クリンダマイシン

解説

C18H33ClN2O5S(424.99)．放線菌の産生するリンコマイシンを塩基スルフィニルで塩化すると得られる7-クロロ誘導体．クリンダマイシンは，黄色の無定形固体．[α]_D＋21.4°(クロロホルム)．塩酸塩·一水和物は融点141～143 ℃．[α]²⁵_D＋144°(水)．細菌のリボソームの50Sサブユニットの23S rRNAに結合して，ペプチド転移反応を抑え，タンパク質合成を阻害する．グラム陽性菌，グラム陰性菌，マイコプラズマ，リケッチア，クラミジア感染症に有効である．塩酸塩，または2位のリン酸エステル誘導体が注射，内服，または外用で使用される．LD50 245 mg/kg(マウス，静注)．[CAS 18323-44-9][CAS 58207-19-5:塩酸塩·H2O][CAS 24729-96-2:リン酸エステル]森北出版「化学辞典（第2版）

効能

抗生物質, タンパク質合成阻害薬

説明

Clindamycin, a derivative of lincomycin, was first isolated from Streptomyces lincolnesis in 1962 and became commercially available in 1966. The name originates from Lincoln, Nebraska, where the organism was first isolated from a soil sample. The parent compound of clindamycin is lincomycin, which is produced by actinomycete, Streptomyces liconelnensis, which belongs to the order of Actinobacteria. It replaced lincomycin use because of its better absorption and clinical spectrum. Lincomycin belongs to the lincosamides, which is a class of antibiotics. The compounds use as antibiotic agents stems from their ability to interfere with the protein synthesis of bacteria. The chemical modification of lincomycin, clindamycin, has proven to be superior to the natural product for clinical applications. Clindamycin is better absorbed from the gastrointestinal tract and food does not interfere with its absorption. It is also eight times more active against aerobic gram-positive cocci, and it has proven activity against gram-positive and gram-negative anaerobic bacteria as well as protozoal organisms like Toxoplasma and Plasmodium species.

使用

Clindamycin is a semi-synthetic analogue of lincomycin, prepared by chloride substitution of the exocyclic sugar hydroxy group. This affords a more hydrophobic compound with improved pharmacodynamics. Like other members of the lincosamide family, clindamycin is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Clindamycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Clindamycin has been extensively studied with over 8,000 literature citations.

定義

ChEBI: Clindamycin is a carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic. The physiologic effect of clindamycin is by means of Decreased Sebaceous Gland Activity, and Neuromuscular Blockade.

適応症

Clindamycin (Cleocin), 300 to 450 mg/day, is an extremely effective agent for acne.

接触アレルゲン

This lincosanide antibiotic is used in topical form for acne, or systemically has been responsible for exanthematous rashes and acute generalized exanthematous pustulosis.

作用機序

Clindamycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit. The use of clindamycin with macrolides is not recommended since both of them compete for binding sites to the 50S subunit.

臨床応用

Clindamycin is effective in the treatment of most infections secondary to anaerobes and gram-positive cocci. It can be used for anaerobic pulmonary, intra-abdominal, gynecologic, pelvic, diabetic foot, and decubitus ulcer infections. Another appropriate agent should be added since the majority of these infections are polymicrobial. It can also be used as an alternative agent for patients with severe penicillin allergy. It is also used to treat Clostridium perfringens infection.
Oral preparations of clindamycin and vaginal cream are alternatives to metronidazole for the treatment of bacterial vaginosis. Topical solution is used for treatment of acne vulgaris and rosacea.
Clindamycin is extensively metabolized by the liver and the half-life is prolonged in patients with cirrhosis and hepatitis. Dose reductions are recommended in patients with acute liver disease.

副作用

The most commonly observed adverse effect is diarrhea. The reported incidence of C. difficile colitis in patients treated with clindamycin varies from 0.1 to 10%. The syndrome may be fatal. If the patient develops C. difficile colitis, clindamycin should be discontinued and the patient should be treated for C. difficile . Other side effects include rash, nausea, vomiting, diarrhea, flatulence, abdominal distension, anorexia, and transient elevation of liver enzymes. Other less common events, such as fever, neutropenia, thrombocytopenia, and eosinophilia have been reported.