Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H13N8O4S3.Na |
Molecular Weight | 476.489 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN4C=NN=N4)C([O-])=O
InChI
InChIKey=FLKYBGKDCCEQQM-WYUVZMMLSA-M
InChI=1S/C14H14N8O4S3.Na/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21;/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26);/q;+1/p-1/t9-,12-;/m1./s1
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 Date1973 |
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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 Date1973 |
|||
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 Date1973 |
|||
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 Date1973 |
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 |
---|---|---|
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins. | 1990 |
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Comparison of in vitro antimicrobial susceptibilities of Mycobacterium avium-M. intracellulare strains from patients with acquired immunodeficiency syndrome (AIDS), patients without AIDS, and animal sources. | 1990 Jul |
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Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children. | 2001 |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | 2001 Sep-Oct |
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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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Stability of three cephalosporin antibiotics in AutoDose Infusion System bags. | 2002 May-Jun |
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The vitro efficacy of beta-lactam and beta-lactamase inhibitors against multidrug resistant clinical strains of Mycobacterium tuberculosis. | 2004 Apr |
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The release of cefazolin and gentamicin from biodegradable PLA/PGA beads. | 2004 Apr 1 |
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Antitumor activity of common antibiotics against superficial bladder cancer. | 2004 Mar |
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In situ investigation of drug diffusion in hydrogels by the refractive index method. | 2004 May 15 |
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Chemiluminescence flow-injection analysis of beta-lactam antibiotics using the luminol-permanganate reaction. | 2006 Jul-Aug |
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Infective endocarditis with an aortic periannular abscess extending along the right coronary artery. | 2006 Jun |
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Influence of ascorbic acid on BUN, creatinine, resistive index in canine renal ischemia-reperfusion injury. | 2006 Mar |
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Novel purification strategy for human PON1 and inhibition of the activity by cephalosporin and aminoglikozide derived antibiotics. | 2006 May |
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[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 |
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Treatment of sinusitis with corticosteroids in combination with antibiotics in experimentally induced rhinosinusitis. | 2008 May |
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Functional recovery and neural differentiation after transplantation of allogenic adipose-derived stem cells in a canine model of acute spinal cord injury. | 2009 Dec |
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Kinetic spectrophotometric determination of certain cephalosporins using oxidized quercetin reagent. | 2009 Sep 1 |
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Evaluating intra- and inter-examiner reproducibility in histometric measurement: one-wall intrabony periodontal defects in beagle dogs. | 2010 Aug |
|
Stability of fortified cefazolin ophthalmic solutions prepared in artificial tears containing surfactant-based versus oxidant-based preservatives. | 2010 Oct |
|
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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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C357
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CHEMBL1435
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291561
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P380M0454Z
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23675322
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P380M0454Z
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3483
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DTXSID901015786
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C47968
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248-278-4
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474053
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m3188
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DBSALT000310
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100000090010
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203171
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SUB01107MIG
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27164-46-1
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ACTIVE MOIETY
SUBSTANCE RECORD