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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H12Cl2N2O5.C4H6O4.C2H7NO
Molecular Weight 502.301
Optical Activity UNSPECIFIED
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 No
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 No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CHLOROPTIC

Approved Use

Indications 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 Date

1968
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16.9 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
59.1 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
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
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
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

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 0.5 - 12 years
Sex: unknown
Sources:
Other AEs: Swollen eyelid...
Other AEs:
Swollen eyelid (1 patient)
Sources:
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
Health Status: unhealthy
Age Group: 11 years
Sex: F
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
Sources:
unhealthy, 15 years
Health Status: unhealthy
Age Group: 15 years
Sex: F
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
Health Status: unhealthy
Age Group: 23 years
Sex: M
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
Health Status: unhealthy
Age Group: 27 years
Sex: F
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
Health Status: unhealthy
Age Group: 39 years
Sex: M
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
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: M
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
Health Status: unhealthy
Age Group: 61 years
Sex: M
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
Health Status: unhealthy
Age Group: 68 years
Sex: F
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
Health Status: unhealthy
Age Group: 71 years
Sex: F
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
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 0.5 - 12 years
Sex: unknown
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
Health Status: unhealthy
Age Group: 11 years
Sex: F
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
Sources:
unhealthy, 15 years
Health Status: unhealthy
Age Group: 15 years
Sex: F
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
Health Status: unhealthy
Age Group: 23 years
Sex: M
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
Health Status: unhealthy
Age Group: 27 years
Sex: F
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
Health Status: unhealthy
Age Group: 39 years
Sex: M
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
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: M
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
Health Status: unhealthy
Age Group: 61 years
Sex: M
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
Health Status: unhealthy
Age Group: 68 years
Sex: F
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
Health Status: unhealthy
Age Group: 71 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
UV-induced increase in RNA polymerase activity in Xanthomonas oryzae pathovar oryzae.
2001-08
A novel heat shock protein plays an important role in thermal stress management in cyanobacteria.
2001-07-06
Antibacterial activity of 4,5-dihydroxy-2-cyclopentan-1-one (DHCP) and cloning of a gene conferring DHCP resistance in Escherichia coli.
2001-07
Decreased susceptibility to ciprofloxacin in Salmonella enterica serotype typhi, United Kingdom.
2001-06-01
Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal.
2001-06-01
Cloning and functional analysis of a phosphopantetheinyl transferase superfamily gene associated with jadomycin biosynthesis in Streptomyces venezuelae ISP5230.
2001-06
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.
2001-06
External quality assessment of antimicrobial susceptibility testing in Europe.
2001-06
Screening of antibiotic resistant inhibitors from local plant materials against two different strains of Pseudomonas aeruginosa.
2001-06
Drug resistant Haemophilus influenzae from respiratory tract infection in a tertiary care hospital in north India.
2001-05-24
Clinical prevalence, antimicrobial susceptibility, and geographic resistance patterns of enterococci: results from the SENTRY Antimicrobial Surveillance Program, 1997-1999.
2001-05-15
Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999.
2001-05-15
Methicillin-resistant staphylococci and ofloxacin-resistant bacteria from clinically healthy conjunctivas.
2001-05-08
Clostridium sordelii corneal ulcer.
2001-05-08
Neisseria meningitidis with decreased susceptibility to penicillin in Ontario, Canada 1997-2000.
2001-05-01
Successful treatment of vancomycin-resistant Enterococcus endocarditis with oral linezolid.
2001-05-01
Increased mitochondrial-encoded gene transcription in immortal DF-1 cells.
2001-05-01
Induction of complement sensitivity in Escherichia coli by citric acid and low pH.
2001-05
Natural antibiotic susceptibility of Klebsiella pneumoniae, K. oxytoca, K. planticola, K. ornithinolytica and K. terrigena strains.
2001-05
In vitro susceptibility of Vibrio spp. isolated from the environment.
2001-05
High prevalence of carriage of antibiotic-resistant Streptococcus pneumoniae in children in Kampala Uganda.
2001-05
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.
2001-05
Carriage of antibiotic-resistant bacteria by healthy children.
2001-05
Comparative study of the influence of melatonin and vitamin E on the surface characteristics of Escherichia coli.
2001-05
Plasmid transfer and susceptibility to antibiotics in the halophilic phototrophs Rhodovibrio salinarum and Rhodothalassium salexigens.
2001-04-01
Disposition kinetics of florfenicol in goats by using two analytical methods.
2001-04
Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait.
2001-04
Antimicrobial resistance of Streptococcus pneumoniae at a university hospital in Saudi Arabia.
2001-04
Strain differences in haematological response to chloramphenicol succinate in mice: implications for toxicological research.
2001-04
Randomised controlled trial of ketorolac in the management of corneal abrasions.
2001-04
[Susceptibility of non-typhi Salmonella spp. at the Galdakao Hospital (1992-1998)].
2001-03
Analysis of a conserved hydrophobic pocket important for the thermostability of Bacillus pumilus chloramphenicol acetyltransferase (CAT-86).
2001-03
Occurrence of the vanA and vanC2/C3 genes in Enterococcus species isolated from poultry sources in Malaysia.
2001-03
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001-03
Antimicrobial susceptibility of Listeria monocytogenes isolated from meningoencephalitis in sheep.
2001-03
Antimicrobial resistance of Enterococci in Lebanon.
2001-03
Liposome-mediated DNA uptake and transient expression in Thermotoga.
2001-02
Molecular epidemiology of multiple drug resistant type 6B Streptococcus pneumoniae in the Northern Territory and Queensland, Australia.
2001-02
Interaction of human aldehyde dehydrogenase with aromatic substrates and ligands.
2001-01-30
A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli.
2001-01
Chloramphenicol treatment for vancomycin-resistant Enterococcus faecium bacteremia.
2001-01
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
Prevalence of serotypes and molecular epidemiology of Streptococcus pneumoniae strains isolated from children in Beijing, China: identification of two novel multiply-resistant clones.
2001
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center.
2001
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
Variation in clonality and antibiotic-resistance genes among multiresistant Salmonella enterica serotype typhimurium phage-type U302 (MR U302) from humans, animals, and foods.
2001
Patents

Sample Use Guides

Chloramphenicol 0.5% Eye Drops
Route of Administration: Topical
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 Mar 31 18:10:24 GMT 2025
Edited
by admin
on Mon Mar 31 18:10:24 GMT 2025
Record UNII
FMO6OC31WV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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)
Preferred Name English
CHLORAMPHENICOL MONOETHANOLAMINE SUCCINATE
Common 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
PUBCHEM
131801044
Created by admin on Mon Mar 31 18:10:24 GMT 2025 , Edited by admin on Mon Mar 31 18:10:24 GMT 2025
PRIMARY
FDA UNII
FMO6OC31WV
Created by admin on Mon Mar 31 18:10:24 GMT 2025 , Edited by admin on Mon Mar 31 18:10:24 GMT 2025
PRIMARY
CAS
20369-85-1
Created by admin on Mon Mar 31 18:10:24 GMT 2025 , Edited by admin on Mon Mar 31 18:10:24 GMT 2025
PRIMARY
Related Record Type Details
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