Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H17N3O7S2 |
Molecular Weight | 427.4549 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@]1(C(=O)N2C(=C(COC(=N)O)CS[C@]12[H])C(=O)O)N=C(Cc3cccs3)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 | 427.4549 |
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 |
---|---|---|
Occurrence and transferability of beta-lactam resistance in Enterobacteriaceae isolated in Children's University Hospital in Bratislava. | 2001 |
|
[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 |
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Improved methods for detection of methicillin-resistant Staphylococcus aureus. | 2001 Apr |
|
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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Mechanism of reaction of acyl phosph(on)ates with the beta-lactamase of Enterobacter cloacae P99. | 2001 Apr 17 |
|
Prevalence and analysis of risk factors for infections caused by resistant Escherichia coli strains in Anhui, China. | 2001 Aug |
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Antimicrobial resistance of strains of the Bacteroides fragilis group isolated from the intestinal tract of children and adults in Brazil. | 2001 Aug |
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Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex. | 2001 Dec |
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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 |
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A randomised controlled trial of antibiotic prophylaxis in elective caesarean delivery. | 2001 Feb |
|
Anti-anaerobic activity of antibacterial agents. | 2001 Feb |
|
Possible asymptomatic carrier of salmonella typhimurium in the preputium: a case report. | 2001 Jan-Mar |
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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 |
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Laparoscopic management of gallstone ileus. | 2001 Jul-Sep |
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Antibacterial effect of antibiotic solution on cellular viability in canine veins. | 2001 Jun |
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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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Interaction energies between beta-lactam antibiotics and E. coli penicillin-binding protein 5 by reversible thermal denaturation. | 2001 Jun |
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Influence of in-vivo endotoxin liberation on anti-anaerobic antimicrobial efficacy. | 2001 Oct |
|
[A study on beta-lactamase activity of biofilm Escherichia coli]. | 2001 Sep |
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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 |
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Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis. | 2002 |
|
A luminescent Escherichia coli biosensor for the high throughput detection of beta-lactams. | 2002 Apr |
|
Klebsiella pneumoniae: epidemiology and analysis of risk factors for infections caused by resistant strains. | 2002 Aug |
|
[Identification of plasmid-encoded cephalosporinase ACC-1 among various enterobacteria (Klebsiella pneumoniae, Proteus mirabilis, Salmonella) isolated from a Tunisian hospital (Sfax 997-2000)]. | 2002 Feb |
|
Multicentre evaluation of the VITEK 2 Advanced Expert System for interpretive reading of antimicrobial resistance tests. | 2002 Feb |
|
Characterization of blaCMY-11, an AmpC-type plasmid-mediated beta-lactamase gene in a Korean clinical isolate of Escherichia coli. | 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 |
|
[Multidrug resistance in Klebsiella pneumoniae: multicenter study]. | 2002 Jan |
|
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'. | 2002 Jan |
|
Primary liver abscess caused by one clone of Klebsiella pneumoniae with two colonial morphotypes and resistotypes. | 2002 Jan |
|
Comparison of several methods used for the determination of cephalosporins. Analysis of cephalexin in pharmaceutical samples. | 2002 Jul 1 |
|
Nontuberculous mycobacterial pulmonary diseases in immunocompetent patients. | 2002 Jul-Sep |
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Escherichia coli isolated from seafood: toxicity and plasmid profiles. | 2002 Mar |
|
The ACT-1 plasmid-encoded AmpC beta-lactamase is inducible: detection in a complex beta-lactamase background. | 2002 Mar |
|
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 |
|
Klebsiella and enterobacter: antibiotic resistance and treatment implications. | 2002 Sep |
|
Automated ribotyping and pulsed-field gel electrophoresis for rapid identification of multidrug-resistant Salmonella serotype newport. | 2003 Apr |
|
Natural antimicrobial susceptibilities of strains of 'unusual' Serratia species: S. ficaria, S. fonticola, S. odorifera, S. plymuthica and S. rubidaea. | 2003 Apr |
|
Group 1 beta-lactamases of Aeromonas caviae and their resistance to beta-lactam antibiotics. | 2003 Mar |
|
Isolation of Escherichia coli O157:H7 from intact colon fecal samples of swine. | 2003 Mar |
|
Changes in sensitivity patterns to selected antibiotics in Clostridium difficile in geriatric in-patients over an 18-month period. | 2003 Mar |
|
Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates. | 2003 Mar |
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
Sat Jun 26 00:24:18 UTC 2021
by
admin
on
Sat Jun 26 00:24:18 UTC 2021
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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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LIVERTOX |
167
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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WHO-VATC |
QJ01DC01
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NDF-RT |
N0000011161
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NDF-RT |
N0000175488
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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NCI_THESAURUS |
C357
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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WHO-ATC |
J01DC01
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CHEMBL996
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M3208
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PRIMARY | Merck Index | ||
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550
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252-641-2
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35607-66-0
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CEFOXITIN
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Cefoxitin
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1098107
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PRIMARY | USP-RS | ||
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3397
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SUB07409MIG
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D002440
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2189
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6OEV9DX57Y
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DB01331
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C61665
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35607-66-0
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441199
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Biological Half-life | PHARMACOKINETIC |
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