U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H12Cl2N2O5
Molecular Weight 323.129
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORAMPHENICOL

SMILES

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

InChI

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

HIDE SMILES / InChI

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

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
The adverse neuro-developmental effects of postnatal steroids in the preterm infant: a systematic review of RCTs.
2001
Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait.
2001 Apr
Strain differences in haematological response to chloramphenicol succinate in mice: implications for toxicological research.
2001 Apr
Toxicity of natural tear substitutes in a fully defined culture model of human corneal epithelial cells.
2001 Apr
Sex-related differences in antinociception and tolerance development following chronic intravenous infusion of morphine in the rat: modulatory role of testosterone via morphine clearance.
2001 Apr
Plasmid transfer and susceptibility to antibiotics in the halophilic phototrophs Rhodovibrio salinarum and Rhodothalassium salexigens.
2001 Apr 1
Streptococcus pneumoniae nasopharyngeal carriage prevalence, serotype distribution, and resistance patterns among children on Lombok Island, Indonesia.
2001 Apr 1
Yes-associated protein and p53-binding protein-2 interact through their WW and SH3 domains.
2001 Apr 27
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
Phenotypic and genotypic characterization of antibiotic-resistant Propionibacterium acnes isolated from acne patients attending dermatology clinics in Europe, the U.S.A., Japan and Australia.
2001 Feb
Vibrio parahaemolyticus associated with cholera-like diarrhea among patients in North Jakarta, Indonesia.
2001 Feb
Anti-anaerobic activity of antibacterial agents.
2001 Feb
Resistance patterns of non-O157 Shiga toxin-producing Escherichia coli (STEC) strains isolated from animals, food and asymptomatic human carriers in Switzerland.
2001 Feb
Activity of gatifloxacin and ciprofloxacin in combination with other antimicrobial agents.
2001 Feb
Shigella and Salmonella strains isolated from children under 5 years in Gaborone, Botswana, and their antibiotic susceptibility patterns.
2001 Jan
Clonal relationships among penicillin-susceptible, multiresistant serotype 6B Streptococcus pneumoniae isolates recovered in Greece and France.
2001 Jan
[Pneumococcal antibiotic resistance in 1999. Results from 19 registries for 1999].
2001 Jan
DNA circle formation in Neisseria gonorrhoeae: a possible intermediate in diverse genomic recombination processes.
2001 Jan
Molecular cloning of the guinea pig cytomegalovirus (GPCMV) genome as an infectious bacterial artificial chromosome (BAC) in Escherichia coli.
2001 Jan
In vitro Gram-positive antimicrobial activity of evernimicin (SCH 27899), a novel oligosaccharide, compared with other antimicrobials: a multicentre international trial.
2001 Jan
Rocky Mountain spotted fever and pregnancy: a case report and review of the literature.
2001 Jan
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
Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal.
2001 Jun 1
Analysis of a conserved hydrophobic pocket important for the thermostability of Bacillus pumilus chloramphenicol acetyltransferase (CAT-86).
2001 Mar
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001 Mar
Antimicrobial resistance of Enterococci in Lebanon.
2001 Mar
Factors involved in the (near) anoxic survival time of Cerastoderma edule: associated bacteria vs. endogenous fuel.
2001 Mar
Improved agar diffusion method for detecting residual antimicrobial agents.
2001 Mar
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
Carriage of antibiotic-resistant bacteria by healthy children.
2001 May
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 Mon Oct 21 19:50:03 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:03 UTC 2019
Record UNII
66974FR9Q1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORAMPHENICOL
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
CHLORAMPHENICOL [MI]
Common Name English
CHLOROPTIC-P S.O.P. COMPONENT CHLORAMPHENICOL
Common Name English
NSC-3069
Code English
OPHTHOCHLOR
Brand Name English
CHLOROMYCETIN
Brand Name English
CHLORAMPHENICOL [MART.]
Common Name English
CHLORAMPHENICOL [HSDB]
Common Name English
NSC-16331
Code English
MYCHEL
Brand Name English
CHLORAMPHENICOL COMPONENT OF CHLOROMYXIN
Common Name English
CHLOROPTIC
Brand Name English
CHLORAMPHENICOL [USP-RS]
Common Name English
CHLORAMPHENICOL [WHO-DD]
Common Name English
CHLORAMPHENICOLUM
HPUS   WHO-IP LATIN  
Common Name English
D-THREO-(-)-2,2-DICHLORO-N-(.BETA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-P-NITROPHENETHYL)ACETAMIDE
Common Name English
CHLORAMPHENICOL [GREEN BOOK]
Common Name English
CHLORAMPHENICOL [WHO-IP]
Common Name English
2,2-DICHLORO-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL)ACETAMIDE
