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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H13N8O4S3.Na.5H2O
Molecular Weight 566.565
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFAZOLIN SODIUM PENTAHYDRATE

SMILES

O.O.O.O.O.[Na+].[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN4C=NN=N4)C([O-])=O

InChI

InChIKey=KHQJKXHCWOHDQD-HGUWTHONSA-M
InChI=1S/C14H14N8O4S3.Na.5H2O/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);;5*1H2/q;+1;;;;;/p-1/t9-,12-;;;;;;/m1....../s1

HIDE SMILES / InChI
Cefazolin is a semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cefazolin 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. Cefazolin is used to treat bacterial infections of the skin, moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci species of Gram positive bacteria. This drug also can be used for perioperative prophylaxis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ANCEF

Approved Use

Cefazolin for Injection, USP is indicated in the treatment of the following infections due to susceptible organisms: Respiratory Tract Infections: due to S. penumoniae, S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Injectable benzathine penicillin is considered to be the drug of choice in treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cefazolin for Injection, USP is effective in the eradication of streptococci from the nasopharynx; however, data establishing the efficacy of cefazolin in the subsequent prevention of rheumatic fever are not available. Urinary Tract Infections: due to E. coli, P. mirabilis. Skin and Skin Structure Infections: due to S. aureus (including beta-lactamase-producing strains), S. pyogenes, and other strains of streptococci. Biliary Tract Infections: due to E. coli, various strains of streptococci, P. mirabilis and S. aureus. Bone and Joint Infections: due to S. aureus. Genital Infections: (i.e., prostatitis, epididymitis) due to E. coli, P. mirabilis. Septicemia: due to S. pneumoniae, S. aureus (including beta-lactamase-producing strains), P. mirabilis, E. coli. Endocarditis: due to S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Appropriate culture and susceptibility studies should be performed to determine susceptibility of the causative organism to cefazolin. Perioperative Prophylaxis: The prophylactic administration of Cefazolin for Injection, USP preoperatively, intraoperatively and postoperatively may reduce the incidence of certain postoperative infections in patients undergoing surgical procedures which are classified as contaminated or potentially contaminated (e.g., vaginal hysterectomy, and cholecystectomy in high-risk patients such as those older than 70 years, with acute cholecystitis, obstructive jaundice or common duct bile stones). The perioperative use of Cefazolin for Injection, USP may also be effective in surgical patients in whom infection at the operative site would present a serious risk (e.g., during open-heart surgery and prosthetic arthroplasty). The prophylactic administration of cefazolin should usually be discontinued within a 24 hour period after the surgical procedure. In surgery where the occurrence of infection may be particularly devastating (e.g., open-heart surgery and prosthetic arthroplasty), the prophylactic administration of Cefazolin for Injection, USP may be continued for 3 to 5 days following the completion of surgery. If there are signs of infection, specimens for cultures should be obtained for the identification of the causative organism so that appropriate therapy may be instituted (see DOSAGE AND ADMINISTRATION). To reduce the development of drug-resistant bacteria and maintain the effectiveness of Cefazolin for Injection, USP and other antibacterial drugs, Cefazolin for Injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

