Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H4N2OS |
| Molecular Weight | 128.152 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC(=S)NC=C1
InChI
InChIKey=ZEMGGZBWXRYJHK-UHFFFAOYSA-N
InChI=1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
| Molecular Formula | C4H4N2OS |
| Molecular Weight | 128.152 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Thiouracil or 2-thiouracil was introduced in 1943 as the first thionamide anti-thyroid drug. Owing to a high frequency of adverse reactions, especially agranulocytosis, use of thiouracil was abandoned in favor of other, less toxic drugs. Thiouracil is not currently used as a thyrostatic drug in humans. Thiouracil inhibits thyroid activity by blocking the enzyme thyroid peroxidase. It is also it is a highly selective inhibitor of neuronal nitric oxide synthase, by interfering with the substrate- and tetrahydrobiopterin (BH(4))-binding to the enzyme. Due to its ability selectively accumulating in de novo-synthesized melanin in overactive melanin-producing cells and thus providing a means to localize melanoma cells, thiouracil can represent a useful new tool to identify modulators of human hair pigmentation.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P07202|||Q8TCI9 Gene ID: 7173.0 Gene Symbol: TPO Target Organism: Homo sapiens (Human) |
|||
Target ID: P29475 Gene ID: 4842.0 Gene Symbol: NOS1 Target Organism: Homo sapiens (Human) |
20.0 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Development of selective agonists and antagonists of P2Y receptors. | 2009-03 |
|
| Effects of primers containing sulfur and phosphate monomers on bonding type IV gold alloy. | 2008-08 |
|
| Analysis of thyreostatic drugs in thyroid samples by ultra-performance liquid chromatography tandem mass spectrometry detection. | 2008-06-09 |
|
| Study of the base discrimination ability of DNA and 2'-O-methylated RNA oligomers containing 2-thiouracil bases towards complementary RNA or DNA strands and their application to single base mismatch detection. | 2008-06-01 |
|
| Effects of primers containing thiouracil and phosphate monomers on bonding of resin to Ag-Pd-Au alloy. | 2008-01 |
|
| Thyroxine increases the rate but does not alter the pattern of innervation during embryonic chick corneal development. | 2008-01 |
|
| Synthesis and characterization of some pyrimidine, purine, amino acid and mixed ligand complexes. | 2008-01 |
|
| Solid-phase synthesis of pseudo-complementary peptide nucleic acids. | 2008 |
|
| RNA analysis by biosynthetic tagging using 4-thiouracil and uracil phosphoribosyltransferase. | 2008 |
|
| Simultaneous inference for ratios of linear combinations of general linear model parameters. | 2007-12 |
|
| Preparation for posterior partial veneered restoration to maintain vertical dimension of occlusion. | 2007-11-01 |
|
| Utility of 6-amino-2-thiouracil as a precursor for the synthesis of bioactive pyrimidine derivatives. | 2007-09-15 |
|
| Atherogenic diet induced diabetes mellitus: involvement of thyroid hormones. | 2007-09-10 |
|
| Effect of metal priming agents on bond strength of resin-modified glass ionomers joined to gold alloy. | 2007-09 |
|
| Experimental hypothyroidism inhibits delta-aminolevulinate dehydratase activity in neonatal rat blood and liver. | 2007-09 |
|
| Simultaneous preconcentration of copper, nickel, cobalt and lead ions prior to their flame atomic absorption spectrometric determination. | 2007-08-19 |
|
| [Vasculitis with renal involvement and antineutrophil cytoplasmic antibodies (ANCA) in a child receiving benzylthiouracil]. | 2007-07 |
|
| Spectral properties of some metal complexes derived from uracil-thiouracil and citrazinic acid compounds. | 2007-07 |
|
| Structure-activity relationship of uridine 5'-diphosphoglucose analogues as agonists of the human P2Y14 receptor. | 2007-05-03 |
|
| Extent of metal ion-sulfur binding in complexes of thiouracil nucleosides and nucleotides in aqueous solution. | 2007-04 |
|
| The impact of thyroid activity variations on some oxidizing-stress parameters in rats. | 2007-02 |
|
| A novel approach for simultaneous determination of 2-mercaptobenzimidazole and derivatives of 2-thiouracil in animal tissue by gas chromatography/mass spectrometry. | 2007 |
|
| Modulation of 5-fluorouracil host-toxicity and chemotherapeutic efficacy against human colon tumors by 5-(Phenylthio)acyclouridine, a uridine phosphorylase inhibitor. | 2006-11 |
|
| Evidence that urinary excretion of thiouracil in adult bovine submitted to a cruciferous diet can give erroneous indications of the possible illegal use of thyrostats in meat production. | 2006-10 |
|
| Synthesis of cell-permeable peptide nucleic acids and characterization of their hybridization and uptake properties. | 2006-09-15 |
|
| Intra- and intermolecular interactions in small bioactive molecules: cooperative features from experimental and theoretical charge-density analysis. | 2006-08 |
|
| Is it safe to treat hyperthyroid patients with I-131 without fear of thyroid storm? | 2006-07 |
|
| ANCA-associated diffuse alveolar hemorrhage due to benzylthiouracil. | 2006-07 |
|
