Chloramphenicol & Clindamycin

Chloramphenicol & Clindamycin

1. Chloramphenicol Agnihotri College of Pharmacy, Wardha Presented by…… Abhijit N. Daf Assistant Professor of Pharmaceutical Chemistry 1

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 2

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 Mechanism of Action 3

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 grou p 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. 4

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 . 5

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 6

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 7

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 8

9. Thank You 9