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外観
うすい黄色～褐色～暗い緑色粉末～結晶
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解説
C9H5NOClI(305.52)．5-クロロ-7-ヨード-8-キノリノール(5-chloro-7-iodo-8-quinolinol)ともいう．クリオキノールは，淡黄白色～淡黄褐色の軽質の粉末．わずかに特異な臭いを呈する．無味．融点約175 ℃(分解)．熱氷酢酸，ジメチルホルムアミドに易溶，水，エタノールに不溶．光によって徐々に変化する．各種細菌や赤痢アメーバなどの原虫による疾患に有効な内服可能の殺菌剤。腸管からの吸収が少なく、消化管内の殺菌や腸内異常発酵の抑制に有効なため、細菌性の下痢症の治療に腸内殺菌剤、止瀉(ししゃ)剤（下痢どめ）として繁用されたが、1970年（昭和45）スモンの一原因としてその副作用が重大問題となり、医薬品としての製造販売が禁止された。森北出版「化学辞典（第2版）
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効能
抗アメーバ薬, 抗真菌薬
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化学的特性
Almost white, light yellow, brownish-yellow or yellowish-grey powder.
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使用
Clioquinol is used as an anti-infective agent; antiamoebic agent; intravaginal trichomonacide; used to impregnate cotton bandages for antibacterial purposes; in animals as an intestinal anti-infective agent.
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適応症
Iodochlorhydroxyquin (Clioquinol), containing 40% iodine, was originally developed
as a substitute for iodoform as an antiseptic dusting powder. Although its
most effective use is in the treatment of amebiasis, it also has mild antibacterial
and antifungal effects and may be used alone or with steroids in the treatment
of eczematous and impetiginized processes and some dermatophyte, yeast, and
Trichomonas infections. However, more specific agents are available. Because of
neurotoxicity, the oral form of this drug has been withdrawn in the United States.
A recent study demonstrating significant percutaneous absorption when applied to
intact human skin raises concern regarding its topical use as well. The medication
may stain the skin, hair, and clothing yellow and may induce contact allergy.
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定義
ChEBI: A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by chlorine and iodine, respectively. It has antibacterial and atifungal properties, and is used in creams for the treatment of skin infections. It has al
o been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.
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世界保健機関（WHO）
Clioquinol, a halogenated hydroxyquinoline derivative, was
introduced into medicine around 1900 as a topical antiseptic and in 1934 oral
preparations for the treatment of amoebic dysentery and simple diarrhoea became
available. By 1964 its use in Japan had been associated with cases of sub-acute
myelo-optic neuropathy (SMON) which reached epidemic proportions resulting in
its withdrawal there in 1970. Although relatively few cases of SMON were
documented elsewhere, clioquinol was subsequently withdrawn from use in many
countries and placed under prescription control in others. It was phased out
worldwide by the major manufacturer between 1983 and 1985 on grounds of
obsolescence. No adequately controlled evidence was ever generated to
demonstrate that clioquinol is effective in bacterial or viral diarrhoea. However,
products containing clioquinol and related halogenated hydroxyquinolines
continue to be used in some tropical and subtropical countries where amoebiasis
remains endemic. Other amoebocides are preferred in the WHO Model List of
Essential Drugs.
(Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977)
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一般的な説明
Cream-colored to brownish-yellow powder. Practically odorless. Decomposes at 178-179°C. Used as a topical anti-infective.
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空気と水の反応
Insoluble in water.
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反応プロフィール
Clioquinol is incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides . Darkens on exposure to light.
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火災危険
Flash point data for Clioquinol are not available; however, Clioquinol is probably combustible.
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臨床応用
5-Chloro-7-iodo-8-quinolinol, 5-chloro8-hydroxy-7-iodoquinoline, or iodochlorhydroxyquin (Vioform) occursas a spongy, light-sensitive, yellowish white powder that isinsoluble in water. Vioform was initially used as a substitutefor iodoform in the belief that it released iodine in the tissues.It has been used as a powder for many skin conditions,such as atopic dermatitis, eczema, psoriasis, and impetigo.A 3% ointment or cream has been used vaginally as a treatmentfor Trichomonas vaginalis vaginitis. The best use forVioform is in the topical treatment of fungal infections suchas athlete’s foot and jock itch. A combination with hydrocortisone(Vioform HC) is also available.
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安全性プロファイル
Poison by ingestion.
Moderately toxic by intraperitoneal route.
Human systemic effects by ingestion:
change in central nervous system electrical
function, optic nerve damage, and changes
in vision. Experimental teratogenic and
reproductive effects. Human mutation data
reported. When heated to decomposition it
emits very toxic fumes of Cl-, I-, and NOx.
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純化方法
It crystallises from AcOH or xylene and dry it at 70o in vacuo.[Beilstein 21 III/IV 1190.]
