Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H17N3O7S2 |
Molecular Weight | 427.452 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@]2(NC(=O)CC3=CC=CS3)OC)C(O)=O
InChI
InChIKey=WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
Molecular Formula | C16H17N3O7S2 |
Molecular Weight | 427.452 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB01331Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/cefoxitin.html
Sources: http://www.drugbank.ca/drugs/DB01331
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/cefoxitin.html
Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. It is active against a broad range of gram-negative bacteria including anaerobes. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria. The bactericidal action of cefoxitin results from inhibition of cell wall synthesis.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Escherichia coli growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/2663161 |
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Target ID: Klebsiella pneumoniae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/2663161 |
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Target ID: P08506 Gene ID: 945455.0 Gene Symbol: dacC Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331 |
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Target ID: P0AEB2 Gene ID: 945222.0 Gene Symbol: dacA Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331 |
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Target ID: P0AFI5 Gene ID: 946662.0 Gene Symbol: pbpG Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331 |
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Target ID: P02919 Gene ID: 944843.0 Gene Symbol: mrcB Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331 |
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Target ID: P0A3M6 Gene ID: 933948.0 Gene Symbol: penA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) Sources: http://www.drugbank.ca/drugs/DB01331 |
8.0 nM [IC50] | ||
Target ID: Q8DR59 Gene ID: 934791.0 Gene Symbol: pbpA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421 |
6.8 nM [IC50] | ||
Target ID: 933569.0 Gene Symbol: pbp2a Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421 |
2.4 nM [IC50] | ||
Target ID: 934893.0 Gene Symbol: pbp1b Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421 |
0.145 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Cefoxitin Approved UseCefoxitin for Injection, USP is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms in the diseases listed below.
(1) Lower respiratory tract infections, including pneumonia and lung abscess, caused by Streptococcus pneumoniae, other streptococci (excluding enterococci, e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, Haemophilus influenzae, and Bacteroides species.
(2) Urinary tract infections caused by Escherichia coli, Klebsiella species, Proteus mirabilis, Morganella morganii, Proteus vulgaris and Providencia species (including P. rettgeri).
(3) Intra-abdominal infections, including peritonitis and intra-abdominal abscess, caused by Escherichia coli, Klebsiella species, Bacteroides species including Bacteroides fragilis, and Clostridium species.
(4) Gynecological infections, including endometritis, pelvic cellulitis, and pelvic inflammatory disease caused by Escherichia coli, Neisseria gonorrhoeae (including penicillinase-producing strains), Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, Peptostreptococcus species and Streptococcus agalactiae. Cefoxitin for injection, like cephalosporins, has no activity against Chlamydia trachomatis. Therefore, when Cefoxitin for injection is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added.
(5) Septicemia caused by Streptococcus pneumoniae, Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, and Bacteroides species including B. fragilis.
(6) Bone and joint infections caused by Staphylococcus aureus (including penicillinase-producing strains).
(7) Skin and skin structure infections caused by Staphylococcus aureus (including penicillinase-producing strains), Staphylococcus epidermidis, Streptococcus pyogenes and other streptococci (excluding enterococci e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Escherichia coli, Proteus mirabilis, Klebsiella species, Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, and Peptostreptococcus species. Launch Date1.26826565E12 |
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Curative | Cefoxitin Approved UseCefoxitin for Injection, USP is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms in the diseases listed below.
(1) Lower respiratory tract infections, including pneumonia and lung abscess, caused by Streptococcus pneumoniae, other streptococci (excluding enterococci, e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, Haemophilus influenzae, and Bacteroides species.
(2) Urinary tract infections caused by Escherichia coli, Klebsiella species, Proteus mirabilis, Morganella morganii, Proteus vulgaris and Providencia species (including P. rettgeri).
(3) Intra-abdominal infections, including peritonitis and intra-abdominal abscess, caused by Escherichia coli, Klebsiella species, Bacteroides species including Bacteroides fragilis, and Clostridium species.
