp-45899

    5. Cp45899

    6. Penicillanic Acid Sulfone

    7. Sodium, Sulbactam

    8. Sulbactam Sodium

    9. Sulfone, Penicillanic Acid

    2.3.2 Depositor-Supplied Synonyms

    1. 68373-14-8

    2. Sulbactam Acid

    3. Betamaze

    4. Penicillanic Acid Sulfone

    5. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4,4-dioxide

    6. Sulbactamum

    7. Penicillanic Acid 1,1-dioxide

    8. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid 4,4-dioxide

    9. Chembl403

    10. Cp-45899

    11. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    12. Cp-45,899

    13. Chebi:9321

    14. S4tf6i2330

    15. Sulbactam (inn)

    16. 68373-14-8 (free Acid)

    17. Nsc-759886

    18. Sulbactam 100 Microg/ml In Acetonitrile

    19. Sulbactam [inn]

    20. Dsstox_cid_3605

    21. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    22. Dsstox_rid_77104

    23. Dsstox_gsid_23605

    24. 2,2-dimethyl-1,1-dioxidopenam-3alpha-carboxylic Acid

    25. Cp-458992

    26. Smr000387064

    27. Cas-68373-14-8

    28. Cp 45899

    29. Sulbactam [inn:ban]

    30. Sr-01000760610

    31. Sulbactamum [inn-latin]

    32. Mfcd00867005

    33. Unii-s4tf6i2330

    34. Sulbactam,(s)

    35. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4?^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    36. 0rn

    37. Einecs 269-878-2

    38. Sulbactam [mi]

    39. Sulbactam [vandf]

    40. Ncgc00159487-06

    41. Sulbactam; Sulbactam Acid

    42. Sulbactam [mart.]

    43. Sulbactam [usp-rs]

    44. Sulbactam [who-dd]

    45. Schembl47781

    46. Mls001048859

    47. Mls001304017

    48. Sodium 1,1-dioxypenicillanate

    49. Dtxsid1023605

    50. Gtpl10769

    51. Hms2090e07

    52. Hms2269a12

    53. Hms3651c06

    54. Hms3715b09

    55. Zinc897244

    56. Bcp13271

    57. Ex-a2000

    58. Hy-b0334

    59. Tox21_113642

    60. Bbl033518

    61. Bdbm50021954

    62. S1958

    63. Stk801889

    64. Akos004119988

    65. Tox21_113642_1

    66. Ccg-221124

    67. Db09324

    68. Ks-5198

    69. Nsc 759886

    70. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure 4,4-dioxid

    71. Sulbactam, Analytical Reference Material

    72. Ncgc00159336-02

    73. Ncgc00159336-03

    74. Ncgc00159336-05

    75. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2s-cis)-

    76. Ac-18973

    77. Bs167314

    78. S0868

    79. Sultamicillin Impurity A [ep Impurity]

    80. C07770

    81. D08533

    82. Ab00698109-06

    83. Ab00698109-08

    84. Ab00698109_09

    85. 373s148

    86. A836122

    87. Q423393

    88. Sr-01000760610-2

    89. Sr-01000760610-3

    90. Brd-k44133266-001-10-0

    91. Z1563146038

    92. Sulbactam, European Pharmacopoeia (ep) Reference Standard

    93. Sulbactam, United States Pharmacopeia (usp) Reference Standard

    94. (2s,5r)-2-carboxylato-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4,4-dioxide

    95. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    96. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid4,4-dioxide

    97. 3,3-dimethyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid

    98. Sulbactam For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    99. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid

    100. (2s,5r)-3,3-dimethyl-4,4,7-tris(oxidanylidene)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    101. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylic Acid 4,4-dioxide

    102. (2s,5r)?-?3,3-?dimethyl-?7-?oxo-?4-?thia-?1-?azabicyclo[3.2.0]?heptane-?2-?carboxylic Acid 4,4-dioxide

    103. (s)-3,3-dimethyl-7-(r)-oxo-4,4-dioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid

    104. 3,3-dimethyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid (sulbactam)

    105. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-,4,4-dioxide, (2s, Cis)

    106. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,3,3-dimethyl-7-oxo-, 4,4-dioxide, (2s,5r)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 233.24 g/mol
    Molecular Formula C8H11NO5S
    XLogP3-1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count1
    Exact Mass233.03579362 g/mol
    Monoisotopic Mass233.03579362 g/mol
    Topological Polar Surface Area100 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity446
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Sulbactam is currently available in combination products with ampicillin. Within this formulation it is indicated for the treatment of infections due to susceptible strains of the designated microorganisms in the conditions listed below. Skin and Skin Structure Infections caused by beta-lactamase producing strains of Staphylococcus aureus, Escherichia coli, Klebsiella spp. (including K. pneumoniae), Proteus mirabilis, Bacteroides fragilis, Enterobacter spp., and Acinetobacter calcoaceticus. Intra-Abdominal Infections caused by beta-lactamase producing strains of Escherichia coli, Klebsiella spp. (including K. pneumoniae), Bacteroides spp. (including B. fragilis), and Enterobacter spp. Gynecological Infections caused by beta-lactamase producing strains of Escherichia coli, and Bacteroides spp. (including B. fragilis).

    FDA Label

    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.)

    beta-Lactamase Inhibitors

    Endogenous substances and drugs that inhibit or block the activity of BETA-LACTAMASES. (See all compounds classified as beta-Lactamase Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    SULBACTAM
    5.2.2 FDA UNII
    S4TF6I2330
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - beta Lactamase Inhibitors
    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CG - Beta-lactamase inhibitors

    J01CG01 - Sulbactam

    5.4 Absorption, Distribution and Excretion

    Absorption

    Peak serum concentrations are reached almost immediately following a 15-minute intravenous infusion of sulbactam + ampicillin. Mean peak serum levels for sulbactam range from 48 to 88 mcg/mL following intravenous administration of 2000 mg of ampicillin plus 1000 mg sulbactam. After an intramuscular injection of 1000 mg ampicillin plus 500 mg sulbactam, peak sulbactam serum levels ranging from 6 to 24 mcg/mL are attained.

    Route of Elimination

    Approximately 75 to 85% of both ampicillin and sulbactam are excreted unchanged in the urine during the first 8 hours after administration.

    Volume of Distribution

    Penetration of both ampicillin and sulbactam into cerebrospinal fluid in the presence of inflamed meninges has been demonstrated after IV administration.

    5.5 Biological Half-Life

    ~1 hr

    5.6 Mechanism of Action

    Sulbactam is an irreversible inhibitor of -lactamase; by binding and inhibiting -lactamase produced by bacterial cells, sulbactam is thereby able to prevent it from reducing antibiotic activity. Although sulbactam alone possesses little useful antibacterial activity, except against the Neisseriaceae, whole organism studies have shown that sulbactam restores ampicillin activity against beta-lactamase producing strains. In particular, sulbactam has good inhibitory activity against the clinically important plasmid mediated beta-lactamases most frequently responsible for transferred drug resistance. The presence of sulbactam in formulations with ampicillin effectively extends the antibacterial spectrum of ampicillin to include many bacteria normally resistant to it and to other beta-lactam antibacterials. Thus, products with ampicillin + sulbactam possess the properties of a broad-spectrum antibacterial and a beta-lactamase inhibitor.