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Clindamycin (Molecule of the Month for February 2010)

Dalacin, Duac, BenzaClin, Clindoxyl, Acanya



Clindamycin is an antibiotic. It is usually used to treat infections with anaerobic bacteria but can also be used to treat some protozoal diseases, such as malaria. It is a common topical treatment for acne and can be useful against some methicillin-resistant Staphylococcus aureus (MRSA) infections.

Clindamycin is used primarily to treat anaerobic infections caused by susceptible anaerobic bacteria, including dental infections, and infections of the respiratory tract, skin and soft tissue infections, and peritonitis. In patients with hypersensitivity to penicillins, clindamycin may be used to treat infections caused by susceptible aerobic bacteria as well. It is also used to treat bone and joint infections, particularly those caused by Staphylococcus aureus. Topical application of clindamycin phosphate can be used to treat mild to moderate acne. Multiple studies have shown the use of clindamycin in conjunction with benzoyl peroxide, which is available both through prescription or over-the-counter, to be more effective in the treatment of acne than the use of either product by itself Given with chloroquine or quinine, clindamycin is effective and well-tolerated in treating Plasmodium falciparum malaria; the latter combination is particularly useful for children, and is the treatment of choice for pregnant women who become infected in areas where resistance to chloroquine is common.

The most severe common adverse effect of clindamycin is Clostridium difficile-associated diarrhea (the most frequent cause of pseudomembranous colitis). Although this side-effect occurs with almost all antibiotics, including beta-lactam antibiotics, it is classically linked to clindamycin use.Pseudomembranous colitis, a cause of antibiotic-associated diarrhea (AAD), is an infection of the colon. It is often, but not always, caused by the bacterium Clostridium difficile. Because of this, the informal name C. difficile colitis is also commonly used. The illness is characterized by offensive-smelling diarrhea, fever, and abdominal pain. In severe cases, life-threatening complications can develop, such as toxic megacolon. The use of clindamycin, broad-spectrum antibiotics such as cephalosporins or any penicillin based antibiotic such as amoxicillin causes the normal bacterial flora of the bowel to be altered. In particular, when the antibiotic kills off other competing bacteria in the intestine, any bacteria remaining will have less competition for space and nutrients there. The net effect is to permit much more extensive growth than normal of certain bacteria. Clostridium difficile is one such type of bacterium. In addition to proliferating in the bowel, C. difficile also produces toxins. Without either Toxin A or Toxin B, C. difficile may colonize the gut but is unlikely to cause pseudomembranous colitis

Formal Chemical Name (IUPAC)
(2S,4R)-N-{2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide

References

http://en.wikipedia.org/wiki/Clindamycin

http://en.wikipedia.org/wiki/Pseudomembranous_colitis

Picture of Clindamycin 3D model

click on the picture of  Clindamycin above to interact
with the 3D model of the
Clindamycin structure
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Picture of Clindamycin

C18 H33 Cl N2 O5 S



Update by Karl Harrison
(Molecule of the Month for February 2010 )

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