6-プロピル-2-チオウラシル

外観

白色～わずかにうすい黄色, 粉末

溶解性

水に難溶。水酸化ナトリウム, アンモニアの水溶液に易溶。エタノール, アセトンに微溶、クロロホルム, 水, エーテルに難溶。水酸化ナトリウム溶液に溶け、エタノールにやや溶けにくく、水に極めて溶けにくい。

効能

抗甲状腺薬, 甲状腺ホルモン合成阻害薬

商品名

チウラジール (ニプロESファーマ); プロパジール (あすか製薬)

説明

Propylthiouracil (PTU) is a thioamide antithyroid agent. It inhibits thyroid peroxidase activity in rat and monkey thyroid microsomes (IC₅₀s = 0.081 and 4.1 μM, respectively). PTU (30 mg/kg) increases thyroid weight and serum thyroid stimulating hormone levels and decreases serum 3,5,3''-triiodothyronine and thyroxine levels in rats. Sensitivity to the bitter taste of PTU is genetically mediated and is associated with increased sensitivity to other sweet and bitter compounds. Formulations containing propylthiouracil have been used in the treatment of Graves'' disease and hyperthyroidism.

化学的特性

White Crystalline Powder

定義

ChEBI: A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.

一般的な説明

Propylthiouracil, 6-propyl-2-thiouracil (Propacil), is a stable, white, crystalline powderwith a bitter taste. It is slightly soluble in water but readilysoluble in alkaline solutions (salt formation).

空気と水の反応

Sensitive to light. May be sensitive to prolonged exposure to air. Insoluble in water.

反応プロフィール

Propylthiouracil is incompatible with strong oxidizing agents, strong acids and strong bases. Forms complexes with divalent metals. Reacts with sulfhydryl-oxidizing agents . When reduced will produce hydrogen sulfide.

危険性

Possible carcinogen.

火災危険

Flash point data for Propylthiouracil are not available; however Propylthiouracil is probably combustible.

作用機序

This drug has a pronounced thyrostatic effect and causes reduced thyroxine synthesis in the thyroid gland. It inhibits the process of iodination of thyroglobulin, reduces formation of the active form of iodine in the thyroid gland, and blocks the peroxidase system. Propylthiouracil is used for hyperthyrosis, thyrotoxic crises, and on thyrodectomia. Synonyms of this drug are propycil and tireostat.

臨床応用

Propylthiouracil is useful in the treatment of hyperthyroidism.There is a delay in appearance of its effects because propylthiouracildoes not interfere with the activity of thyroid hormonesalready formed and stored in the thyroid gland. Thislag period may vary from several days to weeks, dependingon the condition of the patient. The need for three equallyspaced doses during a 24-hour period is often stressed, butevidence now indicates that a single daily dose is as effectiveas multiple daily doses in the treatment of most hyperthyroidpatients.

安全性プロファイル

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. Human systemic effects: agranulocytosis, hepatitis, jaundice. Human teratogenic effects by ingestion: developmental abnormalities of the endocrine system and changes in newborn viability. Human and experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SO, and NO,. See also MERCAPTANS.

職業ばく露

Medication (antihyperthyroid; thyroid inhibitor) with human and veterinary applications.

発がん性

Propylthiouracil is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

輸送方法

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

純化方法

Purify propacil by recrystallisation from H2O (soluble in 900 parts at 20o, and 100 parts at 100o). UV, MeOH: max 277nm. [Anderson et al. J Am Chem Soc 67 2197 1945, Vanderhaegue Bull Soc Chim Belg 59 689 1950, Beilstein 24 III/IV 1333.]

不和合性

This chemical is probably combustible; it’s dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanga- nates, perchlorates, chlorine, bromine, fluorine, etc.); con- tact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Forms complexes with divalent metals. Reacts with sulfhydryl-oxidizing agents . Sensitive to light and may be sensitive to air.

廃棄物の処理

It is inappropriate and possi- bly dangerous to the environment to dispose of expired or waste pharmaceuticals by flushing them down the toilet or discarding to trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely pack- age the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.