Methyl-6-amino-7-chloro-6,7,8-trideoxy- N - [(2 S , 4 R ) -1-methyl-4-propylprolyl] -1-thio-β- L - threo - D - galactooctopyranoside ( IUPAC )
|Molecular formula||C 18 H 33 ClN 2 O 5 S|
|External identifiers / databases|
|Mechanism of action||
Protein synthesis inhibitors
|Molar mass||424.98 g mol −1|
141–143 ° C (hydrochloride monohydrate)
|pK s value||
7.6 (hydrochloride monohydrate)
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .|
Clindamycin has a bacteriostatic effect in the usual dose , and in high doses it is also bactericidal, mainly against gram-positive aerobic germs such as streptococci or staphylococci , against anaerobes , especially gram-negative ones and also against chlamydia . In combination with pyrimethamine , it is effective against Toxoplasma gondii .
Mechanism of action
Like macrolides, clindamycin binds to the 50-S subunit of the (prokaryotic) ribosomes to inhibit protein synthesis in bacteria . Because of the identical mechanism of action, there is sometimes cross-resistance.
Clindamycin is approximately 90% absorbed after oral ingestion and 92–94% is bound to plasma proteins. The plasma half-life is 2.4 hours. In addition to the internal organs, it also reaches the pleural fluid , synovia , bone marrow , milk and skin . The antibiotic also penetrates the placenta . It is remodeled in the liver and excreted in the urine and faeces .
In medicine, clindamycin is mainly used for abscessing pneumonia , osteomyelitis of the diabetic foot ( malum perforans ), chronic osteomyelitis with Staphylococcus aureus , infections of the oral cavity and acne . The field of application of this lincosamide is largely similar to that of the more compatible macrolides , except for staphylococcal infections, whereas macrolides are largely ineffective. Furthermore, clindamycin is a substitute drug for patients with penicillin allergy.
In veterinary medicine, it is also used for severe skin infections ( pyoderma ), respiratory tract infections or eye infections.
Side effects and contraindications
Clindamycin mainly has gastrointestinal side effects such as vomiting, diarrhea and stomach cramps. Drug-related pseudomembranous colitis (inflammation of the colon) is particularly dangerous . This occurs much more frequently with clindamycin than with other antibiotics, but less often and milder than with the related lincomycin. Clostridium difficile -related and serious adverse effects should always lead to discontinuation of clindamycin. Itching , vaginal catarrh ( vaginal discharge ) and exfoliating blistering skin inflammation are mentioned as rather rare side effects . It is also contraindicated during breastfeeding due to the high level of excretion in breast milk.
In herbivores such as horses , ruminants , rabbits , hamsters , guinea pigs , chinchillas , gerbils and bush rats , the drug can cause fatal colitis due to resistant clostridia , which is why clindamycin can only be used in these animals under strict indications and close monitoring.
Interactions with other substances
Due to physical incompatibility, joint parenteral administration with theophylline , barbiturates , calcium gluconate and phenytoin is excluded. Clindamycin may increase the effects of muscle relaxants due to its neuromuscular blockade ; this can lead to life-threatening incidents during anesthesia.
Basocin (D), Clindasol (D), Clindac (A), Clinda-Saar (D), Clin-Sanorania (D), Dalacin (A, CH), Dentomycin (D), Jutaclin (D), Lanacine (A) , Sobelin (D), Turimycin (D), Zindaclin (D, A), numerous generics (D, A, CH)
Veterinary medicine: aniclindan, Antirobe, Cleorobe, Clinacin, Clinda, Permycin
Duac (D, CH), Indoxyl (A)
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