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    Cefotaxime
    Also known as: 64485-93-4, Cefotaxime sodium salt, Sodium cefotaxime, Hr 756, Cefotaxime, Ru 24756
    Molecular Formula
    C16H16N5NaO7S2
    Molecular Weight
    477.5  g/mol
    InChI Key
    AZZMGZXNTDTSME-JUZDKLSSSA-M
    FDA UNII
    258J72S7TZ
    Semisynthetic broad-spectrum cephalosporin.
    1 2D Structure

    Cefotaxime

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    sodium;(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C16H17N5O7S2.Na/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8;/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26);/q;+1/p-1/b20-9-;/t10-,14-;/m1./s1
    2.1.3 InChI Key
    AZZMGZXNTDTSME-JUZDKLSSSA-M
    2.1.4 Canonical SMILES
    CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)[O-].[Na+]
    2.1.5 Isomeric SMILES
    CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)[O-].[Na+]
    2.2 Other Identifiers
    2.2.1 UNII
    258J72S7TZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Benaxima

    2. Biosint

    3. Cefotaxim

    4. Cefotaxime

    5. Cefradil

    6. Cephotaxim

    7. Claforan

    8. Fotexina

    9. Hr 756

    10. Hr-756

    11. Hr756

    12. Kendrick

    13. Klaforan

    14. Primafen

    15. Ru 24756

    16. Ru-24756

    17. Ru24756

    18. Sodium, Cefotaxime

    19. Taporin

    2.3.2 Depositor-Supplied Synonyms

    1. 64485-93-4

    2. Cefotaxime Sodium Salt

    3. Sodium Cefotaxime

    4. Hr 756

    5. Cefotaxime

    6. Ru 24756

    7. (+)-cefotaxime Sodium Salt

    8. Hr-756

    9. Cefotaxime (sodium)

    10. Ru-24756

    11. Mls000028559

    12. Chebi:3498

    13. 258j72s7tz

    14. Sodium 7-(2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)cephalosporanate

    15. Cefotax

    16. Nsc-756666

    17. Sodium;(6r,7r)-3-(acetyloxymethyl)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    18. Smr000058812

    19. Tolycar

    20. Pretor

    21. Sodium (6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 7(sup 2)-(z)-(o-methyloxime), Acetate (ester)

    22. Sodium;(6r,7r)-3-(acetyloxymethyl)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    23. Cefotaxime (sodium Salt)

