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Profiles of Drug Substances,... 2019Thiouracil, 2-sulfanylidene-1H-pyrimidin-4-one, has been used as anti-thyroid, coronary vasodilator, and in congestive heart failure. It was found to cause...
Thiouracil, 2-sulfanylidene-1H-pyrimidin-4-one, has been used as anti-thyroid, coronary vasodilator, and in congestive heart failure. It was found to cause agranulocytosis and it is suspected to be teratogenic and carcinogenic. Owing to its high frequency of adverse reactions, especially agranulocytosis, its use was abandoned in favor of other, less toxic drugs, such as propylthiouracil and methimazole. Thiouracil refers both to a specific molecule consisting of a sulfated uracil and a family of molecules based upon the structure. An important member of this family is propylthiouracil, which is a thiourea antithyroid drug that acts by blocking the production of thyroid hormones; it also inhibits the peripheral deiodination of thyroxine to tri-iodothyronine. This profile is prepared to discuss and explain physical and chemical properties, proprietary and nonproprietary names of thiouracil and propylthiouracil. It also includes uses and applications, methods of preparation, thermal and spectral behavior and methods of analysis. In addition, metabolism, excretion and pharmacology of propylthiouracil are also discussed.
Topics: Antithyroid Agents; Methimazole; Propylthiouracil; Thiouracil; Thyroxine
PubMed: 31029221
DOI: 10.1016/bs.podrm.2018.11.006 -
Lancet (London, England) Jun 1947
Topics: Propylthiouracil; Thiouracil
PubMed: 20246545
DOI: No ID Found -
Lancet (London, England) Jun 1947
Topics: Hyperthyroidism; Propylthiouracil; Thiouracil; Thyroid Gland
PubMed: 20343552
DOI: 10.1016/s0140-6736(47)91393-7 -
Annals of Internal Medicine Oct 1948
Topics: Acute Disease; Humans; Inflammation; Thiouracil; Thyroid Gland; Thyroiditis; Thyroiditis, Suppurative
PubMed: 18890273
DOI: 10.7326/0003-4819-29-4-730 -
The Journal of Chemical Physics Feb 2016Ground- and excited-state UV photoelectron spectra of thiouracils (2-thiouracil, 4-thiouracil, and 2,4-dithiouracil) have been simulated using multireference...
Ground- and excited-state UV photoelectron spectra of thiouracils (2-thiouracil, 4-thiouracil, and 2,4-dithiouracil) have been simulated using multireference configuration interaction calculations and Dyson norms as a measure for the photoionization intensity. Except for a constant shift, the calculated spectrum of 2-thiouracil agrees very well with experiment, while no experimental spectra are available for the two other compounds. For all three molecules, the photoelectron spectra show distinct bands due to ionization of the sulphur and oxygen lone pairs and the pyrimidine π system. The excited-state photoelectron spectra of 2-thiouracil show bands at much lower energies than in the ground state spectrum, allowing to monitor the excited-state population in time-resolved UV photoelectron spectroscopy experiments. However, the results also reveal that single-photon ionization probe schemes alone will not allow monitoring all photodynamic processes existing in 2-thiouracil. Especially, due to overlapping bands of singlet and triplet states the clear observation of intersystem crossing will be hampered.
Topics: Models, Chemical; Photoelectron Spectroscopy; Thiouracil
PubMed: 26896982
DOI: 10.1063/1.4941948 -
Food Additives & Contaminants. Part A,... Dec 2021Thiouracil (2-thiouracil) is a thyreostatic compound that can be used as an illegal growth promoter. In bovine, porcine and other farm animals, low concentrations of...
Thiouracil (2-thiouracil) is a thyreostatic compound that can be used as an illegal growth promoter. In bovine, porcine and other farm animals, low concentrations of thiouracil are detected in urine. There is much debate on which concentrations can be considered to originate from feed ('natural') and which concentrations are caused by the illegal administration of thiouracil for growth-promoting purposes. Currently, a threshold value of 10 µg/L in urine is applied. The threshold value is based on epidemiological data. Data on thiouracil from animals treated with thiouracil is scarce. We conducted a study whereby animals were fed with rapeseed, rapeseed with thiouracil, or regular feed with thiouracil (low and high concentration). It was determined that administration of thiouracil leads to concentrations higher than the current 10 µg/L threshold of thiouracil and its metabolites in urine during treatment. Animals fed with rapeseed showed higher thiouracil concentrations than the control group, mostly above 10 µg/L and in some cases above 30 µg/L. In the discovery study, several biomarkers for thiouracil treatment were tentatively identified and confirmed with reference standards. One metabolite was identified as indicative for thiouracil abuse, namely 6-methyl-thiouracil. Another metabolite, 4-thiouracil, was indicative for endogenous formation and did not increase during 2-thiouracil treatment. 6-Methyl-thiouracil was not found in urine samples from the Dutch routine control programmes that contained (endogenous) 2-thiouracil above the threshold value. However, 4-thiouracil was found at high concentrations in the same samples when 2-thiouracil was present. This study's overall conclusion is that the threshold value for thiouracil in bovine urine samples should be set at 10 µg/L and for porcine urine samples at 30 µg/L. Also, confirmation of 6-methyl-thiouracil and 4-thiouracil should be used as indicators for exogenous or endogenous origin in routine control monitoring programmes.
Topics: Animal Feed; Animals; Animals, Domestic; Brassicaceae; Cattle; Food Analysis; Swine; Thiouracil
PubMed: 34477489
DOI: 10.1080/19440049.2021.1967463 -
Science (New York, N.Y.) Sep 1953
Topics: Adrenal Glands; Thiouracil
PubMed: 13089690
DOI: 10.1126/science.118.3063.307-a -
American Practitioner and Digest of... Sep 1947
Topics: Drug-Related Side Effects and Adverse Reactions; Thiouracil
PubMed: 20263187
DOI: No ID Found -
Bollettino Della Societa Italiana Di... Jun 1948
Topics: Thiouracil
PubMed: 18893469
DOI: No ID Found -
Antimicrobial Agents and Chemotherapy Mar 1977A soil organism identified as Streptomyces libani var. soldani was found to produce 4-thiouracil. The product was isolated in a yield of 150 mug/ml of filtered beer and...
A soil organism identified as Streptomyces libani var. soldani was found to produce 4-thiouracil. The product was isolated in a yield of 150 mug/ml of filtered beer and characterized by C-13 magnetic resonance and high-resolution mass spectroscopy. The product has a broad antibacterial spectrum but low specific activity.
Topics: Bacillus subtilis; Fermentation; Microbial Sensitivity Tests; Streptomyces; Thiouracil
PubMed: 404965
DOI: 10.1128/AAC.11.3.569