Clindamycin Drug - Medicinal Chemistry & Uses

By: Pharma Tips | Views: 6354 | Date: 25-Oct-2011

Clindamycin belongs to a class called Lincomycins which were isolated from Streptomyces. This class resembles another antibiotic class called Macrolides and is active against both gram negative, gram positive bacteria, and anaerobes.

Introduction to Clindamycin:

Clindamycin belongs to a class called Lincomycins which were isolated from Streptomyces.  This class resembles another antibiotic class called Macrolides and is active against both gram negative, gram positive bacteria, and anaerobes. Lincomycins show cross-resistance with other Macrolides and StreptoGramins because they bind to the ribosome in the same way.  Lincomycins are water soluble and when given as a HCl salt they are able to distribute to other body tissues.

Clindamycin

Mechanism of Action:

The Lincomycins, like the Macrolides, are bacteriostatic. They act by binding to the 50S ribosomal subunit and causing the release of a fragmentary peptide by preventing the translocation of peptidyl-tRNA from the A-site to the P-site. By inducing formation of these incomplete peptides, the growth of the bacterial cell is inhibited.

Resistance:

The main mechanism of bacterial resistance to clindamycin is through a modification of ribosomes that results from the methylation of a purine or a mutation of adenine to guanine on the 50S subunit of the ribosome. These modified ribosomes are less efficient at making proteins, but they also reduce binding of the drug. With the reduced binding, clindamycin cannot exert its antibacterial effects.

Important Dispensing Information for Clindamycin:

Clinical Use of Clindamycin:

Clindamycin is FDA approved for the treatment of bacterial infections due to Staphylococcus aureus, Staphylococcus epidermidis, and Streptococcus pyogenes, as well as for the treatment of acne vulgaris, bacterial vaginosis, and pelvic inflammatory disease.

Dose and Dosage Forms:

Clindamycin is available for oral, intravenous, parenteral, topical, or vaginal administration. No dose adjustment is necessary for renal failure. Doses should be reduced in patients with liver disease.

Adverse Effects:

The most common adverse effects reported with clindamycin use are diarrhea, nausea, and rash. In rare cases, clindamycin may cause pseudomembranous enterocolitis. Clindamycin may also affect the liver, resulting in jaundice and increased liver function tests. Clindamycin is contraindicated in patients with an allergy to clindamycin or lincomycin.

Drug Interactions:

A well-documented drug interaction exists between Clindamycin and Erythromycin. Coadministration of these drugs may result in cardiotoxicity. QT prolongation, torsades de pointes, and cardiac arrest have been reported in patients taking both drugs. In addition, a probable drug interaction exists between Clindamycin and neuromuscular blocking agents such as Atracurium, Metocurine, and Tubocurarine. Coadministration may result in an prolongation of the neuromuscular blockade. Patients taking these drugs should be monitored closely, and a dose adjustment may be warranted.

Clindamycin is pregnancy category B.

Future Uses:

Clindamycin will continue to be used in the future for the treatment of acne.  According to Foye’s Principles of Medicinal Chemistry, Clindamycin “has excellent activity against Propionobacterium acnes” and it is white so that it can be tinted to match skin tones much better than tetracyclines can.  The future of Clindamycin will be confined to the area of dermatology, because it has been associated with high incidences of pseudomembranous colitis that arises due to the toxins of Clostridium difficile and can cause damage to the intestinal lining.  Furthermore, resistance that develops to Macrolides and Streptogramins will also crossover to Lincomycins, since all three classes act on the same area of the ribosome. Clindamycin will continued to be prescribed in the future, but for limited uses.

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