Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H16Cl2N2O8 |
Molecular Weight | 423.202 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]([C@@H](COC(=O)CCC(O)=O)NC(=O)C(Cl)Cl)C1=CC=C(C=C1)[N+]([O-])=O
InChI
InChIKey=LIRCDOVJWUGTMW-ZWNOBZJWSA-N
InChI=1S/C15H16Cl2N2O8/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21)/t10-,13-/m1/s1
Chloramphenicol is a broad-spectrum antibiotic that was first isolated from
Streptomyces venezuelae in 1947. The drug was subsequently chemically synthesized. It has both a bacteriostatic and bactericidal effect; in the usual therapeutic concentrations it is bacteriostatic. Chloramphenicol is used for the treatment of serious gram-negative, gram-positive, and anaerobic infections. It is especially useful in the treatment of meningitis, typhoid fever, and cystic fibrosis. It should be reserved for infections for which other drugs are ineffective or contraindicated. Chloramphenicol, a small inhibitor of bacterial protein synthesis, is active against a variety of bacteria and readily enters the CSF. It has been used extensively in the last decades for the treatment of bacterial meningitis. In industrialized countries, chloramphenicol is restricted mostly to topical uses because of the risk of induction of aplastic anemia. However, it remains a valuable reserve antibiotic for patients with allergy to β-lactam antibiotics or with CNS infections caused by multiresistant pathogens.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: intestinal esterase Sources: https://www.iasj.net/iasj?func=article&aId=41875 |
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Target ID: CHEMBL2363135 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | CHLOROPTIC Approved UseIndications and Usage In accord with the concepts in the Warning Box and this section, chloramphenicolmust be used only in those serious infections for which less potentially dangerous drugs are ineffective or contraindicated. However, chloramphenicol may be chosen to initiate antibiotic therapy on the clinical impression that one of the conditions below is believed to be present; in vitro sensitivity tests should be performed concurrently so that the drug may be discontinued as soon as possible if less potentially dangerous agents are indicated by such tests. The decision to continue use of chloramphenicol rather than another antibiotic when both are suggested by in vitro studies to be effective against a specific pathogen should be based upon severity of the infection, susceptibility of the pathogen to the various antimicrobial drugs, efficacy of the various drugs in the infection, and the important additional concepts contained in the Warning Box above. 1. Acute infections caused by Salmonella typhi* It is not recommended for the routine treatment of the typhoid carrier state. 2. Serious infections caused by susceptible strains in accordance with the concepts expressed above: a) Salmonella species b) H. influenzae, specially meningeal infections c) Rickettsia d) Lymphogranuloma-psittacosis group e) Various gram-negative bacteria causing bacteremia, meningitis, or other serious gram-negative infections f) Other susceptible organisms which have been demonstrated to be resistant to all other appropriate antimicrobial agents. 3. Cystic fibrosis regimens *In treatment of typhoid fever some authorities recommend that chloramphenicol be administered at therapeutic levels for 8 to 10 days after the patient has become afebrile to lessen the possibility of relapse. Launch Date1968 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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16.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2713219/ |
500 mg 4 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
59.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2713219/ |
500 mg 4 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2713219/ |
500 mg 4 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7463235/ |
25 mg/kg 4 times / day multiple, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL serum | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7463235/ |
25 mg/kg 4 times / day multiple, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL SUCCINATE serum | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.5 % 4 times / day multiple, ophthalmic Recommended Dose: 0.5 %, 4 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 4 times / day Sources: |
unhealthy, 0.5 - 12 years n = 163 Health Status: unhealthy Condition: acute infective conjunctivitis Age Group: 0.5 - 12 years Sex: unknown Population Size: 163 Sources: |
Other AEs: Swollen eyelid... |
0.25 g 1 times / 3 months multiple, intramuscular Recommended Dose: 0.25 g, 1 times / 3 months Route: intramuscular Route: multiple Dose: 0.25 g, 1 times / 3 months Sources: |
unhealthy, 11 years n = 1 Health Status: unhealthy Condition: infection Age Group: 11 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
70 mg/kg 1 times / day steady, intravenous Recommended Dose: 70 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 70 mg/kg, 1 times / day Co-administed with:: (meropenem) Sources: 120 mg/kg/day |