Systematic Name English
OPHTHOCORT COMPONENT CHLORAMPHENICOL
Common Name English
CHLORAMPHENICOL [USP]
Common Name English
CHLORAMPHENICOL [INN]
Common Name English
CHLORAMPHENICOL [ORANGE BOOK]
Common Name English
CHLORAMPHENICOL [EP]
Common Name English
CHLORAMPHENICOL COMPONENT OF CHLOROMYCETIN HYDROCORTISONE
Common Name English
CHLORAMPHENICOL COMPONENT OF CHLOROPTIC-P S.O.P.
Common Name English
OPTOMYCIN
Brand Name English
NOVOMYCETIN
Common Name English
CHLORAMPHENICOL [VANDF]
Common Name English
CHLOROMYCETIN HYDROCORTISONE COMPONENT CHLORAMPHENICOL
Common Name English
ELASE-CHLOROMYCETIN COMPONENT CHLORAMPHENICOL
Common Name English
CHLORAMPHENICOL [JAN]
Common Name English
CHLORAMPHENICOL COMPONENT OF ELASE-CHLOROMYCETIN
Common Name English
CHLORAMPHENICOLUM [HPUS]
Common Name English
SYNTHOMYCETIN
Common Name English
CHLORAMPHENICOL [IARC]
Common Name English
CHLORAMPHENICOLUM [WHO-IP LATIN]
Common Name English
AMPHICOL
Brand Name English
CHLORAMPHENICOL COMPONENT OF OPHTHOCORT
Common Name English
CHLOROMYXIN COMPONENT CHLORAMPHENICOL
Common Name English
ECONOCHLOR
Brand Name English
ACETAMIDE, 2,2-DICHLORO-N-(2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL)-, (R-(R*,R*))-
Common Name English
CHLOROFAIR
Brand Name English
Classification Tree Code System Code
WHO-VATC QD10AF03
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
NCI_THESAURUS C258
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ATC G01AA05
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ATC S03AA08
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QD06AX02
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QG01AA55
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QJ01BA01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
CFR 21 CFR 524.390
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
CFR 21 CFR 530.41
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QS03AA08
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ATC D10AF03
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ATC D06AX02
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
CFR 21 CFR 520.390
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
IARC Chloramphenicol
WHO-VATC QJ51BA01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QJ51RB01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QS02AA01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
NDF-RT N0000175479
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
NDF-RT N0000175479
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
CFR 21 CFR 522.390
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ATC J01BA01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
NDF-RT N0000175480
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.2
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QG01AA05
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ATC S01AA01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
CFR 21 CFR 520.390A
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
LIVERTOX 190
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ATC S02AA01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-VATC QS01AA01
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
CFR 21 CFR 520.390B
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
Code System Code Type Description
MESH
D002701
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
CAS
56-75-7
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
INN
977
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
NCI_THESAURUS
C363
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
EPA CompTox
56-75-7
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
LactMed
56-75-7
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
HSDB
56-75-7
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-287-4
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
PUBCHEM
5959
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
DRUG BANK
DB00446
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
MERCK INDEX
M3347
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL130
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
EVMPD
SUB06173MIG
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
WIKIPEDIA
CHLORAMPHENICOL
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
RXCUI
2348
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY RxNorm
Related Record Type Details
METABOLIC ENZYME -> NON-INHIBITOR
METABOLIC ENZYME -> INHIBITOR
COMPETITIVE INHIBITOR
Ki
METABOLIC ENZYME -> INHIBITOR
MIXED INHIBITION
MAJOR
Ki
METABOLIC ENZYME -> NON-INHIBITOR
METABOLIC ENZYME -> NON-INHIBITOR
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
METABOLIC ENZYME->WEAK INHIBITOR
COMPETITIVE INHIBITOR
Ki
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Colourless to greyish white or yellowish white, needle-like crystals or elongated plates or a crystalline powder; odourless.
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC