| 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)
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 |
|---|---|---|---|
| 20.0 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sourcing
PubMed
Patents
Sample Use Guides
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).
ACTIVE MOIETY