1973
Curative
ANCEF

Approved Use

Cefazolin for Injection, USP is indicated in the treatment of the following infections due to susceptible organisms: Respiratory Tract Infections: due to S. penumoniae, S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Injectable benzathine penicillin is considered to be the drug of choice in treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cefazolin for Injection, USP is effective in the eradication of streptococci from the nasopharynx; however, data establishing the efficacy of cefazolin in the subsequent prevention of rheumatic fever are not available. Urinary Tract Infections: due to E. coli, P. mirabilis. Skin and Skin Structure Infections: due to S. aureus (including beta-lactamase-producing strains), S. pyogenes, and other strains of streptococci. Biliary Tract Infections: due to E. coli, various strains of streptococci, P. mirabilis and S. aureus. Bone and Joint Infections: due to S. aureus. Genital Infections: (i.e., prostatitis, epididymitis) due to E. coli, P. mirabilis. Septicemia: due to S. pneumoniae, S. aureus (including beta-lactamase-producing strains), P. mirabilis, E. coli. Endocarditis: due to S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Appropriate culture and susceptibility studies should be performed to determine susceptibility of the causative organism to cefazolin. Perioperative Prophylaxis: The prophylactic administration of Cefazolin for Injection, USP preoperatively, intraoperatively and postoperatively may reduce the incidence of certain postoperative infections in patients undergoing surgical procedures which are classified as contaminated or potentially contaminated (e.g., vaginal hysterectomy, and cholecystectomy in high-risk patients such as those older than 70 years, with acute cholecystitis, obstructive jaundice or common duct bile stones). The perioperative use of Cefazolin for Injection, USP may also be effective in surgical patients in whom infection at the operative site would present a serious risk (e.g., during open-heart surgery and prosthetic arthroplasty). The prophylactic administration of cefazolin should usually be discontinued within a 24 hour period after the surgical procedure. In surgery where the occurrence of infection may be particularly devastating (e.g., open-heart surgery and prosthetic arthroplasty), the prophylactic administration of Cefazolin for Injection, USP may be continued for 3 to 5 days following the completion of surgery. If there are signs of infection, specimens for cultures should be obtained for the identification of the causative organism so that appropriate therapy may be instituted (see DOSAGE AND ADMINISTRATION). To reduce the development of drug-resistant bacteria and maintain the effectiveness of Cefazolin for Injection, USP and other antibacterial drugs, Cefazolin for Injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

1973
Curative
ANCEF

Approved Use

Cefazolin for Injection, USP is indicated in the treatment of the following infections due to susceptible organisms: Respiratory Tract Infections: due to S. penumoniae, S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Injectable benzathine penicillin is considered to be the drug of choice in treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cefazolin for Injection, USP is effective in the eradication of streptococci from the nasopharynx; however, data establishing the efficacy of cefazolin in the subsequent prevention of rheumatic fever are not available. Urinary Tract Infections: due to E. coli, P. mirabilis. Skin and Skin Structure Infections: due to S. aureus (including beta-lactamase-producing strains), S. pyogenes, and other strains of streptococci. Biliary Tract Infections: due to E. coli, various strains of streptococci, P. mirabilis and S. aureus. Bone and Joint Infections: due to S. aureus. Genital Infections: (i.e., prostatitis, epididymitis) due to E. coli, P. mirabilis. Septicemia: due to S. pneumoniae, S. aureus (including beta-lactamase-producing strains), P. mirabilis, E. coli. Endocarditis: due to S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Appropriate culture and susceptibility studies should be performed to determine susceptibility of the causative organism to cefazolin. Perioperative Prophylaxis: The prophylactic administration of Cefazolin for Injection, USP preoperatively, intraoperatively and postoperatively may reduce the incidence of certain postoperative infections in patients undergoing surgical procedures which are classified as contaminated or potentially contaminated (e.g., vaginal hysterectomy, and cholecystectomy in high-risk patients such as those older than 70 years, with acute cholecystitis, obstructive jaundice or common duct bile stones). The perioperative use of Cefazolin for Injection, USP may also be effective in surgical patients in whom infection at the operative site would present a serious risk (e.g., during open-heart surgery and prosthetic arthroplasty). The prophylactic administration of cefazolin should usually be discontinued within a 24 hour period after the surgical procedure. In surgery where the occurrence of infection may be particularly devastating (e.g., open-heart surgery and prosthetic arthroplasty), the prophylactic administration of Cefazolin for Injection, USP may be continued for 3 to 5 days following the completion of surgery. If there are signs of infection, specimens for cultures should be obtained for the identification of the causative organism so that appropriate therapy may be instituted (see DOSAGE AND ADMINISTRATION). To reduce the development of drug-resistant bacteria and maintain the effectiveness of Cefazolin for Injection, USP and other antibacterial drugs, Cefazolin for Injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

