Generated by DeepSeek V3.2| clindamycin | |
|---|---|
| IUPAC name | (2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide |
| Tradename | Cleocin, Dalacin, others |
| Drugs.com | monograph, clindamycin |
| Routes of administration | By mouth, intravenous, topical, vaginal |
| Bioavailability | 90% (oral) |
| Protein bound | 92–94% |
| Metabolism | Liver |
| Elimination half-life | 2–3 hours |
| Excretion | Bile and urine |
| CAS number | 18323-44-9 |
| PubChem | 29029 |
| ChemSpiderID | 27000 |
| UNII | 3U02EL437C |
| ChEBI | 37456 |
| ChEMBL | 34 |
| ATC prefix | D10 |
| ATC suffix | AF01 |
| ATC supplemental | J01FF01, G01AA10 |
clindamycin is a lincosamide antibiotic used to treat a variety of bacterial infections. It is effective against many anaerobic bacteria, as well as certain Gram-positive bacteria like Staphylococcus aureus and Streptococcus pneumoniae. The medication is available in oral, intravenous, and topical formulations, marketed under brand names such as Cleocin and Dalacin.
Clindamycin is primarily indicated for serious infections caused by susceptible anaerobic bacteria, including those in the Bacteroides and Clostridium genera. It is a key agent for treating aspiration pneumonia, lung abscess, and intra-abdominal infection. For skin and soft tissue infection caused by methicillin-resistant Staphylococcus aureus, it is often used in combination regimens. In dentistry, it is a common alternative for penicillin-allergic patients with severe odontogenic infection. The World Health Organization includes it on its List of Essential Medicines. Topical forms are used for acne vulgaris and bacterial vaginosis.
The most serious adverse effect associated with clindamycin is Clostridioides difficile infection, which can lead to severe pseudomembranous colitis. This risk necessitates cautious prescribing. Common side effects include nausea, vomiting, diarrhea, and abdominal pain. Rash and pruritus may occur, and rare instances of severe hypersensitivity reactions like Stevens-Johnson syndrome have been reported. Intravenous administration can cause thrombophlebitis, and rapid infusion has been linked to cardiac arrest. The U.S. Food and Drug Administration issues warnings regarding its association with C. difficile.
Clindamycin exerts its bacteriostatic effect by binding to the 50S ribosomal subunit of susceptible bacteria, inhibiting protein synthesis. It demonstrates good tissue penetration, achieving high concentrations in bone, joint, and abscess fluid. Metabolism occurs primarily in the liver via the cytochrome P450 system. The drug is excreted through both the bile and urine. Its mechanism is similar to that of other macrolide antibiotics, though it belongs to a distinct chemical class.
Clindamycin was first synthesized in 1966 by scientists at the Upjohn Company, now part of Pfizer. It was developed as a semisynthetic derivative of lincomycin, an antibiotic isolated from the soil bacterium Streptomyces lincolnensis. The modification, involving a chlorine substitution, yielded improved oral bioavailability and a broader antimicrobial spectrum. It received approval from the U.S. Food and Drug Administration in the early 1970s. Its role expanded significantly during the 1980s with the rise of community-associated MRSA infections.
Clindamycin is available as a generic medication and is considered cost-effective in many healthcare systems. Its use is monitored by antimicrobial stewardship programs in institutions like the Centers for Disease Control and Prevention due to its link with C. difficile. In popular culture, it was notably mentioned in the television series *House* regarding a treatment dilemma. The drug is on the World Health Organization Model List of Essential Medicines, underscoring its global clinical importance. Legal cases have involved allegations of failure to warn about the risk of severe colitis.
Category:World Health Organization essential medicines Category:Lincosamides Category:Antibiotics