ChemicalBook > Product Catalog > API > Hormones and the Endocrine System > Thyroid hormone and antithyroid drugs > Propylthiouracil
Propylthiouracil Chemical Properties
- Melting point:218-220 °C (lit.)
- Density 1.1880 (rough estimate)
- refractive index 1.5960 (estimate)
- Flash point:300 °C
- storage temp. 2-8°C
- solubility 1.1g/l
- pkapKa 7.8; 8.3 (Uncertain)
- form neat
- PH6-7.5 (5g/l, H2O, 20℃)(slurry)
- Water Solubility 1.1 g/L
- Merck 14,7869
- BRN 130039
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases. Light sensitive.
- CAS DataBase Reference51-52-5(CAS DataBase Reference)
- NIST Chemistry ReferenceTegretol(51-52-5)
- IARC2B (Vol. Sup 7, 79) 2001
- EPA Substance Registry SystemPropylthiouracil (51-52-5)
Propylthiouracil Usage And Synthesis
- DescriptionPropylthiouracil (PTU) is a thioamide antithyroid agent.1 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.2 Formulations containing propylthiouracil have been used in the treatment of Graves'' disease and hyperthyroidism.
- Chemical PropertiesWhite Crystalline Powder
- Chemical PropertiesWhite crystalline solid or powder. Odorless. Bitter taste.
- UsesAntihyperthyroid. Has been used to promote fattening. This substance is reasonably anticipated to be a human carcinogen
- UsesAntihyperthyroid. Has been used to promote fattening. This substance is reasonably anticipated to be a human carcinogen.
- DefinitionChEBI: 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.
- General DescriptionOdorless white crystalline powder of starch-like appearance. Bitter taste. Saturated solution is neutral or slightly acid to litmus.
- General DescriptionPropylthiouracil, 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).
- Air & Water ReactionsSensitive to light. May be sensitive to prolonged exposure to air. Insoluble in water.
- Reactivity ProfilePropylthiouracil 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.
- HazardPossible carcinogen.
- Fire HazardFlash point data for Propylthiouracil are not available; however Propylthiouracil is probably combustible.
- Biochem/physiol Actions6-Propyl-2-thiouracil (6-PTU), a potential inhibitor of D1 iodothyronine deiodinase, is involved in the deiodination of iodothyronines. It is an uncompetitive inhibitor of iodothyronine substrates.
- Mechanism of actionThis 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.
- Clinical UsePropylthiouracil 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.
- Safety ProfileConfirmed 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.
- Chemical SynthesisPropylthiouracil, 6-propyl-2-thio-2,4-(1H,3H)-pyrimidindione (25.2.2),
is synthesized by condensating ethyl butyroacetate with thiourea in the presence of sodium
- Potential ExposureMedication (antihyperthyroid; thyroid inhibitor) with human and veterinary applications.
- CarcinogenicityPropylthiouracil is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
- ShippingUN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- Purification MethodsPurify 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.]
- IncompatibilitiesThis 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.
- Waste DisposalIt 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.
Malathion 2-Thiobarbituric acid CHLOROPHOSPHONAZO III Propylthiouracil Sodium thioglycolate Potassium thioacetate AURORA 12615 4-CYCLOHEXYL-2-MERCAPTO-6-OXO-1,6-DIHYDROPYRIMIDINE-5-CARBONITRILE RARECHEM AL BZ 1246 Propylthiouracil-D5 RARECHEM AL BW 0965 BUTTPARK 116\40-75 2-(METHYLSULFANYL)-5,6,7,8-TETRAHYDRO-4-QUINAZOLINOL BUTTPARK 116\40-70 Propylthiouracil N-b-D-Glucuronide,Propylthiouracil N--D-Glucuronide RARECHEM AL BO 0929 POTASSIUM THIOGLYCOLATE 6-Mercaptopurine
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