Chlolincocin;Cleocin;Cleocin Hcl;Cleocin Pediatric;Cleocin Phosphate;Cleocin T;Cleocin T Gel;Cleocin T Lotion;Cleocin T Topical Solution;Clinda-Derm;Clindagel;Clindesse;Clindets;Clinimycin;Dalacin;Dalacin C;Dalacin C Flavored Granules;Dalacin C Phosphate;Dalacin T Topical Solution;Evoclin;ResiDerm A;Sobelin;Zindaclin;

Clindamicina [INN-Spanish];clindamycin;Clindamycin Hcl;Clindamycin Hydrochloride;Clindamycin Phosphate;Clindamycine [French];Clindamycine [INN-French];Clindamycinum [INN-Latin];

Clindamycin is a semisynthetic lincosamide antibiotic that has largely replaced lincomycin due to an improved side effect profile. Clindamycin inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits. It may be bacteriostatic or bactericidal depending on the organism and drug concentration.

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Synthesis Reference

Not Available

General Reference

Daum RS: Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus. N Engl J Med. 2007 Jul 26;357(4):380-90. Pubmed Klempner MS, Styrt B: Clindamycin uptake by human neutrophils. J Infect Dis. 1981 Nov;144(5):472-9. Pubmed Lamont RF: Can antibiotics prevent preterm birth—the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed Plaisance KI, Drusano GL, Forrest A, Townsend RJ, Standiford HC: Pharmacokinetic evaluation of two dosage regimens of clindamycin phosphate. Antimicrob Agents Chemother. 1989 May;33(5):618-20. Pubmed

Type	small molecule

Classes

Glycerol and Derivatives Pyrans

Substructures

Glycerol and Derivatives Hydroxy Compounds Pyrans Amino Ketones Pyrrolidines Ethers Carboxylic Acids and Derivatives Aliphatic and Aryl Amines Alkyl Halides Alcohols and Polyols Heterocyclic compounds Carboxamides and Derivatives Acetals and Derivatives

antibacterials 抗细菌;

Indication	For the treatment of serious infections caused by susceptible anaerobic bacteria, including Bacteroides spp., Peptostreptococcus, anaerobic streptococci, Clostridium spp., and microaerophilic streptococci. May be useful in polymicrobic infections such as intra-abdominal or pelvic infections, osteomyelitis, diabetic foot ulcers, aspiration pneumonia and dental infections. May also be used to treat MSSA and respiratory infections caused by S. pneumoniae and S. pyogenes in patients who are intolerant to other indicated antibiotics or who are infected with resistant organism. May be used vaginally to treat vaginosis caused by Gardnerella vaginosa. Clindamycin reduces the toxin producing effects of S. aureus and S. pyogenes and as such, may be particularly useful for treating necrotizing fasciitis. May be used topically to treat acne.
Pharmacodynamics	Clindamycin is an antibiotic, similar to and a derivative of lincomycin. Clindamycin can be used in topical or systemic treatment. It is effective as an anti-anaerobic antibiotic and antiprotozoal.
Mechanism of action	Systemic/vaginal clindamycin inhibits protein synthesis of bacteria by binding to the 50S ribosomal subunits of the bacteria. Specifically, it binds primarily to the 23s RNA subunit. Topical clindamycin reduces free fatty acid concentrations on the skin and suppresses the growth of Propionibacterium acnes (Corynebacterium acnes) , an anaerobe found in sebaceous glands and follicles.
Absorption	Rapidly absorbed after oral administration with peak serum concentrations observed after about 45 minutes. Absorption of an oral dose is virtually complete (90%) and the concomitant intake of food does not appreciably modify the serum concentrations; serum levels have been uniform and predictable from person to person and dose to dose. Clindamycin does not penetrate the blood brain barrier.
Volume of distribution	Not Available
Protein binding	92-94%
Metabolism	Hepatic
Route of elimination	Approximately 10% of the bioactivity is excreted in the urine and 3.6% in the feces; the remainder is excreted as bioinactive metabolites.
Half life	2.4 hours
Clearance	Not Available
Toxicity	Adverse effects include nausea (may be dose-limiting), diarrhea, pseudomembranous colitis, allergic reactions, hepatoxicity, transient neutropenia and eosinophilia and agranulocytosis. Pseudomembranous colitis occurs in 0.01 - 10% of patients and occurs more commonly than with other antibiotics. Use of the topical formulation of clindamycin results in absorption of the antibiotic from the skin surface. Diarrhea, bloody diarrhea, and colitis (including pseudomembranous colitis) have been reported with the use of topical and systemic clindamycin.
Affected organisms	Enteric bacteria and other eubacteria
Pathways	Pathway Name SMPDB ID Clindamycin Pathway SMP00249

Properties
State	solid
Experimental Properties	Property Value Source melting point 142 [HCl salt] Not Available water solubility 30.6 mg/L Not Available logP 2.16 HANSCH,C ET AL. (1995)
Predicted Properties	Property Value Source water solubility 3.10e+00 g/l ALOGPS logP 1.76 ALOGPS logP 1.04 ChemAxon logS -2.1 ALOGPS pKa (strongest acidic) 12.16 ChemAxon pKa (strongest basic) 7.55 ChemAxon physiological charge 1 ChemAxon hydrogen acceptor count 6 ChemAxon hydrogen donor count 4 ChemAxon polar surface area 102.26 ChemAxon rotatable bond count 7 ChemAxon refractivity 105.72 ChemAxon polarizability 44.49 ChemAxon

Drug	Interaction
Aluminium	The aluminium salt decreases the absorption of lincosamides
Atracurium	The agent increases the effect of muscle relaxant
Attapulgite	The aluminium salt decreases the absorption of lincosamides
Cyclosporine	Clindamycin may decrease the therapeutic effect of cyclosporine.
Dihydroxyaluminium	The aluminium salt decreases the absorption of lincosamides
Doxacurium chloride	The agent increases the effect of muscle relaxant
Kaolin	The aluminium salt decreases the absorption of lincosamides
Metocurine	The agent increases the effect of muscle relaxant
Mivacurium	The agent increases the effect of muscle relaxant
Pancuronium	The agent increases the effect of muscle relaxant
Pipecuronium	The agent increases the effect of muscle relaxant
Rocuronium	The agent increases the effect of muscle relaxant
Succinylcholine	The agent increases the effect of muscle relaxant
Tubocurarine	The agent increases the effect of muscle relaxant
Vecuronium	The agent increases the effect of muscle relaxant

• Take with food.