| Evaluation of 2 thione primers and 3 resin adhesives for silver-palladium-copper-gold alloy bonding. | 2006-05 |
|
| An analytical method to screen for six thyreostatic drug residues in the thyroid gland and muscle tissues of food producing animals by liquid chromatography with ultraviolet absorption detection and liquid chromatography/mass spectrometry. | 2006-04-28 |
|
| Flow injection analysis system equipped with a newly designed electrochemiluminescent detector and its application for detection of 2-thiouracil. | 2006-03-01 |
|
| Gas-phase deprotonation of uracil-Cu2+ and thiouracil-Cu2+ complexes. | 2006-02-09 |
|
| Influence of thioketo substitution on the properties of uracil and its noncovalent interactions with alkali metal ions: threshold collision-induced dissociation and theoretical studies. | 2006-02-02 |
|
| Interaction of thioamides, selenoamides, and amides with diiodine. | 2006 |
|
| Reactions Between Chalcogen Donors and Dihalogens/Interalogens: Typology of Products and Their Characterization by FT-Raman Spectroscopy. | 2006 |
|
| Bioinorganic chemistry in thyroid gland: effect of antithyroid drugs on peroxidase-catalyzed oxidation and iodination reactions. | 2006 |
|
| Highly efficient strand invasion by peptide nucleic acid bearing optically pure lysine residues in its backbone. | 2006 |
|
| Unambiguous identification of thiouracil residue in urine collected in non-treated bovine by tandem and high-resolution mass spectrometry. | 2006 |
|
| Thyroid hormone stimulates gamma-glutamyl transpeptidase in the developing rat cerebra and in astroglial cultures. | 2005-12-15 |
|
| Effect of metal conditioner application on bond strength of luting cements to a noble metal. | 2005-12 |
|
| Synthesis of new 2-thiouracil-5-sulphonamide derivatives with antibacterial and antifungal activity. | 2005-11 |
|
| Different approaches for assaying melanosome transfer. | 2005-10 |
|
| UV-induced generation of rare tautomers of 2-thiouracils: a matrix isolation study. | 2005-09-01 |
|
| Synthesis of new 4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives with an incorporated thiazolidinone moiety and testing their possible serine protease and cercarial elastase inhibitory effects with a possible prospective to block penetration of Schistosoma mansoni cercariae into the mice skin. | 2005-09 |
|
| Unrestricted accessibility of short oligonucleotides to RNA. | 2005-09 |
|
| 2,4-dithiouracil: the reproducible H-bonded structural motifs in the complexes with 18-membered crown ethers. | 2005-08-21 |
|
| Unimolecular photochemistry of 4-thiouracils. | 2005-06-23 |
|
| Microplates with integrated oxygen sensors for kinetic cell respiration measurement and cytotoxicity testing in primary and secondary cell lines. | 2005-06 |
|
| SNPs analysis by use of oligonucleotides containing 2'-O-methyl-2-thiouridines. | 2005 |
|
| Condensation of nucleobases at mercury/aqueous solution interface--a structural perspective using hydrogen bonding considerations. | 2002-06-01 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Thiouracil was introduced in 1943 as the first thionamide anti-thyroid drug. The usual dose was 1–2 g/day in divided doses. Owing to a high frequency of adverse reactions, especially agranulocytosis, its use was abandoned in favor of other, less toxic drugs, such as propylthiouracil and methimazole. Thiouracil is not currently used as a thyrostatic drug in humans.
The usual dose was 1–2 g/day in divided doses.
Route of Administration:
Oral
Quantitative analysis of [14C]-2-TU (thiouracil) incorporation showed a significant increase in pigmented hair follicles upon stimulation with 1 uM forskolin concomitant to an increase in tyrosinase levels. A strong significant decrease in [14C]-2-TU incorporation was noted, when hair follicles were incubated with the tyrosinase competitive inhibitor kojic acid (200 uM). Incubation with the MC1-R agonist a-MSH (0.2 uM) did not induce a significant stimulation of hair melanogenesis. Human hair follicles were microdissected from temporal region biopsies obtained from dark hair caucasian female volunteers (>48 years old) after informed consent, for assays on non-pigmented HF versus fully pigmented HF, for assays with kojic acid (donor 1 and a 48-year-old woman). Isolated fully pigmented, grey and non-pigmented human hair follicles were incubated with compounds of interest for various durations in William’s E medium supplemented with 3 uCi ⁄ml [14C]-2-Thiouracil (60 mCi ⁄mmol).
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 17:56:03 GMT 2025
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| Record UNII |
59X161SCYL
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| Record Status |
Validated (UNII)
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C29574
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CHEMBL345768
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m10790
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THIOURACIL
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348530
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C29856
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19473
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