(4) Gynecological infections, including endometritis, pelvic cellulitis, and pelvic inflammatory disease caused by Escherichia coli, Neisseria gonorrhoeae (including penicillinase-producing strains), Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, Peptostreptococcus species and Streptococcus agalactiae. Cefoxitin for injection, like cephalosporins, has no activity against Chlamydia trachomatis. Therefore, when Cefoxitin for injection is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added.
(5) Septicemia caused by Streptococcus pneumoniae, Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, and Bacteroides species including B. fragilis.
(6) Bone and joint infections caused by Staphylococcus aureus (including penicillinase-producing strains).
(7) Skin and skin structure infections caused by Staphylococcus aureus (including penicillinase-producing strains), Staphylococcus epidermidis, Streptococcus pyogenes and other streptococci (excluding enterococci e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Escherichia coli, Proteus mirabilis, Klebsiella species, Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, and Peptostreptococcus species. Launch Date1.26826565E12 |
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Curative | Cefoxitin Approved UseCefoxitin for Injection, USP is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms in the diseases listed below.
(1) Lower respiratory tract infections, including pneumonia and lung abscess, caused by Streptococcus pneumoniae, other streptococci (excluding enterococci, e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, Haemophilus influenzae, and Bacteroides species.
(2) Urinary tract infections caused by Escherichia coli, Klebsiella species, Proteus mirabilis, Morganella morganii, Proteus vulgaris and Providencia species (including P. rettgeri).
(3) Intra-abdominal infections, including peritonitis and intra-abdominal abscess, caused by Escherichia coli, Klebsiella species, Bacteroides species including Bacteroides fragilis, and Clostridium species.
(4) Gynecological infections, including endometritis, pelvic cellulitis, and pelvic inflammatory disease caused by Escherichia coli, Neisseria gonorrhoeae (including penicillinase-producing strains), Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, Peptostreptococcus species and Streptococcus agalactiae. Cefoxitin for injection, like cephalosporins, has no activity against Chlamydia trachomatis. Therefore, when Cefoxitin for injection is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added.
(5) Septicemia caused by Streptococcus pneumoniae, Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, and Bacteroides species including B. fragilis.
(6) Bone and joint infections caused by Staphylococcus aureus (including penicillinase-producing strains).
(7) Skin and skin structure infections caused by Staphylococcus aureus (including penicillinase-producing strains), Staphylococcus epidermidis, Streptococcus pyogenes and other streptococci (excluding enterococci e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Escherichia coli, Proteus mirabilis, Klebsiella species, Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, and Peptostreptococcus species. Launch Date1.26826565E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFOXITIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFOXITIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFOXITIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFOXITIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 g single, intramuscular |
unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hoigne's syndrome... AEs leading to discontinuation/dose reduction: Hoigne's syndrome (1 patient) Sources: |
12 g 1 times / day multiple, intravenous Highest studied dose Dose: 12 g, 1 times / day Route: intravenous Route: multiple Dose: 12 g, 1 times / day Sources: |
unhealthy, 22 years n = 1 Health Status: unhealthy Condition: bacterial endocarditis Age Group: 22 years Sex: M Population Size: 1 Sources: |
|
2 g 3 times / day multiple, intravenous Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: |
unhealthy, 45 years n = 1 Health Status: unhealthy Age Group: 45 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hemolytic anemia... AEs leading to discontinuation/dose reduction: Hemolytic anemia (1 patient) Sources: |
1 g 4 times / day multiple, intravenous Dose: 1 g, 4 times / day Route: intravenous Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, 77 years n = 1 Health Status: unhealthy Condition: peritonitis Age Group: 77 years Sex: M Population Size: 1 Sources: |
Disc. AE: Hemolytic anemia, Pancytopenia... AEs leading to discontinuation/dose reduction: Hemolytic anemia (1 patient) Sources: Pancytopenia (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hoigne's syndrome | 1 patient Disc. AE |
2 g single, intramuscular |
unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: F Population Size: 1 Sources: |
Hemolytic anemia | 1 patient Disc. AE |
