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Chemistry

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Also known as: 25953-19-9, Cephazolin, Cephamezine, Cefazoline, Cefamezin, Cephazoline
Molecular Formula
C14H14N8O4S3
Molecular Weight
454.5  g/mol
InChI Key
MLYYVTUWGNIJIB-BXKDBHETSA-N
FDA UNII
IHS69L0Y4T

Cefazolin
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.
Cefazolin is a Cephalosporin Antibacterial.
1 2D Structure

Cefazolin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(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-carboxylic acid
2.1.2 InChI
InChI=1S/C14H14N8O4S3/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)/t9-,12-/m1/s1
2.1.3 InChI Key
MLYYVTUWGNIJIB-BXKDBHETSA-N
2.1.4 Canonical SMILES
CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
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
2.2 Other Identifiers
2.2.1 UNII
IHS69L0Y4T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ancef

2. Cefamedin

3. Cefamezine

4. Cefazolin Sodium

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. 25953-19-9

2. Cephazolin

3. Cephamezine

4. Cefazoline

5. Cefamezin

6. Cephazoline

7. Cephazolidin

8. Cefazolin Acid

9. Cefazolina

10. Cefazolinum

11. Cez

12. Kefzol

13. (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-carboxylic Acid

14. J01db04

15. Chebi:474053

16. Ihs69l0y4t

17. Elzogram

18. Cefazina

19. Firmacef

20. Liviclina

21. Atirin

22. Acef

23. (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-carboxylic Acid

24. Ncgc00159465-02

25. Dsstox_cid_2753

26. Sk&f-41558

27. Dsstox_rid_76717

28. Cefazoline [inn-french]

29. Cefazolinum [inn-latin]

30. Dsstox_gsid_22753

31. (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-carboxylic Acid

32. Cefazolina [inn-spanish]

33. Cefazolin (usp)

34. (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-carboxylic Acid

35. Smr000387025

36. Cas-25953-19-9

37. Skf 41558

38. Hsdb 3213

39. Einecs 247-362-8

40. Unii-ihs69l0y4t

41. Brn 4169371

42. Cefazolin [usp:inn:ban]

43. Cefazolin Acid,(s)

44. (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-carboxylic Acid

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

46. 7-(1-(1h-)-tetrazolylacetamido)-3-(2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl)delta3-cephem-4-carboxylic Acid

47. Nsc291561

48. Spectrum_000106

49. Cefazolin [inn]

50. Cefazolin [mi]

51. Cefazolin [hsdb]

52. Prestwick0_000736

53. Prestwick1_000736

54. Prestwick2_000736

55. Prestwick3_000736

56. Spectrum2_001140

57. Spectrum3_000330

58. Spectrum4_000267

59. Spectrum5_000665

60. Cefazolin [vandf]

61. Cefazolinfor Culture Media

62. Cefazolin [mart.]

63. Epitope Id:116197

64. Ec 247-362-8

65. Cefazolin [usp-rs]

66. Cefazolin [who-dd]

67. Schembl2841

68. Chembl1435

69. Lopac0_000274

70. Bspbio_000692

71. Bspbio_001939

72. Kbiogr_000734

73. Kbioss_000546

74. Mls001032060

75. Mls001049010

76. Divk1c_000014

77. Spbio_001039

78. Spbio_002631

79. Bpbio1_000762

80. Dtxsid2022753

81. Gtpl10935

82. Kbio1_000014

83. Kbio2_000546

84. Kbio2_003114

85. Kbio2_005682

86. Kbio3_001159

87. Cefazolin [usp Monograph]

88. Ninds_000014

89. Hms2268d15

90. 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)-

91. Hy-b1892

92. Zinc3830405

93. Tox21_111691

94. Bdbm50370587

95. S5936

96. Akos015962265

97. Tox21_111691_1

98. Db01327

99. Sdccgsbi-0050262.p005

100. Idi1_000014

101. Ncgc00022653-09

102. (6r,7r)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1h-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

103. 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-7beta-[(1h-tetrazol-1-ylacetyl)amino]-3,4-didehydrocepham-4-carboxylic Acid

104. 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)-

105. 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)acetamido)-

106. Ac-16010

107. Bs-52943

108. Sbi-0050262.p004

109. Cs-0013954

110. C06880

111. D02299

112. 953c199

113. A818105

114. Q415739

115. W-107209

116. (6r, 7r)-3-[[(5-methyl-1,3,4-thiadiazol-2- Yl)thio]methyl]-8-oxo-7-[[1h-tetrazol-1- Yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2- Ene-2-carboxylic Acid

117. (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-carboxylic Acid

118. (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-carboxylic Acid;cefazolin Acid

119. (6r,7r)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1h-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

120. 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)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 454.5 g/mol
Molecular Formula C14H14N8O4S3
XLogP3-0.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass454.03001448 g/mol
Monoisotopic Mass454.03001448 g/mol
Topological Polar Surface Area235 Ų
Heavy Atom Count29
Formal Charge0
Complexity740
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 Information
1 of 2  
Drug NameKefzol
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar

2 of 2  
Drug NameKefzol
Active IngredientCefazolin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 500mg base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar

4.2 Therapeutic Uses

Mesh Heading: anti-bacterial agents

National Library of Medicine, SIS; ChemIDplus Record for Cefazolin (25953-19-9). Available from, as of April 14, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp


Cephalosporins

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Cefazolin is indicated in the treatment of biliary tract infections caused by susceptible organisms. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 821


THERAP CAT: Antibacterial.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 326


For more Therapeutic Uses (Complete) data for CEFAZOLIN (17 total), please visit the HSDB record page.