unhealthy, 15 years n = 1 Health Status: unhealthy Condition: Cystic Fibrosis and infection Age Group: 15 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hyperlactatemia... AEs leading to discontinuation/dose reduction: Hyperlactatemia (1 patient) Sources: |
3 g 1 times / day multiple, intravenous Recommended Dose: 3 g, 1 times / day Route: intravenous Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 23 years n = 1 Health Status: unhealthy Condition: infection Age Group: 23 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
2.5 g 1 times / day multiple, intravenous Recommended Dose: 2.5 g, 1 times / day Route: intravenous Route: multiple Dose: 2.5 g, 1 times / day Sources: |
unhealthy, 27 years n = 1 Health Status: unhealthy Condition: infection Age Group: 27 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
1 g 1 times / day multiple, parenteral Recommended Dose: 1 g, 1 times / day Route: parenteral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: infection Age Group: 39 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
750 mg 4 times / day steady, intravenous Recommended Dose: 750 mg, 4 times / day Route: intravenous Route: steady Dose: 750 mg, 4 times / day Co-administed with:: tobramycin Sources: nafcillin |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: purulent drainage from the surgical wound Age Group: 54 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
4 g 1 times / day multiple, intravenous Recommended Dose: 4 g, 1 times / day Route: intravenous Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy, 61 years n = 1 Health Status: unhealthy Condition: infection Age Group: 61 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
1 g 1 times / day multiple, intramuscular Recommended Dose: 1 g, 1 times / day Route: intramuscular Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 68 years n = 1 Health Status: unhealthy Condition: infection Age Group: 68 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
2 g 1 times / day multiple, parenteral Recommended Dose: 2 g, 1 times / day Route: parenteral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 71 years n = 1 Health Status: unhealthy Condition: infection Age Group: 71 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
3 % 1 times / day multiple, topical Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: |
unhealthy, adult n = 23 Health Status: unhealthy Condition: cancer patients with (EGFRI)-induced papulopustular rash Age Group: adult Sex: unknown Population Size: 23 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Swollen eyelid | 1 patient | 0.5 % 4 times / day multiple, ophthalmic Recommended Dose: 0.5 %, 4 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 4 times / day Sources: |
unhealthy, 0.5 - 12 years n = 163 Health Status: unhealthy Condition: acute infective conjunctivitis Age Group: 0.5 - 12 years Sex: unknown Population Size: 163 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
0.25 g 1 times / 3 months multiple, intramuscular Recommended Dose: 0.25 g, 1 times / 3 months Route: intramuscular Route: multiple Dose: 0.25 g, 1 times / 3 months Sources: |
unhealthy, 11 years n = 1 Health Status: unhealthy Condition: infection Age Group: 11 years Sex: F Population Size: 1 Sources: |
Hyperlactatemia | 1 patient Disc. AE |
70 mg/kg 1 times / day steady, intravenous Recommended Dose: 70 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 70 mg/kg, 1 times / day Co-administed with:: (meropenem) Sources: 120 mg/kg/day |
unhealthy, 15 years n = 1 Health Status: unhealthy Condition: Cystic Fibrosis and infection Age Group: 15 years Sex: F Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
3 g 1 times / day multiple, intravenous Recommended Dose: 3 g, 1 times / day Route: intravenous Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 23 years n = 1 Health Status: unhealthy Condition: infection Age Group: 23 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
2.5 g 1 times / day multiple, intravenous Recommended Dose: 2.5 g, 1 times / day Route: intravenous Route: multiple Dose: 2.5 g, 1 times / day Sources: |
unhealthy, 27 years n = 1 Health Status: unhealthy Condition: infection Age Group: 27 years Sex: F Population Size: 1 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
1 g 1 times / day multiple, parenteral Recommended Dose: 1 g, 1 times / day Route: parenteral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: infection Age Group: 39 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
750 mg 4 times / day steady, intravenous Recommended Dose: 750 mg, 4 times / day Route: intravenous Route: steady Dose: 750 mg, 4 times / day Co-administed with:: tobramycin Sources: nafcillin |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: purulent drainage from the surgical wound Age Group: 54 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
4 g 1 times / day multiple, intravenous Recommended Dose: 4 g, 1 times / day Route: intravenous Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy, 61 years n = 1 Health Status: unhealthy Condition: infection Age Group: 61 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
