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Chemistry

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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

Cefotaxime
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


API Reference Price

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01-Jan-2021
13-Sep-2024
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