1973
Curative
ANCEF

Approved Use

Cefazolin for Injection, USP is indicated in the treatment of the following infections due to susceptible organisms: Respiratory Tract Infections: due to S. penumoniae, S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Injectable benzathine penicillin is considered to be the drug of choice in treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cefazolin for Injection, USP is effective in the eradication of streptococci from the nasopharynx; however, data establishing the efficacy of cefazolin in the subsequent prevention of rheumatic fever are not available. Urinary Tract Infections: due to E. coli, P. mirabilis. Skin and Skin Structure Infections: due to S. aureus (including beta-lactamase-producing strains), S. pyogenes, and other strains of streptococci. Biliary Tract Infections: due to E. coli, various strains of streptococci, P. mirabilis and S. aureus. Bone and Joint Infections: due to S. aureus. Genital Infections: (i.e., prostatitis, epididymitis) due to E. coli, P. mirabilis. Septicemia: due to S. pneumoniae, S. aureus (including beta-lactamase-producing strains), P. mirabilis, E. coli. Endocarditis: due to S. aureus (including beta-lactamase-producing strains) and S. pyogenes. Appropriate culture and susceptibility studies should be performed to determine susceptibility of the causative organism to cefazolin. Perioperative Prophylaxis: The prophylactic administration of Cefazolin for Injection, USP preoperatively, intraoperatively and postoperatively may reduce the incidence of certain postoperative infections in patients undergoing surgical procedures which are classified as contaminated or potentially contaminated (e.g., vaginal hysterectomy, and cholecystectomy in high-risk patients such as those older than 70 years, with acute cholecystitis, obstructive jaundice or common duct bile stones). The perioperative use of Cefazolin for Injection, USP may also be effective in surgical patients in whom infection at the operative site would present a serious risk (e.g., during open-heart surgery and prosthetic arthroplasty). The prophylactic administration of cefazolin should usually be discontinued within a 24 hour period after the surgical procedure. In surgery where the occurrence of infection may be particularly devastating (e.g., open-heart surgery and prosthetic arthroplasty), the prophylactic administration of Cefazolin for Injection, USP may be continued for 3 to 5 days following the completion of surgery. If there are signs of infection, specimens for cultures should be obtained for the identification of the causative organism so that appropriate therapy may be instituted (see DOSAGE AND ADMINISTRATION). To reduce the development of drug-resistant bacteria and maintain the effectiveness of Cefazolin for Injection, USP and other antibacterial drugs, Cefazolin for Injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

