Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H14N8O4S3 |
Molecular Weight | 454.507 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN4C=NN=N4)C(O)=O
InChI
InChIKey=MLYYVTUWGNIJIB-BXKDBHETSA-N
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3266730 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | ANCEF Approved UseCefazolin 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 Date1.18540796E11 |
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Curative | ANCEF Approved UseCefazolin 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 Date1.18540796E11 |
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Curative | ANCEF Approved UseCefazolin 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 Date1.18540796E11 |
|||
Curative | ANCEF Approved UseCefazolin 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 Date1.18540796E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... |
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... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
Double-blind comparison of phlebitis associated with cefazolin and cephalothin. | 1976 Jul |
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IgE antibodies for penicillins and cephalosporins in rats. III. Antigenic specificity of rat anti-cephalosporin-OvA IgE sera. | 1981 Jan |
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Antigenicity of beta-lactam antibiotic preparations: production of IgE antibodies to beta-lactam antibiotic and their cross-reaction within the antibiotic group. | 1982 |
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Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins. | 1990 |
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Low convulsive activity of a new carbapenem antibiotic, DK-35C, as compared with existing congeners. | 1999 Nov 5 |
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Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children. | 2001 |
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Use of charge-transfer complexation in the spectrophotometric analysis of certain cephalosporins. | 2001 Jul 6 |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Stability of cefazolin sodium in icodextrin-containing peritoneal dialysis solution. | 2002 Dec 1 |
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Differences in neutrophil death among beta-lactam antibiotics after in vitro killing of bacteria. | 2002 Jul |
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Effect of water content on the solid-state stability in two isomorphic clathrates of cephalosporin: cefazolin sodium pentahydrate (alpha form) and FK041 hydrate. | 2002 Jun |
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beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 2002 Nov |
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The effect of additives on the crystallization of cefazolin sodium during freeze-drying. | 2003 Feb |
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The effects of some antibiotics on sheep lens glucose 6-phosphate dehydrogenase in vitro. | 2003 Mar |
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Antibiotic activity and synergistic effect of antimicrobial peptide against pathogens from a patient with gallstones. | 2004 Aug 27 |
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Efficacy of a non-vancomycin-based peritoneal dialysis peritonitis protocol. | 2005 Apr |
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Effect of isoniazid on the pharmacodynamics of cefazolin-induced seizures in rats. | 2005 Apr |
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[Sensitivity of nanoparticlized cefazolin sodium to the bacteria in vitro]. | 2005 Jun |
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Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. | 2005 Oct 1 |
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Stability of cefazolin sodium in four heparinized and non-heparinized dialysate solutions at 38 degrees C. | 2006 Sep-Oct |
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[Simultaneous spectrophotometric determination of certain beta-lactam antibiotics in rabbit serum using multivariate calibration methods]. | 2007 Feb |
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Conventional and dense gas techniques for the production of liposomes: a review. | 2008 |
|
[Physical and chemical characteristics of a new cefazolin sodium hydrate crystal]. | 2008 Aug |
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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 |
|
Trends in antibacterial use in US academic health centers: 2002 to 2006. | 2008 Nov 10 |
|
[Retropharyngeal abscesses: a retrospective analysis of 10 patients]. | 2008 Sep-Oct |
|
[Antibiotic susceptibility of pathogenic bacteria isolated from 893 children with lower respiratory infection in Guiyang]. | 2009 Dec |
|
Reactive astrocytes in glial scar attract olfactory ensheathing cells migration by secreted TNF-alpha in spinal cord lesion of rat. | 2009 Dec 3 |
|
Color selectivity of neurons in the posterior inferior temporal cortex of the macaque monkey. | 2010 Jul |
|
Osteoid osteoma of the femur in a 7-month-old infant treated with radiofrequency ablation. | 2010 Nov |
|
Sensitive chemiluminescence determination of thirteen cephalosporin antibiotics with luminol-copper(II) reaction. | 2010 Oct |
|
Piezoelectric immunosensors for the detection of individual antibiotics and the total content of penicillin antibiotics in foodstuffs. | 2014 Mar |
|
Investigation of the effects of some drugs and phenolic compounds on human dihydrofolate reductase activity. | 2015 Mar |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4451358
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.
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N0000011161
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NBK548358
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N0000011161
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NBK547862
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N0000011161
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N0000011161
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N0000011161
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WHO-ESSENTIAL MEDICINES LIST |
6.2.1
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NDF-RT |
N0000011161
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WHO-ATC |
J01DB04
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N0000011161
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NCI_THESAURUS |
C357
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N0000175488
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N0000011161
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N0000011161
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NBK548666
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WHO-VATC |
QJ51DB04
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NDF-RT |
N0000011161
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N0000011161
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N0000011161
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QJ01DB04
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1097603
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474053
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530
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CHEMBL1435
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C28913
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CEFAZOLIN
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33255
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Cefazolin
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2180
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D002437
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247-362-8
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DTXSID2022753
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25953-19-9
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SUB07379MIG
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DB01327
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IHS69L0Y4T
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2991
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M3188
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3213
Created by
admin on Fri Dec 16 16:50:17 UTC 2022 , Edited by admin on Fri Dec 16 16:50:17 UTC 2022
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IHS69L0Y4T
Created by
admin on Fri Dec 16 16:50:17 UTC 2022 , Edited by admin on Fri Dec 16 16:50:17 UTC 2022
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PRIMARY |
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