4.3 Drug Warning

Hypersensitivity reactions to cephalosporins are the most common side effects ... /and/ appear to be identical to those caused by the penicillins ... Patients who are allergic to one class of agents may manifest cross-reactivity when a member of the other class is admin. Immunological studies have demonstrated cross-reactivity in as many as 20% of patients who are allergic to penicillin, but clinical studies indicate a much lower frequency (about 1%) ... There are no skin tests that can reliably predict whether a patient will manifest an allergic reaction to the cephalosporins. /Cephalosporins/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1212


Maternal Medication usually Compatible with Breast-Feeding: Cefazolin: Reported Sign or Symptom in Infant or Effect on Lactation: None. /From table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 140 (1994)


Positive direct and indirect antiglobulin (Coombs') test results have been reported in 3% or more of patients receiving a cephalosporin. The mechanism of this reaction is usually nonimmunologic in nature; a cephalosporin-globulin complex coats the erythrocytes and reacts nonspecifically with Coombs' serum. Nonimmunologic positive Coombs' test results are most likely to occur in patients who have received large doses of a cephalosporin or who have impaired renal function or hypoalbuminemia. /Cephalosporins/

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 86


A positive Coombs reaction appears frequently in patients who receive large doses of a cephalosporin. Hemolysis is not usually associated with this phenomenon, although it has been reported. Cephalosporins have produced rare instances of bone-marrow depression, characterized by granulocytopenia ... Serious bleeding related either to ... thrombocytopenia, and/or platelet dysfunction has been reported with several beta-lactam antibiotics. This appears to be a particular problem with certain patients (elderly, poorly nourished, or those with renal insufficiency) who are receiving moxalactam. /Cephalosporins/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1212


For more Drug Warnings (Complete) data for CEFAZOLIN (38 total), please visit the HSDB record page.


4.4 Drug Indication

Mainly used to treat bacterial infections of the skin. It can also be used to treat moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, heart valve, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci species of Gram positive bacteria. May be used for surgical prophylaxis; if required metronidazole may be added to cover B. fragilis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefazolin (also known as cefazoline or cephazolin) is a semi-synthetic first generation cephalosporin for parenteral administration. Cefazolin has broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CEFAZOLIN
5.3.2 FDA UNII
IHS69L0Y4T
5.3.3 Pharmacological Classes
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
5.4 ATC Code

J01DB04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DB - First-generation cephalosporins

J01DB04 - Cefazolin


5.5 Absorption, Distribution and Excretion

Absorption

Not absorbed from GI tract. Must be administered parenterally. Peak serum concentrations attained 1-2 hours post intramuscular injection.


Route of Elimination

Cefazolin is present in very low concentrations in the milk of nursing mothers. Cefazolin is excreted unchanged in the urine. In the first six hours approximately 60% of the drug is excreted in the urine and this increases to 70%-80% within 24 hours.


CEFAZOLIN CROSSES INFLAMED SYNOVIAL MEMBRANES, YIELDING SYNOVIAL FLUID ANTIBIOTIC CONCN GREATER THAN THOSE IN SERUM WITHIN 2 HR OF IM DOSE... CLEARANCE OF CEFAZOLIN BY KIDNEY IS PREDOMINANTLY BY GLOMERULAR FILTRATION, & CLEARANCE RATES ARE LINEARLY RELATED TO CREATININE CLEARANCE...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 176


CEFAZOLIN RAPIDLY PENETRATES BODY TISSUES IN RATS, & DECLINE OF TISSUE ANTIBIOTIC LEVELS AFTER DOSING IS FIRST-ORDER. VERY SMALL AMT OF DRUG CROSS BLOOD-BRAIN BARRIER & PLACENTAL TRANSFER APPEARS NEGLIGIBLE...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 176


...DURING STUDIES OF CEFAZOLIN TRANSFERENCE IN MAN, 92-100% OF ADMIN DOSE WAS ACCOUNTED FOR BY URINARY EXCRETION...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 106


... About 80% of cefazolin is reversibly bound to plasma protein ... is excreted in bile even when there is gallbladder disease ... concn may normally exceed that in plasma by 3 times.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161


For more Absorption, Distribution and Excretion (Complete) data for CEFAZOLIN (13 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Not metabolized.


Metabolism of cefazolin is very limited in most of the animal species tested and in /humans/. After parenteral administration of cefazolin nearly 100% is excreted unchanged in urine with 24 hours in /humans/, dog and horse. No major metabolites seem to occur.

European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products; Cefazolin, Summary Report. EMEA/MRL/0126/96-Final (July 1996). Available from, as of July 21, 2006: https://www.ema.europa.eu/ema/index.jsp?curl=pages/document_library/landing/document_library_search.jsp&murl=menus/document_library/document_library.jsp&mid


5.7 Biological Half-Life

The serum half-life is approximately 1.8 hours following IV administration and approximately 2.0 hours following IM administration.


The serum half-life of cefazolin is 1.2-2.2 hr in adults with normal renal function. In one study, half-life was 6.8 hr in 1 adult with a creatinine clearance of 26 ml/min, 12 hr in 3 adults with creatinine clearances of 12-17 ml/min, and 57 hr in 3 adults with creatinine clearances less than 5 ml/min.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 93


5.8 Mechanism of Action

In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.


Bactericidal; action depends on ability to reach and bind penicillin-binding proteins located in bacterial cytoplasmic membranes; cephalosporins inhibit bacterial septum and cell wall synthesis, probably by acylation of membrane-bound transpeptidase enzymes. This prevents cross-linkage of peptidoglycan chains, which is necessary for bacterial cell wall strength and rigidity. Also, cell division and growth are inhibited, and lysis and elongation of susceptible bacteria frequently occur. Rapidly dividing bacteria are those most susceptible to the action of cephalosporins. /Cephalosporins/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 822


API Reference Price

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09-Feb-2021
23-Oct-2024
KGS
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Average Price (USD/KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

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