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Chemistry

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Also known as: Cefazolin sodium salt, 27164-46-1, Cefazoline sodium, Ancef, Cefazil, Totacef
Molecular Formula
C14H13N8NaO4S3
Molecular Weight
476.5  g/mol
InChI Key
FLKYBGKDCCEQQM-WYUVZMMLSA-M
FDA UNII
P380M0454Z

Cefazolin Sodium
A semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.
1 2D Structure

Cefazolin Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C14H14N8O4S3.Na/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21;/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26);/q;+1/p-1/t9-,12-;/m1./s1
2.1.3 InChI Key
FLKYBGKDCCEQQM-WYUVZMMLSA-M
2.1.4 Canonical SMILES
CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)[O-].[Na+]
2.1.5 Isomeric SMILES
CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)[O-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
P380M0454Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ancef

2. Cefamedin

3. Cefamezine

4. Cefazolin

5. Cephamezine

6. Cephazolin

7. Cephazolin Sodium

8. Cephazolin, Sodium

9. Gramaxin

10. Kefzol

11. Sodium Cephazolin

12. Sodium, Cefazolin

13. Sodium, Cephazolin

14. Totacef

2.3.2 Depositor-Supplied Synonyms

1. Cefazolin Sodium Salt

2. 27164-46-1

3. Cefazoline Sodium

4. Ancef

5. Cefazil

6. Totacef

7. Kefzol

8. Sodium Cephazolin

9. Cefamedin

10. Gramaxin

11. Zolicef

12. Sodium Cefazolin

13. Cefacidal

14. Cephazolin Sodium

15. Cefazolin (sodium)

16. Monosodium Cefazolin

17. Sk&f 41558

18. Cefazolin Injection

19. Cefazolin And Dextrose

20. Cefazina

21. Firmacef

22. Liviclina

23. Atirin

24. Acef

25. Chebi:3483

26. Mls000028706

27. Nsc-291561

28. P380m0454z

29. Biazolina

30. Smr000058708

31. Skf 41558

32. Sk&f-41558

33. Sodium Cez

34. Cefazolin Sodium 100 Microg/ml In Acetonitrile/water

35. Ancef In Plastic Container

36. Cefabiozim

37. Cefalomicina

38. Lampocef

39. Neofazol

40. Zolisint

41. Recef

42. Zolin

43. Bor-cefazol

44. Cez Sodium

45. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1h-tetrazol-1-yl)acetyl)amino)-, Monosodium Salt (6r-trans)-

46. Monosodium (6r,7r)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1h-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

47. Lilly 46083

48. Unii-p380m0454z

49. Cefazolin Sodium [usan:usp:jan]

50. Sodium;(6r,7r)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

51. Prestwick_975

52. Einecs 248-278-4

53. Monosodium Cephazolin

54. Mfcd00056883

55. Ancef (tn)

56. Nsc 291561

57. Opera_id_1323

58. Ancef In Dextrose 5% In Plastic Container

59. Schembl40735

60. Spectrum1500164

61. Cefazolin Sodium [jan]

62. Cefazolin Sodium (jp17/usp)

63. Sodium Cez; Skf-41558

64. Cefazolin Sodium [usan]

65. Cefazolin Sodium [vandf]

66. Chembl1200523

67. Hms500a16

68. Ancef In Sodium Chloride 0.9% In Plastic Container

69. Cefazolin Sodium [mart.]

70. Cefazolin Sodium [who-dd]

71. Dtxsid901015786

72. Hms1570c14

73. Hms1920k07

74. Hms2091a10

75. Hms2097c14

76. Hms2230i22

77. Hms3260h10

78. Hms3714c14

79. Cefazolin Sodium Salt [mi]

80. Hy-b1078

81. Tox21_500274

82. Bdbm50247885

83. Ccg-40011

84. S4595

85. Akos015895533

86. Cefazolin Sodium [orange Book]

87. Cefazolin Sodium [ep Monograph]

88. Cs-4634

89. Lp00274

90. Cefazolin Sodium [usp Monograph]

91. Cefazolin Sodium Salt, 89.1-110.1%

92. Ncgc00093731-01

93. Ncgc00260959-01

94. 3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-7-(2-(1h-tetrazol-1-yl)acetamido)-3-cephem-4-carboxylate

95. Ac-13166

96. Ac-31729

97. As-12230

98. Sodium (6r,7r)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1h-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

99. Eu-0100274

100. C 5020

101. C-2465

102. C08098

103. D00905

104. Q27106104

105. Cefazolin Sodium Salt, Antibiotic For Culture Media Use Only

106. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1h-tetrazol-1-yl)acetyl)amino)-, (6r-trans)-, Sodium Salt

107. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1h-tetrazol-1-yl)acetyl]amino]-, Sodium Salt, (6r,7r)- (1:1)

108. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1h-tetrazol-1-yl)acetyl]amino]-,(6r,7r)-,sodium

109. Sodium (6r,7r)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1h-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

110. Sodium (6r,7r)-7-(2-(1h-tetrazol-1-yl)acetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

111. Sodium (6r,7r)-7-(2-(1h-tetrazol-1-yl)acetamido)-3-((5-methyl-1,3,4-thiadiazol-2-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

112. Sodium (6r-trans)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(1h-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

113. Sodium 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-7beta-[(1h-tetrazol-1-ylacetyl)amino]-3,4-didehydrocepham-4-carboxylate

114. Sodium 7beta-(1h-tetrazol-1-yl)acetamido-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate

115. Sodium 7beta-[2-(1h-tetrazol-1-yl)-acetamido]-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate

116. Sodium 7beta-[2-(1h-tetrazol-1-yl)acetamido]-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 476.5 g/mol
Molecular Formula C14H13N8NaO4S3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass476.01195873 g/mol
Monoisotopic Mass476.01195873 g/mol
Topological Polar Surface Area238 Ų
Heavy Atom Count30
Formal Charge0
Complexity746
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameAncef in plastic container
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 20mg base/ml; eq 10mg base/ml
Market StatusPrescription
CompanyBaxter Hlthcare

2 of 8  
Drug NameCefazolin and dextrose
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyB Braun

3 of 8  
Drug NameCefazolin sodium
Drug LabelCEFAZOLIN FOR INJECTION is a semi-synthetic cephalosporin for parenteral administration. It is the sodium salt of 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]-methyl}-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxy...
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 20gm base/vial; eq 100gm base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 300gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar; Hospira; Steri Pharma; Hikma Farmaceutica; Samson Medcl; Sandoz

4 of 8  
Drug NameKefzol
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar

5 of 8  
Drug NameAncef in plastic container
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 20mg base/ml; eq 10mg base/ml
Market StatusPrescription
CompanyBaxter Hlthcare

6 of 8  
Drug NameCefazolin and dextrose
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyB Braun

7 of 8  
Drug NameCefazolin sodium
Drug LabelCEFAZOLIN FOR INJECTION is a semi-synthetic cephalosporin for parenteral administration. It is the sodium salt of 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]-methyl}-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxy...
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 20gm base/vial; eq 100gm base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 300gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar; Hospira; Steri Pharma; Hikma Farmaceutica; Samson Medcl; Sandoz

8 of 8  
Drug NameKefzol
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar

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]

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28-Jan-2021
23-Sep-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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USFDA APPLICATION NUMBER - 207131

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