2 g 3 times / day multiple, intravenous Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: |
unhealthy, 45 years n = 1 Health Status: unhealthy Age Group: 45 years Sex: F Population Size: 1 Sources: |
Hemolytic anemia | 1 patient Disc. AE |
1 g 4 times / day multiple, intravenous Dose: 1 g, 4 times / day Route: intravenous Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, 77 years n = 1 Health Status: unhealthy Condition: peritonitis Age Group: 77 years Sex: M Population Size: 1 Sources: |
Pancytopenia | 1 patient Disc. AE |
1 g 4 times / day multiple, intravenous Dose: 1 g, 4 times / day Route: intravenous Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, 77 years n = 1 Health Status: unhealthy Condition: peritonitis Age Group: 77 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Ceftizoxime-induced hemolysis due to immune complexes: case report and determination of the epitope responsible for immune complex-mediated hemolysis. | 1999 Mar |
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[Occurrence of beta-lactamase type ESBL and IBL in Pseudomonas aeruginosa rods]. | 2001 |
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Antibacterial susceptibility of intestinal lactobacilli of healthy children. | 2001 |
|
Occurrence of metronidazole and imipenem resistance among Bacteroides fragilis group clinical isolates in Hungary. | 2001 |
|
Clinical features of patients with invasive Eikenella corrodens infections and microbiological characteristics of the causative isolates. | 2001 Apr |
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[Staphylococcus aureus: new detection of intrinsic resistance using the diffusion method]. | 2001 Apr |
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A novel metallo-beta-lactamase, Mbl1b, produced by the environmental bacterium Caulobacter crescentus. | 2001 Dec 14 |
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Nosocomial bloodstream infection in pediatric patients: Siriraj Hospital, Bangkok; 1996-1999. | 2001 Feb |
|
A randomised controlled trial of antibiotic prophylaxis in elective caesarean delivery. | 2001 Feb |
|
Plasmid-mediated and inducible cephalosporinase DHA-2 from Klebsiella pneumoniae. | 2001 Feb |
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Inactivation of Aeromonas hydrophila metallo-beta-lactamase by cephamycins and moxalactam. | 2001 Jul |
|
Detection of beta-lactamase-mediated resistance. | 2001 Jul |
|
Susceptibility of the Bacteroides fragilis group to newer quinolones and other standard anti-anaerobic agents. | 2001 Jul |
|
Antibiotic therapy in intra-abdominal infections--a review on randomised clinical trials. | 2001 Jul 30 |
|
Antibacterial effect of antibiotic solution on cellular viability in canine veins. | 2001 Jun |
|
Antimicrobial resistance surveillance of bacteria in 1999 in Korea with a special reference to resistance of enterococci to vancomycin and gram-negative bacilli to third generation cephalosporin, imipenem, and fluoroquinolone. | 2001 Jun |
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Antimicrobial resistance of Shigella sonnei in Korea during the last two decades. | 2001 Mar |
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Cephalosporins in surgical prophylaxis. | 2001 Nov |
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Molecular mechanisms of cefoxitin resistance in Escherichia coli from the Toronto area hospitals. | 2001 Sep-Oct |
|
Detection and typing of extended-spectrum beta-lactamases in clinical isolates of the family Enterobacteriaceae in a medical center in Turkey. | 2001 Summer |
|
Influence of failure of primary wound healing on subsequent recurrence of pilonidal sinus. combined prospective study and randomised controlled trial. | 2002 |
|
Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis. | 2002 |
|
Cross-reactivity of cefotetan and ceftriaxone antibodies, associated with hemolytic anemia, with other: cephalosporins and penicillin. | 2002 Aug |
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Increase in resistance to new fluoroquinolones from 1998 to 2001 in the Bacteroides fragilis group. | 2002 Dec |
|
Mycobacterium fortuitum complex endocarditis-case report and literature review. | 2002 Feb |
|
Crystal structures of the Bacillus licheniformis BS3 class A beta-lactamase and of the acyl-enzyme adduct formed with cefoxitin. | 2002 Feb 12 |
|
Surgical prophylaxis in practice. | 2002 Jan |
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Outbreak of multidrug-resistant Salmonella newport--United States, January-April 2002. | 2002 Jun 28 |
|
Escherichia coli isolated from seafood: toxicity and plasmid profiles. | 2002 Mar |
|
A pathway-specific cell based screening system to detect bacterial cell wall inhibitors. | 2002 Mar |
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The ACT-1 plasmid-encoded AmpC beta-lactamase is inducible: detection in a complex beta-lactamase background. | 2002 Mar |
|
[Genotypic exploration of a hospital neonatal outbreak due to Klebsiella pneumoniae producing extended-spectrum-betalactamase]. | 2002 May |
