クロルテトラサイクリン

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Warning

• 危険有害性情報

  H302：飲み込むと有害

• 注意書き

  P264：取扱い後は皮膚をよく洗うこと。

  P264：取扱い後は手や顔をよく洗うこと。

  P270：この製品を使用する時に、飲食または喫煙をしないこ と。

  P301+P312：飲み込んだ場合：気分が悪い時は医師に連絡する こと。

  P330：口をすすぐこと。

  P501：内容物/容器を．．．に廃棄すること。

クロルテトラサイクリン 価格

MSDS Information

• 7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide

クロルテトラサイクリン 化学特性,用途語,生産方法

• 解説

  クロルテトラサイクリン．オーレオマイシンともいう．Streptomyces aureofaciensが産生するテトラサイクリン系抗生物質の一つ．テトラサイクリンより，7位が塩素化されているクロルテトラサイクリンのほうが抗菌力が3～4倍強い．黄色の結晶．融点168～169 ℃．[α]_D²³－275°(メタノール)．UV(0.1 mol L－1 塩酸)λmax 230，262.5，367.5 nm．水，エタノール，ベンゼンに可溶，エーテルに不溶．グラム陽性菌，グラム陰性菌，マイコプラズマ，リケッチア．クラミジアなど広範囲の抗菌スペクトルを示し，経口または外用で使用される．テトラサイクリン系抗生物質としては，半合成品であるドキシサイクリンや，ミノサイクリンも経口または静注で使用されている．LD50 10 g/kg(ラット，経口)．

• 効能

  抗生物質, 抗原虫薬, タンパク質合成阻害薬

• 説明

  Chlortetracycline (Brand name: Aureomycin) is the 7-chloro substitution derivative of the tetracycline and has a golden color. As a veterinary medicine, chlortetracycline is commonly used for the treatment of conjunctivitis of cats. It can also be used in the treatment of infections occurring in the urinary tract, respiratory tract, and the intestines. Its mechanism of action is through inhibiting the protein synthesis, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex through binding to the 30S ribosome subunit.

• 化学的特性

  Golden-yellow crystalline powder, odorless with a bitter taste; decomposes at a melting point of 168-169°C. Slightly soluble in water but soluble in saline solutions. The hydrochloride form is slightly soluble in methanol, water, and ethanol and insoluble in acetone, ether, and chloroform. Stable in air, but the colour gradually darkens upon exposure to light.

• 使用

  Chlortetracycline was the first reported member of the tetracycline class, isolated from Streptomyces aureofaciens in 1948. Chlortetracyclines heralded the early wave of antibiotic discoveries from microbes and after 50 years are still widely used as pharmaceuticals. Chlortetracycline is a pigment and, like most pigments, is extremely sensitive to environmental and storage conditions. Commercial chlortetracycline may contain significant levels of degradation products.

• 定義

  ChEBI: Chlortetracycline is a member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens. It has a role as an antiprotozoal drug, a fluorescent probe, a calcium ionophore and an antibacterial drug. It is a member of monochlorobenzenes, a tertiary amino compound, a tertiary alcohol, a monocarboxylic acid amide, a tertiary alpha-hydroxy ketone and a member of tetracyclines. It is a conjugate acid of a chlortetracycline(1-).

• 適応症

  Chlorotetracycline, an antibiotic with a broad spectrum of action, causes a bacteriostatic effect with respect to Gram-positive (staphylococci, including those that produce penicillinase; streptococci, pneumococci; clostridia, listeria, and anthrax bacillus) and Gram-negative microorganisms (gonococci, whooping cough bacillus, colon bacillus, enterobacteria, klebisella, salmonella, shigella), as well as Rickettsia, chlamydia, mycoplasma, and spirochaeta. Blue-pus bacillus, proteus, serracia, most strains of Bacteroides fragilis, most fungi, and small viruses are resistant to this drug. It is used for pneumonia, bronchitis, empyema of the lungs, angina, cholecystitis, whooping cough, endocarditis, endometritis, intestinal infections, prostatitis, syphilis, gonorrhea, brucellosis, osteomyelitis, purulent infections of soft tissues, and others caused by microorganisms sensitive to this drug. Synonyms of this drug are aureomycin, biomycin, xanthomycin, and others.

• 抗菌性

  It is slightly less active than tetracycline against many bacteria, with the exception of Gram-positive organisms.

• 応用例（製薬）

  7-Chlortetracycline. A fermentation product of certain strains of Streptomyces aureofaciens. Formulated as the hydrochloride or the free base for oral or topical application.

• 薬物動態学

  Oral absorption：30–60%
  C_max 500 mg oral：2.5–7 mg/L：
  Plasma half-life： 5–6 h
  Volume of distribution： c.2 L/kg
  Plasma protein binding： 47–65%
  Absorption is relatively poor compared with other tetracyclines. It undergoes rapid metabolism and is largely eliminated by biliary excretion, with only a small proportion eliminated via the kidney. Despite this, chlortetracycline is not recommended for patients in renal failure, since accumulation occurs as a consequence of the half-life increase to approximately 7–11 h.

• 臨床応用

  Its uses are those common to the group. It has also been used topically in the management of recurrent aphthous ulcers of the mouth, but experience is limited and the mechanism of action is unknown.

• 副作用

  Side effects are typical of the group. Contact hypersensitivity has been reported with topical application to abraded skin and varicose ulcers.

• 安全性プロファイル

  Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cland NOx. See also TETRACYCLINE.

• 純化方法

  Aureomycin is dehydrated by azeotropic distillation of its solution with toluene. On cooling, the anhydrous material crystallises out and is recrystallised from *C6H6, then dried under vacuum at 100o over paraffin wax. (If it is crystallised from MeOH, it contains MeOH which is not removed on drying.) [Stephens et al. J Am Chem Soc 76 3568 1954, Laskin & Chan Biochem Biophys Res Commun 14 137 1964]. [Beilstein 14 IV 2631.]

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