26599-17-7
26599-17-7 structure
- Name: Thiarabine
- Chemical Name: 4-Amino-1-(4-thio-β-D-arabinofuranosyl)-2(1H)-pyrimidinone
- CAS Number: 26599-17-7
- Molecular Formula: C9H13N3O4S
- Molecular Weight: 259.282
- Catalog: Signaling Pathways Cell Cycle/DNA Damage DNA/RNA Synthesis
- Create Date: 2017-12-05 16:40:40
- Modify Date: 2024-01-10 19:39:33
-
Thiarabine (OSI-7836) shows potent anti-tumor activity and inhibition of DNA synthesis.
| Name | 4-Amino-1-(4-thio-β-D-arabinofuranosyl)-2(1H)-pyrimidinone |
|---|---|
| Synonyms |
5-Azacytidine,3',5'-tribenzoate
s-Triazin-2(1H)-one,2',3',5'-tribenzoate 2(1H)-Pyrimidinone, 4-amino-1-(4-thio-β-D-arabinofuranosyl)- 2',3',5'-tri-O-benzoyl-5-azacytidine 4-Amino-1-(4-thio-β-D-arabinofuranosyl)-2(1H)-pyrimidinone THIARABINE [(2R,3R,4R,5R)-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate |
| Description | Thiarabine (OSI-7836) shows potent anti-tumor activity and inhibition of DNA synthesis. |
|---|---|
| Related Catalog | |
| Target |
DNA synthesis[1]. |
| In Vivo | Thiarabine has demonstrated exceptional antitumor activity against numerous human tumor xenografts in mice, being superior to gemcitabine, clofarabine, or cytarabine. Unlike cytarabine, Thiarabine demonstrates excellent activity against solid tumor xenografts, suggesting that this agent has the kind of robust activity in animal models that leads to clinical utility. Thiarabine is effective orally (bioavailability of approximately 16%) and with once per day dosing: Two characteristics that distinguish it from cytarabine. Although both the structure and basic mechanism of action of Thiarabine are similar to that of cytarabine, there are many quantitative differences in the biochemical pharmacology of these two agents that can explain the superior antitumor activity of Thiarabine. Two important attributes are the long retention time of the 5'-triphosphate of thiarabine in tumor cells and its potent inhibition of DNA synthesis. The biochemical pharmacology of Thiarabine is also different from that of gemcitabine[1]. |
| References |
| Density | 1.9±0.1 g/cm3 |
|---|---|
| Boiling Point | 535.0±60.0 °C at 760 mmHg |
| Molecular Formula | C9H13N3O4S |
| Molecular Weight | 259.282 |
| Flash Point | 277.4±32.9 °C |
| Exact Mass | 259.062683 |
| PSA | 147.89000 |
| LogP | -1.91 |
| Vapour Pressure | 0.0±3.2 mmHg at 25°C |
| Index of Refraction | 1.814 |
|
~84%
26599-17-7 |
| Literature: Tiwari, Kamal N.; Shortnacy-Fowler, Anita T.; Cappellacci, Loredana; Parker, William B.; Waud, William R.; Montgomery, John A.; Secrist III, John A. Nucleosides, Nucleotides and Nucleic Acids, 2000 , vol. 19, # 1-2 p. 329 - 340 |
| Precursor 1 | |
|---|---|
| DownStream 0 | |