|
Cefepime MIC as a predictor of the extended-spectrum beta-lactamase type in Klebsiella pneumoniae, Taiwan. | 2002 May |
|
Rapidly growing members of the genus Mycobacterium affecting dogs and cats. | 2002 May-Jun |
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Comparison of screening methods for TEM- and SHV-derived extended-spectrum beta-lactamase detection. | 2002 Nov |
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Further modification of the Hodge test to screen AmpC beta-lactamase (CMY-1)-producing strains of Escherichia coli and Klebsiella pneumoniae. | 2002 Nov |
|
[Trends in antimicrobial utilization in a university hospital, 1990-1996]. | 2002 Oct |
|
Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains. | 2002 Oct |
|
[Activity of 14 antimicrobials against Eikenella corrodens]. | 2002 Oct-Dec |
|
Natural antibiotic susceptibility of Enterobacter amnigenus, Enterobacter cancerogenus, Enterobacter gergoviae and Enterobacter sakazakii strains. | 2002 Sep |
|
Selection of cefoxitin-resistant bacteroides thetaiotaomicron mutants and mechanisms involved in beta-lactam resistance. | 2002 Sep 1 |
|
Automated ribotyping and pulsed-field gel electrophoresis for rapid identification of multidrug-resistant Salmonella serotype newport. | 2003 Apr |
|
Endometritis does not predict reproductive morbidity after pelvic inflammatory disease. | 2003 Jan |
|
Efficacy and safety of azithromycin as monotherapy or combined with metronidazole compared with two standard multidrug regimens for the treatment of acute pelvic inflammatory disease. | 2003 Jan-Feb |
|
Isolation of Escherichia coli O157:H7 from intact colon fecal samples of swine. | 2003 Mar |
|
Emergence of ceftriaxone-resistant Salmonella isolates and rapid spread of plasmid-encoded CMY-2-like cephalosporinase, Taiwan. | 2003 Mar |
|
Changes in sensitivity patterns to selected antibiotics in Clostridium difficile in geriatric in-patients over an 18-month period. | 2003 Mar |
|
A seven-year survey of Klebsiella pneumoniae producing TEM-24 extended-spectrum beta-lactamase in Nice University Hospital (1994-2000). | 2003 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/cefoxitin.html
Adults
The usual adult dosage range is 1 gram to 2 grams every six to eight hours.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26629031
CEFOXITIN inhibited Mycobacterium fortuitum growth with MIC 32 ug/ml
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:33:47 UTC 2023
by
admin
on
Thu Jul 06 22:33:47 UTC 2023
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Record UNII |
6OEV9DX57Y
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000011161
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N0000011161
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N0000011161
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N0000011161
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NBK548666
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N0000011161
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N0000011161
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WHO-VATC |
QJ01DC01
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N0000011161
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N0000175488
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N0000011161
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N0000011161
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NCI_THESAURUS |
C357
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NDF-RT |
N0000011161
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NBK547862
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N0000011161
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N0000011161
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WHO-ATC |
J01DC01
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CHEMBL996
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M3208
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550
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252-641-2
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6OEV9DX57Y
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CEFOXITIN
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Cefoxitin
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3397
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SUB07409MIG
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209807
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D002440
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2189
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100000081807
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DB01331
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C61665
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441199
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SALT/SOLVATE -> PARENT |
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|
BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
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