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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20N2.C14H14N8O4S3
Molecular Weight 694.855
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFAZOLIN BENZATHINE

SMILES

c1ccc(cc1)CNCCNCc2ccccc2.Cc1nnc(SCC2=C(C(=O)O)N3C(=O)[C@]([H])([C@@]3([H])SC2)N=C(Cn4cnnn4)O)s1

InChI

InChIKey=YPRSMYNNJOVKFP-GLOBUBTCSA-N
InChI=1S/C16H20N2.C14H14N8O4S3/c1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16;1-6-17-18-14(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/h1-10,17-18H,11-14H2;5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t;9-,12-/m.1/s1

HIDE SMILES / InChI

Molecular Formula C14H14N8O4S3
Molecular Weight 454.511
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C16H20N2
Molecular Weight 240.344
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1.18540796E11
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

1.18540796E11
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

1.18540796E11
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

1.18540796E11
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
Antigenicity of beta-lactam antibiotic preparations: production of IgE antibodies to beta-lactam antibiotic and their cross-reaction within the antibiotic group.
1982
Cephalosporin-induced cholestatic jaundice.
1982 Aug 7
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.
1990
Low convulsive activity of a new carbapenem antibiotic, DK-35C, as compared with existing congeners.
1999 Nov 5
Amykacin-related apneic episode in an infant on peritoneal dialysis.
2000 Apr
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.
2001
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Stability of three cephalosporin antibiotics in AutoDose Infusion System bags.
2002 May-Jun
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Potassium permanganate-glyoxal chemiluminescence system for flow injection analysis of cephalosporin antibiotics: cefalexin, cefadroxil, and cefazolin sodium in pharmaceutical preparations.
2004 Sep 8
Efficacy of a non-vancomycin-based peritoneal dialysis peritonitis protocol.
2005 Apr
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
Kinetic spectrophotometric determination of certain cephalosporins using oxidized quercetin reagent.
2009 Sep 1
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:19:16 UTC 2021
Edited
by admin
on Fri Jun 25 23:19:16 UTC 2021
Record UNII
BJN67HUZ04
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFAZOLIN BENZATHINE
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-((1H-TETRAZOL-1-YLACETYL)AMINO)-, (6R-TRANS)-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)
Common Name English
CEFAZOLIN BENZATHINE [WHO-DD]
Common Name English
CEFAZOLINE BENZATHINE
Common Name English
Code System Code Type Description
EPA CompTox
63307-59-5
Created by admin on Fri Jun 25 23:19:16 UTC 2021 , Edited by admin on Fri Jun 25 23:19:16 UTC 2021
PRIMARY
EVMPD
SUB01108MIG
Created by admin on Fri Jun 25 23:19:16 UTC 2021 , Edited by admin on Fri Jun 25 23:19:16 UTC 2021
PRIMARY
CAS
63307-59-5
Created by admin on Fri Jun 25 23:19:16 UTC 2021 , Edited by admin on Fri Jun 25 23:19:16 UTC 2021
PRIMARY
PUBCHEM
71300925
Created by admin on Fri Jun 25 23:19:16 UTC 2021 , Edited by admin on Fri Jun 25 23:19:16 UTC 2021
PRIMARY
FDA UNII
BJN67HUZ04
Created by admin on Fri Jun 25 23:19:16 UTC 2021 , Edited by admin on Fri Jun 25 23:19:16 UTC 2021
PRIMARY
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