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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H42Cl2N2O6
Molecular Weight 561.538
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORAMPHENICOL PALMITATE

SMILES

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

InChI

InChIKey=PXKHGMGELZGJQE-ILBGXUMGSA-N
InChI=1S/C27H42Cl2N2O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-24(32)37-20-23(30-27(34)26(28)29)25(33)21-16-18-22(19-17-21)31(35)36/h16-19,23,25-26,33H,2-15,20H2,1H3,(H,30,34)/t23-,25-/m1/s1

HIDE SMILES / InChI

Molecular Formula C27H42Cl2N2O6
Molecular Weight 561.538
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CHLOROPTIC

Cmax

ValueDoseCo-administeredAnalytePopulation
16.9 μg/mL
500 mg 4 times / day multiple, oral
CHLORAMPHENICOL blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
59.1 μg × h/mL
500 mg 4 times / day multiple, oral
CHLORAMPHENICOL blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
500 mg 4 times / day multiple, oral
CHLORAMPHENICOL blood
Homo sapiens
5.1 h
25 mg/kg 4 times / day multiple, intravenous
CHLORAMPHENICOL serum
Homo sapiens
2.2 h
25 mg/kg 4 times / day multiple, intravenous
CHLORAMPHENICOL SUCCINATE serum
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

PubMed

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
Record UNII
43VU4207NW
Record Status Validated (UNII)
Record Version