1973
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
280.9 μg/mL
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFAZOLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
509.9 μg × h/mL
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFAZOLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.01 h
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFAZOLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 g 2 times / day multiple, intravenous
Studied dose
Dose: 4 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 4 g, 2 times / day
Sources:
healthy, 21 to 35 years
n = 7
Health Status: healthy
Age Group: 21 to 35 years
Sex: M
Population Size: 7
Sources:
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (14.3%)
Sources:
1.5 g 8 times / day multiple, intravenous
Highest studied dose
Dose: 1.5 g, 8 times / day
Route: intravenous
Route: multiple
Dose: 1.5 g, 8 times / day
Sources:
unhealthy, 21-34 years
n = 4
Health Status: unhealthy
Condition: endocarditis
Age Group: 21-34 years
Sex: M+F
Population Size: 4
Sources:
1 g 4 times / day multiple, intravenous
Recommended
Dose: 1 g, 4 times / day
Route: intravenous
Route: multiple
Dose: 1 g, 4 times / day
Sources:
healthy, 75 years
n = 1
Health Status: healthy
Age Group: 75 years
Sex: F
Population Size: 1
Sources:
Other AEs: Pseudomembranous colitis...
Other AEs:
Pseudomembranous colitis
Sources:
1 g 3 times / day multiple, intravenous
Dose: 1 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 1 g, 3 times / day
Sources:
unhealthy
n = 75
Health Status: unhealthy
Condition: closed fractures
Population Size: 75
Sources:
Other AEs: Infection...
Other AEs:
Infection (serious, 15 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Rash 14.3%
Disc. AE
4 g 2 times / day multiple, intravenous
Studied dose
Dose: 4 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 4 g, 2 times / day
Sources:
healthy, 21 to 35 years
n = 7
Health Status: healthy
Age Group: 21 to 35 years
Sex: M
Population Size: 7
Sources:
Pseudomembranous colitis
1 g 4 times / day multiple, intravenous
Recommended
Dose: 1 g, 4 times / day
Route: intravenous
Route: multiple
Dose: 1 g, 4 times / day
Sources:
healthy, 75 years
n = 1
Health Status: healthy
Age Group: 75 years
Sex: F
Population Size: 1
Sources:
Infection serious, 15 patients
1 g 3 times / day multiple, intravenous
Dose: 1 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 1 g, 3 times / day
Sources:
unhealthy
n = 75
Health Status: unhealthy
Condition: closed fractures
Population Size: 75
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 1740 uM]
yes [Ki 180 uM]
yes [Ki 550 uM]
PubMed

PubMed

TitleDatePubMed
Double-blind comparison of phlebitis produced by cefazolin versus cephalothin.
1975 Apr
Double-blind comparison of phlebitis associated with cefazolin and cephalothin.
1976 Jul
Hemolysis induced by cefazolin and cephalothin in a patient with penicillin sensitivity.
1978 May-Jun
Antigenicity of beta-lactam antibiotic preparations: production of IgE antibodies to beta-lactam antibiotic and their cross-reaction within the antibiotic group.
1982
Combination of amikacin and carbenicillin with or without cefazolin as empirical treatment of febrile neutropenic patients. The International Antimicrobial Therapy Project Group of the European Organization for Research and Treatment of Cancer.
1983 Oct
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration].
1988 Jun
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.
2001
Stability of cefazolin sodium in icodextrin-containing peritoneal dialysis solution.
2002 Dec 1
The effect of additives on the crystallization of cefazolin sodium during freeze-drying.
2003 Feb
The vitro efficacy of beta-lactam and beta-lactamase inhibitors against multidrug resistant clinical strains of Mycobacterium tuberculosis.
2004 Apr
The release of cefazolin and gentamicin from biodegradable PLA/PGA beads.
2004 Apr 1
In situ investigation of drug diffusion in hydrogels by the refractive index method.
2004 May 15
Potassium permanganate-glyoxal chemiluminescence system for flow injection analysis of cephalosporin antibiotics: cefalexin, cefadroxil, and cefazolin sodium in pharmaceutical preparations.
2004 Sep 8
Effect of isoniazid on the pharmacodynamics of cefazolin-induced seizures in rats.
2005 Apr
Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1.
2005 Oct 1
Voltammetric behavior and assay of the antibiotic drug cefazolin sodium in bulk form and pharmaceutical formulation at a mercury electrode.
2005 Oct 4
Graft infectivity of rifampin and silver-bonded polyester grafts to MRSA contamination.
2005 Sep-Oct
Infective endocarditis with an aortic periannular abscess extending along the right coronary artery.
2006 Jun
Influence of ascorbic acid on BUN, creatinine, resistive index in canine renal ischemia-reperfusion injury.
2006 Mar
Conventional and dense gas techniques for the production of liposomes: a review.
2008
Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter.
2008 Jun 17
Treatment of sinusitis with corticosteroids in combination with antibiotics in experimentally induced rhinosinusitis.
2008 May
[Retropharyngeal abscesses: a retrospective analysis of 10 patients].
2008 Sep-Oct
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.
2009
[Antibiotic susceptibility of pathogenic bacteria isolated from 893 children with lower respiratory infection in Guiyang].
2009 Dec
Functional recovery and neural differentiation after transplantation of allogenic adipose-derived stem cells in a canine model of acute spinal cord injury.
2009 Dec
Kinetic spectrofluorimetric determination of certain cephalosporins in human plasma.
2009 Feb 15
The effects of methylprednisolone and cefazolin sodium on antioxidant status in experimentally induced maxillary sinusitis.
2009 Oct
Kinetic spectrophotometric determination of certain cephalosporins using oxidized quercetin reagent.
2009 Sep 1
Ectopic intrauterine device in the bladder of a pregnant woman.
2010
Evaluating intra- and inter-examiner reproducibility in histometric measurement: one-wall intrabony periodontal defects in beagle dogs.
2010 Aug
Color selectivity of neurons in the posterior inferior temporal cortex of the macaque monkey.
2010 Jul
Acute osteomyelitis of the acetabulum induced by Staphylococcus capitis in a young athlete.
2010 Jun 18
Osteoid osteoma of the femur in a 7-month-old infant treated with radiofrequency ablation.
2010 Nov
Non-syndromic multiple supernumerary teeth in a family unit with a normal karyotype: case report.
2010 Nov 5
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

