Thioureas

Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), with the oxygen atom replaced by sulfur atom (as implied by the thio- prefix). The properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the formula

Thiamazole, also known as methimazole, is a medication used to treat hyperthyroidism. This includes Graves' disease, toxic multinodular goiter, and thyrotoxic crisis. It is taken by mouth. Full effects may take a few weeks to occur.

Propylthiouracil (PTU) is a medication used to treat hyperthyroidism. This includes hyperthyroidism due to Graves' disease and toxic multinodular goiter. In a thyrotoxic crisis it is generally more effective than methimazole. Otherwise it is typically only used when methimazole, surgery, and radioactive iodine is not possible. It is taken by mouth.

Phenylthiocarbamide (PTC), also known as phenylthiourea (PTU), is an organosulfur thiourea containing a phenyl ring.

Carbimazole (brand names Neo-Mercazole, Anti-Thyrox, etc.) is used to treat hyperthyroidism. Carbimazole is a pro-drug as after absorption it is converted to the active form, methimazole. Methimazole prevents thyroid peroxidase enzyme from iodinating and coupling the tyrosine residues on thyroglobulin, hence reducing the production of the thyroid hormones T3 and T4 (thyroxine).

Ergothioneine (EGT) is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring. This compound occurs in relatively few organisms, notably actinomycetota, cyanobacteria, and certain fungi. Ergothioneine was discovered by Charles Tanret in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined in 1911.

chemical compound

Methisazone (USAN) or metisazone (INN) is an antiviral drug that works by inhibiting mRNA and protein synthesis, especially in pox viruses. During trials in the 1960s it showed promising results against smallpox infection, but widespread use was considered logistically impractical in the developing countries facing smallpox cases, and it saw only limited use. In developed countries able to cope with the logistic challenge, treatment of smallpox could be achieved just as effectively with immunoglobulin therapy, without the severe nausea associated with metisazone.

Ambazone is an oral antiseptic.

2-Thiouracil is a chemical derivative of uracil in which the oxygen atom in the 2-position of the ring is substituted by sulfur. It is classified as a thiourea.

Thiocarbanilide is an organic chemical compound with the formula (C6H5NH)2CS. This white solid is a derivative of thiourea. It is prepared by the reaction of aniline and carbon disulfide.

Timiperone, sold under the brand name Tolopelon, is a typical antipsychotic of the butyrophenone class which is marketed in Japan for the treatment of schizophrenia. It is similar in chemical structure to benperidol, but has a thiourea group instead of a urea group. It acts as an antagonist for the D2 and 5-HT2A receptors.

Burimamide is an antagonist at the H2 and H3 histamine receptors. At physiological pH, it is largely inactive as an H2 antagonist, but its H3 affinity is 100x higher. It is a thiourea derivative.

Thiocarlide (or tiocarlide or isoxyl) is a thiourea drug used in the treatment of tuberculosis, inhibiting synthesis of oleic acid and tuberculostearic acid.

chemical compound

'''1,1'-Thiocarbonyldiimidazole (TCDI''') is a thiourea containing two imidazole rings. It is the sulfur analog of the peptide coupling reagent carbonyldiimidazole (CDI).

Thiophanate-methyl is an organic compound with the formula C6H4(NHC(S)NH(CO)OCH3)2. The compound is a colorless or white solid, although commercial samples are generally tan-colored. It is prepared from o-phenylenediamine. It is a widely used fungicide used on tree, vine, and root crops. In Europe it is applied to tomato, wine grapes, beans, wheat, and aubergine.

Methylthiouracil is an organosulfur compound that is used antithyroid preparation. It is a thioamide, closely related to propylthiouracil. Methylthiouracil is not used clinically in the United States, it has a similar mechanism of action and side effect to that of propylthiouricil. The drug acts to decrease the formation of stored thyroid hormone, as thyroglobulin in the thyroid gland. The clinical effects of the drug to treat the hyperthyroid state can have a lag period of up to two weeks, depending on the stores of thyroglobulin and other factors.

Sulfathiourea is a sulfonamide antibacterial.

Thioacetazone (INN, BAN), also known as amithiozone (USAN), is an oral antibiotic which is used in the treatment of tuberculosis. It has fallen into almost complete disuse due to toxicity and the introduction of improved anti-tuberculosis drugs like isoniazid. The drug has only weak activity against Mycobacterium tuberculosis and is only useful in preventing resistance to more powerful drugs such as isoniazid and rifampicin. It is never used on its own to treat tuberculosis; it is used in a similar way to ethambutol.

chemical compound

Benzylthiouracil (BTU) is an antithyroid preparation. It is a thioamide, closely related to propylthiouracil.

Monastrol is a cell-permeable small molecule inhibitor discovered by Thomas U. Mayer in the lab of Tim Mitchison. Monastrol was shown to inhibit the kinesin-5 (also known as KIF11, Kinesin Eg5), a motor protein important for spindle bipolarity.

Metiamide is a histamine H2 receptor antagonist developed from another H2 antagonist, burimamide. It was an intermediate compound in the development of the successful anti-ulcer drug cimetidine (Tagamet).

Noxytiolin is an anti-infective used for irrigation of the peritoneum.

(2-Chlorophenyl)thiourea is a chemical compound used as an herbicide. As of 1998, the Environmental Protection Agency did not have it registered as a pesticide in the United States.

Capsazepine is a synthetic antagonist of capsaicin. It is used as a biochemical tool in the study of TRPV ion channels.

Thiocarbohydrazide is a toxic compound made by the reaction of carbon disulfide with hydrazine (hydrazinolysis). It is used in the silver proteinate specific staining of carbohydrates in electron microscopy.

4-Thiouracil is a heterocyclic organic compound having a pyrimidine skeleton. It is a derivative of the nucleobase uracil with a sulfur instead of oxygen in position 4. It is found naturally in the 4-thiouridine nucleoside.

Nepicastat (; developmental code names SYN117, RS-25560-197) is an inhibitor of dopamine β-hydroxylase (DBH), an enzyme that catalyzes the conversion of dopamine to norepinephrine.

chemical compound

thumb|S-Ethylisothiouronium diethylphosphate|S-Ethylisothiouronium diethylphosphate: an example of an isothiuronium compound

Mercaptobenzimidazole is the organosulfur compound with the formula C6H4(NH)2C=S. It is the mercaptan of benzimidazole. It is a white solid that has been investigated as a corrosion inhibitor. The name is a misnomer because the compound is a thiourea, characterized with a short C=S bond length of 169 pm. A similar situation applies to 2-mercaptoimidazole, which is also a thiourea properly called 2-imidazolidinethione and mercaptobenzothiazole, which is also a thioamide.

'''o-Tolylthiourea''' is a highly toxic chemical compound.

chemical compound

Prothioconazole is a synthetic chemical produced primarily for its fungicidal properties. It is a member of the class of compounds triazoles, and possesses a unique toxophore in this class of fungicides. Its effective fungicidal properties can be attributed to its ability to inhibit CYP51A1. This enzyme is required to biosynthesize ergosterol, a key component in the cell membrane of fungi.