1 g 1 times / day multiple, intramuscular Recommended Dose: 1 g, 1 times / day Route: intramuscular Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 68 years n = 1 Health Status: unhealthy Condition: infection Age Group: 68 years Sex: F Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
2 g 1 times / day multiple, parenteral Recommended Dose: 2 g, 1 times / day Route: parenteral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 71 years n = 1 Health Status: unhealthy Condition: infection Age Group: 71 years Sex: F Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 375.9 uM] | ||||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
yes [IC50 32 uM] | |||
yes [IC50 48.1 uM] |
PubMed
Title | Date | PubMed |
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Survey of yeast mastitis in dairy herds of small-type farms in the Lublin region, Poland. | 2001 |
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Carbon and nitrogen removal from a wastewater of an industrial dairy laboratory with a coupled anaerobic filter-sequencing batch reactor system. | 2001 |
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Numerical methods for handling uncertainty in microarray data: an example analyzing perturbed mitochondrial function in yeast. | 2001 |
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A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA. | 2001 |
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Amplification of the Escherichia coli lacZ gene in Bacillus subtilis and its expression on a by-product growth medium. | 2001 |
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Disposition kinetics of florfenicol in goats by using two analytical methods. | 2001 Apr |
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Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait. | 2001 Apr |
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Antimicrobial resistance of Streptococcus pneumoniae at a university hospital in Saudi Arabia. | 2001 Apr |
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Strain differences in haematological response to chloramphenicol succinate in mice: implications for toxicological research. | 2001 Apr |
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Randomised controlled trial of ketorolac in the management of corneal abrasions. | 2001 Apr |
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Plasmid transfer and susceptibility to antibiotics in the halophilic phototrophs Rhodovibrio salinarum and Rhodothalassium salexigens. | 2001 Apr 1 |
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UV-induced increase in RNA polymerase activity in Xanthomonas oryzae pathovar oryzae. | 2001 Aug |
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Liposome-mediated DNA uptake and transient expression in Thermotoga. | 2001 Feb |
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Molecular epidemiology of multiple drug resistant type 6B Streptococcus pneumoniae in the Northern Territory and Queensland, Australia. | 2001 Feb |
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A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli. | 2001 Jan |
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Chloramphenicol treatment for vancomycin-resistant Enterococcus faecium bacteremia. | 2001 Jan |
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Interaction of human aldehyde dehydrogenase with aromatic substrates and ligands. | 2001 Jan 30 |
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Drug resistant Haemophilus influenzae from respiratory tract infection in a tertiary care hospital in north India. | 2001 Jan-Mar |
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Antibacterial activity of 4,5-dihydroxy-2-cyclopentan-1-one (DHCP) and cloning of a gene conferring DHCP resistance in Escherichia coli. | 2001 Jul |
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A novel heat shock protein plays an important role in thermal stress management in cyanobacteria. | 2001 Jul 6 |
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Cloning and functional analysis of a phosphopantetheinyl transferase superfamily gene associated with jadomycin biosynthesis in Streptomyces venezuelae ISP5230. | 2001 Jun |
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Distribution of resistance genes tet(M), aph3'-III, catpC194 and the integrase gene of Tn1545 in clinical Streptococcus pneumoniae harbouring erm(B) and mef(A) genes in Spain. | 2001 Jun |
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External quality assessment of antimicrobial susceptibility testing in Europe. | 2001 Jun |
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Screening of antibiotic resistant inhibitors from local plant materials against two different strains of Pseudomonas aeruginosa. | 2001 Jun |
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Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal. | 2001 Jun 1 |
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[Susceptibility of non-typhi Salmonella spp. at the Galdakao Hospital (1992-1998)]. | 2001 Mar |