Moderate to severe infections: 500 mg to 1 gram, every 6 to 8 hours; mild infections caused by susceptible gram-positive cocci: 250 mg to 500 mg, every 8 hours; acute, uncomplicated urinary tract infections: 1 gram, every 12 hours; Pneumococcal pneumonia: 500 mg, every 12 hours; Severe, life threatening infections (e.g., endocarditis, septicemia): 1 gram to 1.5 grams, every 6 hours
Route of Administration: Other
In Vitro Use Guide
Susceptibilities of 259 isolates of pathogenic bacteria to cefazolin were measured by broth and agar dilution procedures. Beta-hemolytic streptococci were inhibited by 0.25 mug/ml, whereas Staphylococcus aureus and alphahemolytic streptococci were inhibited by 2.0 mug/ml. Enterococci were resistant to less than 32 mug/ml. Wide variation was seen with gram-negative species. Most isolates of Klebsiella species and Proteus mirabilis were inhibited by 4.0 or 8.0 mug/ml. Escherichia coli were less susceptible, and most isolates of Pseudomonas aeruginosa, Serratia species, and Enterobacter species were resistant to 128 mug/ml.
Name Type Language
CEFAZOLIN SODIUM PENTAHYDRATE
Common Name English
CEFAZOLIN SODIUM HYDRATE [JAN]
Common Name English
Cefazolin sodium pentahydrate [WHO-DD]
Common Name English
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, HYDRATE (1:1:5), (6R,7R)-
Common Name English
CEFAZOLIN SODIUM HYDRATE
Common Name English
Code System Code Type Description
CAS
115850-11-8
Created by admin on Sat Dec 16 06:39:20 GMT 2023 , Edited by admin on Sat Dec 16 06:39:20 GMT 2023
PRIMARY
EVMPD
SUB33474
Created by admin on Sat Dec 16 06:39:20 GMT 2023 , Edited by admin on Sat Dec 16 06:39:20 GMT 2023
PRIMARY
SMS_ID
100000127451
Created by admin on Sat Dec 16 06:39:20 GMT 2023 , Edited by admin on Sat Dec 16 06:39:20 GMT 2023
PRIMARY
PUBCHEM
23678598
Created by admin on Sat Dec 16 06:39:20 GMT 2023 , Edited by admin on Sat Dec 16 06:39:20 GMT 2023
PRIMARY
FDA UNII
XLJ4VSY381
Created by admin on Sat Dec 16 06:39:20 GMT 2023 , Edited by admin on Sat Dec 16 06:39:20 GMT 2023
PRIMARY