    24. Ralopar

    25. Tolycor

    26. Zariviz

    27. Claforan Sodium

    28. Mls002222330

    29. Cefotaxime Na-salt

    30. Cefotaxime Sodium Salt (syn-isomer)

    31. Smr001307269

    32. Mfcd00079073

    33. Unii-258j72s7tz

    34. Cefotaxim Sodium

    35. Claforan (tn)

    36. Prestwick_823

    37. Cefotaxime Sodium [usan:usp:jan]

    38. Einecs 264-915-9

    39. Cefotaxime, Sodium Salt

    40. Opera_id_1945

    41. Chembl1010

    42. Schembl41092

    43. Cefotaxime And Dextrose 2.4% In Plastic Container

    44. Cefotaxime And Dextrose 3.9% In Plastic Container

    45. Mls001077352

    46. Mls001333684

    47. Sym-methoxyimino Cephalosporin

    48. Claforan In Dextrose 5% In Plastic Container

    49. Cefotaxime Sodium [jan]

    50. Cefotaxime Sodium (jp17/usp)

    51. Cefotaxime Sodium [usan]

    52. Dtxsid4046991

    53. Cefotaxime Sodium [vandf]

    54. Cefotaxime Sodium [mart.]

    55. Claforan In Sodium Chloride 0.9% In Plastic Container

    56. Hms1568k20

    57. Hms2095k20

    58. Hms2233j21

    59. Hms3260h18

    60. Hms3712k20

    61. Cefotaxime Sodium [usp-rs]

    62. Cefotaxime Sodium [who-dd]

    63. Amy40166

    64. Cefotaxime Sodium Salt [mi]

    65. Hy-a0088

    66. Tox21_500278

    67. S4517

    68. Akos015951272

    69. Ccg-220139

    70. Ccg-221582

    71. Cefotaxime Sodium [ep Impurity]

    72. Cefotaxime Sodium [orange Book]

    73. Cs-4297

    74. Ks-1416

    75. Nsc 756666

    76. Cefotaxime Sodium [usp Impurity]

    77. Cefotaxime Sodium [usp Monograph]

    78. Ncgc00093734-01

    79. Ncgc00093734-02

    80. Ncgc00260963-01

    81. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-((acetyloxy)methyl)-7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, Monosodium Salt, (6r-(6alpha,7beta(z)))-

    82. Smr000653480

    83. Eu-0100278

    84. A16005

    85. C 7912

    86. C08113

    87. D00919

    88. Cefadroxil, Antibiotic For Culture Media Use Only

    89. Q-200807

    90. Cefotaxime Sodium Salt, Potency: 916-964 Mug Per Mg

    91. Cefotaxime Sodium, European Pharmacopoeia (ep) Reference Standard

    92. Cefotaxime Sodium Salt, Plant Cell Culture Tested, Bioreagent, Powder

    93. Cefotaxime Sodium, United States Pharmacopeia (usp) Reference Standard

    94. Cefotaxime For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    95. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-((acetyloxy)methyl)-7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, Monosodium Salt, (6r-(6.alpha.,7.beta.(z)))-

    96. Sodium (6r,7r)-3-(acetoxymethyl)-7-((e)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    97. Sodium (6r,7r)-3-(acetoxymethyl)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    98. Sodium (6r-(6alpha,7beta(z)))-3-(acetoxymethyl)-7-((2-aminothiazol-4-yl)(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

    99. Sodium 3-(acetoxymethyl)-7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3,4-didehydrocepham-4-carboxylate

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 477.5 g/mol
    Molecular Formula C16H16N5NaO7S2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count8
    Exact Mass477.03888450 g/mol
    Monoisotopic Mass477.03888450 g/mol
    Topological Polar Surface Area230 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity839
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameCefotaxime sodium
    Drug LabelSterile CLAFORAN (cefotaxime sodium) is a semisynthetic, broad spectrum cephalosporin antibiotic for parenteral administration. It is the sodium salt of 7-[2-(2-amino-4-thiazolyl) glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-...
    Active IngredientCefotaxime sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyWockhardt; Hospira; Lupin

    2 of 4  
    Drug NameClaforan
    Drug LabelSterile CLAFORAN (cefotaxime sodium) is a semisynthetic, broad spectrum cephalosporin antibiotic for parenteral administration. It is the sodium salt of 7-[2-(2-amino-4-thiazolyl) glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-...
    Active IngredientCefotaxime sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanySanofi Aventis Us

    3 of 4  
    Drug NameCefotaxime sodium
    Drug LabelSterile CLAFORAN (cefotaxime sodium) is a semisynthetic, broad spectrum cephalosporin antibiotic for parenteral administration. It is the sodium salt of 7-[2-(2-amino-4-thiazolyl) glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-...
    Active IngredientCefotaxime sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyWockhardt; Hospira; Lupin

    4 of 4  
    Drug NameClaforan
    Drug LabelSterile CLAFORAN (cefotaxime sodium) is a semisynthetic, broad spectrum cephalosporin antibiotic for parenteral administration. It is the sodium salt of 7-[2-(2-amino-4-thiazolyl) glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-...
    Active IngredientCefotaxime sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanySanofi Aventis Us

    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
    Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DD - Third-generation cephalosporins

    J01DD01 - Cefotaxime

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    • INJECTABLE;INJECTION - EQ 10GM BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • INJECTABLE;INJECTION - EQ 1GM BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • INJECTABLE;INJECTION - EQ 2GM BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • INJECTABLE;INJECTION - EQ 500MG BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
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