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2D Structure
Also known as: Sodium cefuroxime, Zinacef, Cefuroxime sodium salt, Biociclin, 56238-63-2, Anaptivan
Molecular Formula
C16H15N4NaO8S
Molecular Weight
446.4  g/mol
InChI Key
URDOHUPGIOGTKV-JTBFTWTJSA-M
FDA UNII
R8A7M9MY61

Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, GONORRHEA, and HAEMOPHILUS.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C16H16N4O8S.Na/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20;/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24);/q;+1/p-1/b19-9-;/t10-,14-;/m1./s1
2.1.3 InChI Key
URDOHUPGIOGTKV-JTBFTWTJSA-M
2.1.4 Canonical SMILES
CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)[O-].[Na+]
2.1.5 Isomeric SMILES
CO/N=C(/C1=CC=CO1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)[O-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
R8A7M9MY61
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cefuroxime

2. Cephuroxime

3. Ketocef

4. Zinacef

2.3.2 Depositor-Supplied Synonyms

1. Sodium Cefuroxime

2. Zinacef

3. Cefuroxime Sodium Salt

4. Biociclin

5. 56238-63-2

6. Anaptivan

7. Kefurox

8. Cefuroxime (sodium)

9. Cefumax

10. Cefurex

11. Medoxim

12. Kesint

13. Chebi:3517

14. R8a7m9my61

15. Colifossim

16. Sodium (6r,7r)-7-(2-(2-furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7(sup 2)-(z)-(o-methyloxime), Carbamate (ester)

17. Spectrazolr

18. Bioxima

19. Cefofix

20. Curoxim

21. Curoxima

22. Curoxime

23. Furoxil

24. Ketocef

25. Ultroxim

26. Cefuroxim Hexal

27. Cefuroxim Lilly

28. Cefuroxima Fabra

29. Cefuroxim Aj

30. Cefuroxim Mn

31. Cefuroxim Curasan

32. Cefuroxima Richet

33. Cetroxil [inj.]

34. Cefuroxim Fresenius

35. Cefuroxim Genericsn

36. Froxal [inj.]

37. Sharox [inj.]

38. Zinnat [inj.]

39. Cetroxil

40. Froxal

41. Cefuroxim Norcox

42. Cefuroxim Norcox [inj.]

43. Cefuroxime Na

44. Kefurox In Plastic Container

45. Zinacef In Plastic Container

46. Zinacef (tn)

47. Einecs 260-073-1

48. Cefuroxime And Dextrose In Duplex Container

49. Unii-r8a7m9my61

50. Mls000069576

51. Cefuroxime Sodium [usp:ban:jan]

52. Cefuroxime For Injection And Dextrose For Injection In Duplex Container

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

54. Ks-1040

55. Smr000058808

56. Mls001332625

57. Mls001332626

58. Sodium (6r-(6alpha,7beta(z)))-3-(((aminocarbonyl)oxy)methyl)-7-(2-furyl(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

59. Cefuroxime Sodium (jan/usp)

60. Schembl719536

61. Cefuroxime Sodium [jan]

62. Chembl2146124

63. Cefuroxime Sodium [vandf]

64. Cefuroxime Sodium [mart.]

65. Dtxsid201015616

66. Hms2097o21

67. Hms3714o21

68. Cefuroxime Sodium [usp-rs]

69. Cefuroxime Sodium [who-dd]

70. Cefuroxime Sodium Salt [mi]

71. Hy-b1256

72. Mfcd09878727

73. S4620

74. Akos015961772

75. Ccg-220720

76. Cefuroxime Sodium [ep Impurity]

77. Cefuroxime Sodium [orange Book]

78. Cs-4733

79. Nsc 758166

80. Cefuroxime Sodium [ep Monograph]

81. Cefuroxime Sodium [usp Impurity]

82. Cefuroxime Sodium [usp Monograph]

83. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-, Monosodium Salt (6r-(6alpha,7beta(z)))-

84. Ac-15028

85. C08108

86. D00915

87. Cefuroxime Sodium 100 Microg/ml In Acetonitrile/water

88. Cefuroxime Sodium 100 Microg/ml In Acetonitrile:water

89. Cefuroxime Sodium, European Pharmacopoeia (ep) Reference Standard

90. Cefuroxime Sodium, United States Pharmacopeia (usp) Reference Standard

91. (6r,7r)-3-(carbamoyloxymethyl)-7-[[(2z)-2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

92. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-, Monosodium Salt (6r-(6.alpha.,7.beta.(z)))-

93. Sodium (6r,7r)-3-(carbamoyloxymethyl)-7-((e)-2-(furan-2-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 446.4 g/mol
Molecular Formula C16H15N4NaO8S
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count8
Exact Mass446.05082891 g/mol
Monoisotopic Mass446.05082891 g/mol
Topological Polar Surface Area202 Ų
Heavy Atom Count30
Formal Charge0
Complexity804
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 6  
Drug NameCefuroxime and dextrose in duplex container
Active IngredientCefuroxime sodium
Dosage FormInjectable
RouteInjection
Strengtheq 750mg base/vial; eq 1.5gm base/vial
Market StatusPrescription
CompanyB Braun

2 of 6  
Drug NameCefuroxime sodium
Active IngredientCefuroxime sodium
Dosage FormInjectable
RouteIntramuscular, intravenous; Im-iv; Injection
Strengtheq 750mg base/vial; eq 7.5gm base/vial; eq 1.5gm base/vial
Market StatusPrescription
CompanyTeva Pharms; Hospira; Steri Pharma; Hikma Farmaceutica

3 of 6  
Drug NameZinacef in plastic container
Drug LabelCefuroxime is a sterile semisynthetic, broad-spectrum, cephalosporin antibiotic for parenteral administration. It is the sodium salt of (6R, 7R)-3-carbamoyloxymethyl-7-[Z-2-methoxyimino-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylate, and it has the fo...
Active IngredientCefuroxime sodium
Dosage FormInjectable
RouteInjection
Strengtheq 30mg base/ml
Market StatusPrescription
CompanyCovis Injectables

4 of 6  
Drug NameCefuroxime and dextrose in duplex container
Active IngredientCefuroxime sodium
Dosage FormInjectable
RouteInjection
Strengtheq 750mg base/vial; eq 1.5gm base/vial
Market StatusPrescription
CompanyB Braun

5 of 6  
Drug NameCefuroxime sodium
Active IngredientCefuroxime sodium
Dosage FormInjectable
RouteIntramuscular, intravenous; Im-iv; Injection
Strengtheq 750mg base/vial; eq 7.5gm base/vial; eq 1.5gm base/vial
Market StatusPrescription
CompanyTeva Pharms; Hospira; Steri Pharma; Hikma Farmaceutica

6 of 6  
Drug NameZinacef in plastic container
Drug LabelCefuroxime is a sterile semisynthetic, broad-spectrum, cephalosporin antibiotic for parenteral administration. It is the sodium salt of (6R, 7R)-3-carbamoyloxymethyl-7-[Z-2-methoxyimino-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylate, and it has the fo...
Active IngredientCefuroxime sodium
Dosage FormInjectable
RouteInjection
Strengtheq 30mg base/ml
Market StatusPrescription
CompanyCovis Injectables

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]