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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 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
Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation.
1975 Dec
Survey of yeast mastitis in dairy herds of small-type farms in the Lublin region, Poland.
2001
Comparative review of topical ophthalmic antibacterial preparations.
2001
Disposition kinetics of florfenicol in goats by using two analytical methods.
2001 Apr
Strain differences in haematological response to chloramphenicol succinate in mice: implications for toxicological research.
2001 Apr
Streptococcus pneumoniae nasopharyngeal carriage prevalence, serotype distribution, and resistance patterns among children on Lombok Island, Indonesia.
2001 Apr 1
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.
2001 Feb
Phytochemical and antimicrobial properties of constituents of "Ogwu Odenigbo", a popular Nigerian herbal medicine for typhoid fever.
2001 Feb
Activity of gatifloxacin and ciprofloxacin in combination with other antimicrobial agents.
2001 Feb
Antimicrobial resistance of Streptococcus pneumoniae isolates in 1999 and 2000 in Madrid, Spain: a multicentre surveillance study.
2001 Feb
Variable specific activity of Escherichia coli beta-galactosidase in bacterial cells.
2001 Feb 5
A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli.
2001 Jan
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 features determining lymphocyte reactivity in allergic contact dermatitis to chloramphenicol and azidamphenicol.
2001 Jan
Interaction of human aldehyde dehydrogenase with aromatic substrates and ligands.
2001 Jan 30
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
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
Clostridium sordelii corneal ulcer.
2001 Mar-Apr
In vitro susceptibilities to topical antibiotics of bacteria isolated from the surface of clinically symptomatic eyes.
2001 Mar-Apr
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
Carriage of antibiotic-resistant bacteria by healthy children.
2001 May
Neisseria meningitidis with decreased susceptibility to penicillin in Ontario, Canada 1997-2000.
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
Decreased susceptibility to ciprofloxacin in Salmonella enterica serotype typhi, United Kingdom.
2001 May-Jun
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

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
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