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Analysis of a conserved hydrophobic pocket important for the thermostability of Bacillus pumilus chloramphenicol acetyltransferase (CAT-86). | 2001 Mar |
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Occurrence of the vanA and vanC2/C3 genes in Enterococcus species isolated from poultry sources in Malaysia. | 2001 Mar |
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Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998. | 2001 Mar |
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Antimicrobial susceptibility of Listeria monocytogenes isolated from meningoencephalitis in sheep. | 2001 Mar |
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Antimicrobial resistance of Enterococci in Lebanon. | 2001 Mar |
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Clostridium sordelii corneal ulcer. | 2001 Mar-Apr |
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Induction of complement sensitivity in Escherichia coli by citric acid and low pH. | 2001 May |
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Natural antibiotic susceptibility of Klebsiella pneumoniae, K. oxytoca, K. planticola, K. ornithinolytica and K. terrigena strains. | 2001 May |
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In vitro susceptibility of Vibrio spp. isolated from the environment. | 2001 May |
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High prevalence of carriage of antibiotic-resistant Streptococcus pneumoniae in children in Kampala Uganda. | 2001 May |
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In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico. | 2001 May |
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Carriage of antibiotic-resistant bacteria by healthy children. | 2001 May |
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Comparative study of the influence of melatonin and vitamin E on the surface characteristics of Escherichia coli. | 2001 May |
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Neisseria meningitidis with decreased susceptibility to penicillin in Ontario, Canada 1997-2000. | 2001 May 1 |
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Successful treatment of vancomycin-resistant Enterococcus endocarditis with oral linezolid. | 2001 May 1 |
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Increased mitochondrial-encoded gene transcription in immortal DF-1 cells. | 2001 May 1 |
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Clinical prevalence, antimicrobial susceptibility, and geographic resistance patterns of enterococci: results from the SENTRY Antimicrobial Surveillance Program, 1997-1999. | 2001 May 15 |
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Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999. | 2001 May 15 |
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Decreased susceptibility to ciprofloxacin in Salmonella enterica serotype typhi, United Kingdom. | 2001 May-Jun |
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Methicillin-resistant staphylococci and ofloxacin-resistant bacteria from clinically healthy conjunctivas. | 2001 May-Jun |
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Prevalence of serotypes and molecular epidemiology of Streptococcus pneumoniae strains isolated from children in Beijing, China: identification of two novel multiply-resistant clones. | 2001 Spring |
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Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center. | 2001 Spring |
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In vitro activity of 19 antimicrobial agents against enterococci from healthy subjects and hospitalized patients and use of an ace gene probe from Enterococcus faecalis for species identification. | 2001 Spring |
|
Variation in clonality and antibiotic-resistance genes among multiresistant Salmonella enterica serotype typhimurium phage-type U302 (MR U302) from humans, animals, and foods. | 2001 Spring |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15227603
The highest activity of chloramphenicol was documented for isolates of Stenotrophomonas maltophilia (76,5 % susceptible, MIC50 = 4 mg/L, MIC90 = 16 mg/L) and of Staphylococcus aureus (76,2 % susceptible, MIC50 = 8 mg/L, MIC90 = 16 mg/L).
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3544-94-3
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SUB01205MIG
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4653
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20769
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DTXSID8048155
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Chloramphenicol succinate
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756676
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656580
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DB07565
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100000084708
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ZCX619U9A1
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222-590-0
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ACTIVE MOIETY
SUBSTANCE RECORD