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

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 C4H6O4
Molecular Weight 118.088
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 C2H7NO
Molecular Weight 61.0831
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
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...
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
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)
120 mg/kg/day
Sources:
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
nafcillin
Sources:
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

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
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)
120 mg/kg/day
Sources:
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
nafcillin
Sources:
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Survey of yeast mastitis in dairy herds of small-type farms in the Lublin region, Poland.
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
Comparative review of topical ophthalmic antibacterial preparations.
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
Intraabdominal vancomycin-resistant enterococcus infections: the new threat.
2001 Apr
Toxicity of natural tear substitutes in a fully defined culture model of human corneal epithelial cells.
2001 Apr
Activity of moxifloxacin against clinical isolates of Streptococcus pneumoniae from England and Wales.
2001 Apr
Plasmid transfer and susceptibility to antibiotics in the halophilic phototrophs Rhodovibrio salinarum and Rhodothalassium salexigens.
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
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.
2001 Feb
Determination of assay and impurities of gamma irradiated chloramphenicol in eye ointment.
2001 Feb
Effect of highly bioaccumulated polychlorinated biphenyl congeners on estrogen and androgen receptor activity.
2001 Feb 14
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
Inactivation of chloramphenicol by Staphylococcus aureus biotype C from humans & animals.
2001 Jan
Interaction of human aldehyde dehydrogenase with aromatic substrates and ligands.
2001 Jan 30
Lack of evidence for chloramphenicol resistance in Neisseria meningitidis, Africa.
2001 Jan-Feb
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 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
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
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
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 Fri Dec 15 15:50:11 GMT 2023
Edited
by admin
on Fri Dec 15 15:50:11 GMT 2023
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
PUBCHEM
131801044
Created by admin on Fri Dec 15 15:50:11 GMT 2023 , Edited by admin on Fri Dec 15 15:50:11 GMT 2023
PRIMARY
FDA UNII
FMO6OC31WV
Created by admin on Fri Dec 15 15:50:11 GMT 2023 , Edited by admin on Fri Dec 15 15:50:11 GMT 2023
PRIMARY
CAS
20369-85-1
Created by admin on Fri Dec 15 15:50:11 GMT 2023 , Edited by admin on Fri Dec 15 15:50:11 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE