Chloramphenicol & Clindamycin

1. Agnihotri College of Pharmacy, Wardha
Presented by……
Abhijit N. Daf
Assistant Professor of Pharmaceutical Chemistry
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2. Introduction
 Chloramphenicol was initially obtained from
Streptomyces venezuela
 It was synthesized chemically and commercial
product now its all synthetic
 It has a nitrobenzene substitution, which is probably
responsible for the antibacterial activity and its
intensely bitter taste.
Chloramphenicol
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3. Chloramphenicol is a yellowish white-needle like crystals, slightly
soluble in water, very soluble in alcohol.
It has no odor, but has a very bitter taste.
It possesses two chiral carbon atoms in the acylamido propandiol
chain.
Properties
It inhibits protein synthesis in
bacteria
It acts primarily by binding
reversibly to the 50s ribosomal
subunit
To prevent the binding of the
amino acid containing end of
aminoacyl tRNA to the acceptor
site on the 50s ribosomal subunit
Mechanism of Action
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4. SAR
Replacement of –NO2 group with a number of other substituents like –
CN,CONH2,NH2,OH or various heterocyclic groups resulted in some reduction
or complete loss of antibacterial activity.
Shifting of the – NO2 group from para position reduces the antibacterial
activity.
When phenyl group is replaced by other aromatic or alicyclic groups like
naphthyl,cyclohexyl, etc. they are less potent than chloramphenicol.
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5. The primary alcohol group is required since its replacement with –H or
alkyl group leads to compounds with much less potent activity.
Uses
Chloramphenicol is an important drug of choice for the treatment of
typhoid fever caused by Salmonella typhi.
It is also effective against most bacteria, Haemophilus influenzae.
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6. Clindamycin Or Lincomycin
Lincomycins are sulfur containing antibiotics isolated from
Streptomyces lincolensis.
Lincomycin is the most active and medicinally useful compounds
Structural modification of lincomycin resulted in 7-Chloro-7-
deoxy derivative called Clindamycin.
Clindamycin posses great antibacterial potency, when compare to
Lincomycin
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7. Cont…
 They are active against Gram-positive bacteria, particularly
Cocci & also effective against Non-spore forming anaerobic
bacteria, actinomycetes, mycoplasma.
MOA
Lincomycin
Clindamycin Ribosomes
Binds to 50s ribosomal
subunit to inhibits protein
synthesis
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8. Structural comparison of Lincomycin
& Clindamycin
Lincomycin
 Replacement of 7-Hydroxy group of lincomycin with chlorine it
gives clindamycin with enhanced antibacterial activity
It is available as crystalline, water soluble hydrochloride hydrate.
Clindamycin palmitate hydrochloride salt in oral dosage form as well
as clindamycin phosphate ester in solution for IM or IV inj. Is also
available
USES- It is use as a wide variety of upper respiratory, skin & tissue
infection. It is active against Streptococci, Staphylocci
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9. Thank You
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