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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H12Cl2N2O5.C4H6O4.C2H7NO
Molecular Weight 502.301
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORAMPHENICOL MONOETHANOLAMINE SUCCINATE

SMILES

NCCO.OC(=O)CCC(O)=O.OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O

InChI

InChIKey=GLOVPJIOQKHINH-UONRGADFSA-N
InChI=1S/C11H12Cl2N2O5.C4H6O4.C2H7NO/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20;5-3(6)1-2-4(7)8;3-1-2-4/h1-4,8-10,16-17H,5H2,(H,14,18);1-2H2,(H,5,6)(H,7,8);4H,1-3H2/t8-,9-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C2H7NO
Molecular Weight 61.0831
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C11H12Cl2N2O5
Molecular Weight 323.129
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity ( - )

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CHLOROPTIC
PubMed

PubMed

TitleDatePubMed
Survey of yeast mastitis in dairy herds of small-type farms in the Lublin region, Poland.
2001
Carbon and nitrogen removal from a wastewater of an industrial dairy laboratory with a coupled anaerobic filter-sequencing batch reactor system.
2001
Numerical methods for handling uncertainty in microarray data: an example analyzing perturbed mitochondrial function in yeast.
2001
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA.
2001
Amplification of the Escherichia coli lacZ gene in Bacillus subtilis and its expression on a by-product growth medium.
2001
Disposition kinetics of florfenicol in goats by using two analytical methods.
2001 Apr
Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait.
2001 Apr
Antimicrobial resistance of Streptococcus pneumoniae at a university hospital in Saudi Arabia.
2001 Apr
Strain differences in haematological response to chloramphenicol succinate in mice: implications for toxicological research.
2001 Apr
Randomised controlled trial of ketorolac in the management of corneal abrasions.
2001 Apr
Plasmid transfer and susceptibility to antibiotics in the halophilic phototrophs Rhodovibrio salinarum and Rhodothalassium salexigens.
2001 Apr 1
UV-induced increase in RNA polymerase activity in Xanthomonas oryzae pathovar oryzae.
2001 Aug
Liposome-mediated DNA uptake and transient expression in Thermotoga.
2001 Feb
Molecular epidemiology of multiple drug resistant type 6B Streptococcus pneumoniae in the Northern Territory and Queensland, Australia.
2001 Feb
A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli.
2001 Jan
Chloramphenicol treatment for vancomycin-resistant Enterococcus faecium bacteremia.
2001 Jan
Interaction of human aldehyde dehydrogenase with aromatic substrates and ligands.
2001 Jan 30
Drug resistant Haemophilus influenzae from respiratory tract infection in a tertiary care hospital in north India.
2001 Jan-Mar
Antibacterial activity of 4,5-dihydroxy-2-cyclopentan-1-one (DHCP) and cloning of a gene conferring DHCP resistance in Escherichia coli.
2001 Jul
A novel heat shock protein plays an important role in thermal stress management in cyanobacteria.
2001 Jul 6
Cloning and functional analysis of a phosphopantetheinyl transferase superfamily gene associated with jadomycin biosynthesis in Streptomyces venezuelae ISP5230.
2001 Jun
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
External quality assessment of antimicrobial susceptibility testing in Europe.
2001 Jun
Screening of antibiotic resistant inhibitors from local plant materials against two different strains of Pseudomonas aeruginosa.
2001 Jun
Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal.
2001 Jun 1
[Susceptibility of non-typhi Salmonella spp. at the Galdakao Hospital (1992-1998)].
2001 Mar
Analysis of a conserved hydrophobic pocket important for the thermostability of Bacillus pumilus chloramphenicol acetyltransferase (CAT-86).
2001 Mar
Occurrence of the vanA and vanC2/C3 genes in Enterococcus species isolated from poultry sources in Malaysia.
2001 Mar
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001 Mar
Antimicrobial susceptibility of Listeria monocytogenes isolated from meningoencephalitis in sheep.
2001 Mar
Antimicrobial resistance of Enterococci in Lebanon.
2001 Mar
Clostridium sordelii corneal ulcer.
2001 Mar-Apr
Induction of complement sensitivity in Escherichia coli by citric acid and low pH.
2001 May
Natural antibiotic susceptibility of Klebsiella pneumoniae, K. oxytoca, K. planticola, K. ornithinolytica and K. terrigena strains.
2001 May
In vitro susceptibility of Vibrio spp. isolated from the environment.
2001 May
High prevalence of carriage of antibiotic-resistant Streptococcus pneumoniae in children in Kampala Uganda.
2001 May
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.
2001 May
Carriage of antibiotic-resistant bacteria by healthy children.
2001 May
Comparative study of the influence of melatonin and vitamin E on the surface characteristics of Escherichia coli.
2001 May
Neisseria meningitidis with decreased susceptibility to penicillin in Ontario, Canada 1997-2000.
2001 May 1
Successful treatment of vancomycin-resistant Enterococcus endocarditis with oral linezolid.
2001 May 1
Increased mitochondrial-encoded gene transcription in immortal DF-1 cells.
2001 May 1
Clinical prevalence, antimicrobial susceptibility, and geographic resistance patterns of enterococci: results from the SENTRY Antimicrobial Surveillance Program, 1997-1999.
2001 May 15
Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999.
2001 May 15
Decreased susceptibility to ciprofloxacin in Salmonella enterica serotype typhi, United Kingdom.
2001 May-Jun
Methicillin-resistant staphylococci and ofloxacin-resistant bacteria from clinically healthy conjunctivas.
2001 May-Jun
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
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center.
2001 Spring
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 Vivo Use Guide
Chloramphenicol 0.5% Eye Drops
Route of Administration: Topical
In Vitro Use Guide
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).
Substance Class Chemical
Created
by admin
on Tue Oct 22 12:35:32 UTC 2019
Edited
by admin
on Tue Oct 22 12:35:32 UTC 2019
Record UNII
FMO6OC31WV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORAMPHENICOL MONOETHANOLAMINE SUCCINATE
Common Name English
BUTANEDIOIC ACID, COMPD. WITH 2-AMINOETHANOL AND 2,2-DICHLORO-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL)ACETAMIDE (1:1:1)
Systematic Name English
SUCCINIC ACID, COMPD. WITH 2-AMINOETHANOL AND 2,2-DICHLORO-N-(.BETA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-P-NITROPHENETHYL)ACETAMIDE (1:1:1), D-THREO-(-)-
Systematic Name English
Code System Code Type Description
CAS
20369-85-1
Created by admin on Tue Oct 22 12:35:32 UTC 2019 , Edited by admin on Tue Oct 22 12:35:32 UTC 2019
PRIMARY
Related Record Type Details
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