UNCLASSIFIED

ANTIBIOTICS
AVILES, CESLY JEWEL A.
RELUCIO, CRIZZA M.
Chloramphenicol
 Structure-Activity Relationship & MOA
Related to Structure
Modification of p-Nitrophenyl Group:
oIf the nitro group of phenyl ring of chloramphenicol is
replaced by other substituents like NH2, OH, CN, their
physiological activity is reduced or loss.
oReplacement of phenyl group by other aromatic systems or
cyclic systems like cyclohexyl, furyl, naphthyl, pyridyl or
thienyl results in loss of activity or found to be less
effective.
oShifting the nitro group from para position, reduces the
anti-bacterial activity.
 Structure-Activity Relationship & MOA
Related to Structure
Modification of Dichloroacetamide Chain
oIf chloro group is replaced by bromo group, the antibacterial
activity is only 80% .
Modification of 1,3-Propanediol
oThe propane diol group is essential for its antibacterial
activity.
oIf the length of the propane is altered, the drug is deactivated.
oIf the bulkier substituents are introduced activity is
decreased.
 Structure-Activity Relationship & MOA
Related to Structure

Chloramphenicol has two asymmetrical carbon atom.

oIt can form 4 optically active isomers – D & L Threo isomers
and D & L Erythro isomers.
oErythro isomers – toxic & not used in medicine.
oL-Threo isomer – biologically inactive.
oD-Threo isomer – biologically active.
 General Indications
Chloramphenicol is an antibiotic use for
the treatment of a number of bacterial
infections. This includes as an eye
ointment to treat conjunctivitis.

By mouth or by IV, it is used to

treat typhoid, pneumonia, rickettsia,
urinary tract infection, whooping cough,
meningitis, plague, syphilis, gonorrhea,
and dysentery