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
CO[C@]2(NC(=O)CC1=CC=CS1)[C@H]3SCC(COC(N)=O)=C(N3C2=O)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 Date2010 |
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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 Date2010 |
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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 Date2010 |
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 |
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 |
|
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 |
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 |
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 |
| 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 |
| 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 |
| 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Multiple antibiotic-resistance mechanisms including a novel combination of extended-spectrum beta-lactamases in a Klebsiella pneumoniae clinical strain isolated in Argentina. | 2003-07 |
|
| Sequence analysis and biochemical characterisation of chromosomal CAV-1 (Aeromonas caviae), the parental cephalosporinase of plasmid-mediated AmpC 'FOX' cluster. | 2003-05-16 |
|
| A seven-year survey of Klebsiella pneumoniae producing TEM-24 extended-spectrum beta-lactamase in Nice University Hospital (1994-2000). | 2003-05 |
|
| Automated ribotyping and pulsed-field gel electrophoresis for rapid identification of multidrug-resistant Salmonella serotype newport. | 2003-04 |
|
| Natural antimicrobial susceptibilities of strains of 'unusual' Serratia species: S. ficaria, S. fonticola, S. odorifera, S. plymuthica and S. rubidaea. | 2003-04 |
|
| 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. | 2003-03-15 |
|
| Group 1 beta-lactamases of Aeromonas caviae and their resistance to beta-lactam antibiotics. | 2003-03 |
|
| Isolation of Escherichia coli O157:H7 from intact colon fecal samples of swine. | 2003-03 |
|
| Emergence of ceftriaxone-resistant Salmonella isolates and rapid spread of plasmid-encoded CMY-2-like cephalosporinase, Taiwan. | 2003-03 |
|
| Changes in sensitivity patterns to selected antibiotics in Clostridium difficile in geriatric in-patients over an 18-month period. | 2003-03 |
|
| Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates. | 2003-03 |
|
| [Activity of 14 antimicrobials against Eikenella corrodens]. | 2003-02-26 |
|
| Pelvic inflammatory disease: how should it be managed? | 2003-02 |
|
| Occurrence and detection of AmpC beta-lactamases among Gram-negative clinical isolates using a modified three-dimensional test at Guru Tegh Bahadur Hospital, Delhi, India. | 2003-02 |
|
| Endometritis does not predict reproductive morbidity after pelvic inflammatory disease. | 2003-01 |
|
| Antibiotic resistance of Neisseria gonorrhoeae in Spain: trends over the last two decades. | 2003-01 |
|
| Beta-lactamase characterization in Escherichia coli isolates with diminished susceptibility or resistance to extended-spectrum cephalosporins recovered from sick animals in Spain. | 2003 |
|
| High-dose antibiotic therapy is superior to a 3-drug combination of prostanoids and lipid A derivative in protecting irradiated canines. | 2002-12 |
|
| Increase in resistance to new fluoroquinolones from 1998 to 2001 in the Bacteroides fragilis group. | 2002-12 |
|
| Antibacterial activity of moxifloxacin against periodontal anaerobic pathogens involved in systemic infections. | 2002-12 |
|
| beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 2002-11 |
|
| Comparison of screening methods for TEM- and SHV-derived extended-spectrum beta-lactamase detection. | 2002-11 |
|
| Comparative in vitro activities of ertapenem against bacterial pathogens from patients with acute pelvic infection. | 2002-11 |
|
| Further modification of the Hodge test to screen AmpC beta-lactamase (CMY-1)-producing strains of Escherichia coli and Klebsiella pneumoniae. | 2002-11 |
|
| Molecular epidemiology of a citywide outbreak of extended-spectrum beta-lactamase-producing Klebsiella pneumoniae infection. | 2002-10-01 |
|
| Epidemiological and antibiotic resistant study on extended-spectrum beta-lactamase-producing Escherichia coli and Klebsiella pneumoniae in Zhejiang Province. | 2002-10 |
|
| [Trends in antimicrobial utilization in a university hospital, 1990-1996]. | 2002-10 |
|
| Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains. | 2002-10 |
|
| Nontuberculous mycobacterial pulmonary diseases in immunocompetent patients. | 2002-09-25 |
|
| Selection of cefoxitin-resistant bacteroides thetaiotaomicron mutants and mechanisms involved in beta-lactam resistance. | 2002-09-01 |
|
| Multilaboratory comparison of anaerobe susceptibility results using 3 different agar media. | 2002-09-01 |
|
| Natural antibiotic susceptibility of Enterobacter amnigenus, Enterobacter cancerogenus, Enterobacter gergoviae and Enterobacter sakazakii strains. | 2002-09 |
|
| Klebsiella and enterobacter: antibiotic resistance and treatment implications. | 2002-09 |
|
| Susceptibility to antibiotics and biochemical properties of Desulfovibrio desulfuricans strains. | 2002-08-29 |
|
| Klebsiella pneumoniae: epidemiology and analysis of risk factors for infections caused by resistant strains. | 2002-08 |
|
| Cross-reactivity of cefotetan and ceftriaxone antibodies, associated with hemolytic anemia, with other: cephalosporins and penicillin. | 2002-08 |
|
| Comparison of several methods used for the determination of cephalosporins. Analysis of cephalexin in pharmaceutical samples. | 2002-07-01 |
|
| Occurrence and characterization of resistance to extended-spectrum cephalosporins mediated by beta-lactamase CMY-2 in Salmonella isolated from food-producing animals in Canada. | 2002-07 |
|
| Outbreak of multidrug-resistant Salmonella newport--United States, January-April 2002. | 2002-06-28 |
|
| Outpatient pelvic inflammatory disease treatment as effective as inpatient care, study finds. | 2002-06-14 |
|
| Clinical review: bacteremia caused by anaerobic bacteria in children. | 2002-06 |
|
| Characterization of cefotaxime-resistant Escherichia coli isolates from a nosocomial outbreak at three geriatric hospitals. | 2002-06 |
|
| [Genotypic exploration of a hospital neonatal outbreak due to Klebsiella pneumoniae producing extended-spectrum-betalactamase]. | 2002-05 |
|
| Proposed protocol to reduce bacterial infectious complications in living related small bowel transplant recipients. | 2002-05 |
|
| Antibiotic sensitivities of common bacterial pathogens in urinary tract infections at Gondar Hospital, Ethiopia. | 2002-03 |
|
| Escherichia coli isolated from seafood: toxicity and plasmid profiles. | 2002-03 |
|
| [Extended-spectrum beta-lactamase detection in Enterobacteriaceae and antibiotic susceptibility analysis]. | 2002-02-28 |
|
| [Multidrug resistance in Klebsiella pneumoniae: multicenter study]. | 2002-01 |
|
| Influence of failure of primary wound healing on subsequent recurrence of pilonidal sinus. combined prospective study and randomised controlled trial. | 2002 |
|
| A clinical strain of Escherichia coli possessing CMY-2 plasmid-mediated amp C beta-lactamase: an emerging concern in pediatrics? | 2002 |
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
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| Record UNII |
6OEV9DX57Y
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Validated (UNII)
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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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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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C357
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N0000011161
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NBK547862
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N0000011161
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J01DC01
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441199
Created by
admin on Wed Apr 02 08:45:38 GMT 2025 , Edited by admin on Wed Apr 02 08:45:38 GMT 2025
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PRIMARY |
| Related Record | Type | Details | ||
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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 |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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