51-52-5 Usage
Description
Propylthiouracil (PTU), also known as 6-propyl-2-thiouracil (Propacil), is a stable, white, crystalline powder with a bitter taste. It is slightly soluble in water but readily soluble in alkaline solutions, making it a versatile compound for various applications. PTU is a thioamide antithyroid agent that inhibits thyroid peroxidase activity, leading to increased thyroid weight and altered hormone levels in rats. Its sensitivity to the bitter taste is genetically mediated and associated with increased sensitivity to other sweet and bitter compounds.
Uses
Used in Pharmaceutical Industry:
Propylthiouracil is used as an antihyperthyroid agent for the treatment of hyperthyroidism and Graves' disease. It helps in reducing the overproduction of thyroid hormones, thus alleviating the symptoms of hyperthyroidism.
Used in Agricultural Industry:
Propylthiouracil has been used to promote fattening in animals, as it can help in controlling the metabolic rate and improving the overall growth and health of the animals.
Used in Antimicrobial Applications:
Propylthiouracil is also used as an antibacterial agent, demonstrating its potential in combating bacterial infections.
However, it is important to note that this substance is reasonably anticipated to be a human carcinogen, which may limit its use in certain applications and industries. Further research and development are necessary to explore safer alternatives or to mitigate the potential risks associated with its use.
Air & Water Reactions
Sensitive to light. May be sensitive to prolonged exposure to air. Insoluble in water.
Reactivity Profile
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.
Hazard
Possible carcinogen.
Fire Hazard
Flash point data for Propylthiouracil are not available; however Propylthiouracil is probably combustible.
Biochem/physiol Actions
6-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 action
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.
Clinical Use
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.
Safety Profile
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.
Synthesis
Propylthiouracil, 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
ethoxide.
Potential Exposure
Medication (antihyperthyroid; thyroid
inhibitor) with human and veterinary applications.
Drug interactions
Potentially hazardous interactions with other drugs
None known
Carcinogenicity
Propylthiouracil is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
Metabolism
Propylthiouracil undergoes rapid first-pass metabolism
in the liver, and is mainly excreted in the urine as the
glucuronic acid conjugate, with very little excreted as
unchanged drug.
Shipping
UN3249 Medicine, solid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
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.]
Incompatibilities
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.
Waste Disposal
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.
Check Digit Verification of cas no
The CAS Registry Mumber 51-52-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 51-52:
(4*5)+(3*1)+(2*5)+(1*2)=35
35 % 10 = 5
So 51-52-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H10N2OS/c1-2-4-9-5-3-6(10)8-7(9)11/h3,5H,2,4H2,1H3,(H,8,10,11)
51-52-5Relevant articles and documents
Design, synthesis, and acaricidal activity of phenyl methoxyacrylates containing 2-alkenylthiopyrimidine
Hao, Shulin,Cai, Zengfei,Cao, Yangyang,Du, Xiaohua
, (2020/09/16)
A series of novel phenyl methoxyacrylate derivatives containing a 2-alkenylthiopyrimidine substructure were designed, synthesized, and evaluated in terms of acaricidal activity. The structures of the title compounds were identified by 1H NMR, 13C NMR and high-resolution mass spectra (HRMS). Compound (E)-methyl 2-(2-((2-(3,3-dichloroallylthio)-6-(trifluoromethyl)pyrimidin-4-yloxy) methyl)phenyl)-3-methoxyacr-ylate (4j) exhibited significant acaricidal activity against Tetranychus cinnabarinus (T. cinnabarinus) in greenhouse tests possessing nearly twice the larvicidal and ovicidal activity compared to fluacrypyrim. Furthermore, the results of the field trials demonstrated that compound 4j could effectively control Panonychuscitri with long-lasting persistence and rapid action. The toxicology data in terms of LD50 value confirmed that compound 4j has a relatively low acute toxicity to mammals, birds, and honeybees.
Synthesis and evaluation of 5,6-disubstituted thiopyrimidine aryl aminothiazoles as inhibitors of the calcium-activated chloride channel TMEM16A/Ano1
Piechowicz, Katarzyna A.,Truong, Eric C.,Javed, Kashif M.,Chaney, Rachelle R.,Wu, Johnny Y.,Phuan, Puay W.,Verkman, Alan S.,Anderson, Marc O.
, p. 1362 - 1368 (2016/10/09)
Transmembrane protein 16A (TMEM16A), also called Ano1, is a Ca2+ activated Cl? channel expressed widely in mammalian epithelia, as well as in vascular smooth muscle and some tumors and electrically excitable cells. TMEM16A inhibitors have potential utility for treatment of disorders of epithelial fluid and mucus secretion, hypertension, some cancers and other diseases. 4-Aryl-2-amino thiazole T16Ainh-01 was previously identified by high-throughput screening. Here, a library of 47 compounds were prepared that explored the 5,6-disubstituted pyrimidine scaffold found in T16Ainh-01. TMEM16A inhibition activity was measured using fluorescence plate reader and short-circuit current assays. We found that very little structural variation of T16Ainh-01 was tolerated, with most compounds showing no activity at 10 μM. The most potent compound in the series, 9bo, which substitutes 4-methoxyphenyl in T16Ainh-01 with 2-thiophene, had IC50 ~1 μM for inhibition of TMEM16A chloride conductance.
Identification of novel, exosite-binding matrix metalloproteinase-13 inhibitor scaffolds
Roth, Joshua,Minond, Dmitriy,Darout, Etzer,Liu, Qin,Lauer, Janelle,Hodder, Peter,Fields, Gregg B.,Roush, William R.
scheme or table, p. 7180 - 7184 (2012/01/15)
Matrix metalloproteinase-13 (MMP-13) has been implicated as the protease responsible for collagen degradation in cartilage during osteoarthritis (OA). Compounds that inhibit the metalloproteinase at the Zn binding site typically lack specificity among MMP family members. Analogs of the low-micromolar lead MMP-13 inhibitor 4, discovered through high-throughput screening, were synthesized to investigate structure-activity relationships in this inhibitor series. Systematic modifications of 4 led to the discovery of MMP-13 inhibitors 20 and 24 which are more selective than 4 against other MMPs. Compound 20 is also approximately fivefold more potent as an MMP-13 inhibitor than the original HTS-derived lead compound 4.