| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H8N2O2S2 |
| Molecular Weight | 228.291 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(=O)C(NC(C)=O)=C2SSC=C12
InChI
InChIKey=MHMRAFONCSQAIA-UHFFFAOYSA-N
InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
| Molecular Formula | C8H8N2O2S2 |
| Molecular Weight | 228.291 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Thiolutin is a naturally occurring bicyclic dithiole that was first isolated from Streptomyces luteorectiuli based on its antibiotic activities. Thiolutin inhibits the growth of Saccharomyces cerevisiae and several gram-positive and -negative bacteria by inhibiting DNA-dependent RNA polymerases. It also inhibits the adhesion of endothelial cells, including adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin, and restricts tumor cell-induced angiogenesis.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Sample Use Guides
At concentrations as low as 2 mug/ml, the thiolutin inhibited ribonucleic acid (RNA) and protein synthesis in whole cells and spheroplasts. At these low concentrations, protein synthesis continued for a short period of time after RNA synthesis was completely stopped. With higher drug concentrations (greater than 20 mug/ml) protein synthesis was inhibited; concentrations of thiolutin up to 100 mug/ml did not affect translocation or peptide bond formation in cell-free protein-synthesizing systems from yeast. The effect of thiolutin on the activity of partially purified deoxyribonucleic acid-dependent RNA polymerases was examined, and the drug was found to be a potent inhibitor of RNA synthesis in vitro