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Triapine

Names

[ CAS No. ]:
200933-27-3

[ Name ]:
Triapine

[Synonym ]:
2-[(3-Amino-2-pyridinyl)methylene]hydrazinecarbothioamide
2-[(3-Aminopyridin-2-yl)methylene]hydrazinecarbothioamide
Triapine
Hydrazinecarbothioamide, 2-[(3-amino-2-pyridinyl)methylene]-
2-[(3-Amino-2-pyridinyl)methylene]hydrazinecarbothioamide

Biological Activity

[Description]:

(E)-3-AP is the E configuration of 3-AP. 3-AP is a potent ribonucleotide reductase inhibitor. 3-AP shows anti-proliferative activity. 3-AP shows anticancer activity in L1210 leukemia model. 3-AP inhibits RR activity and DNA synthesis[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vitro]

3-AP shows anti-proliferative activity with IC50 values of 1.3, 1.6 µM for L1210, L1210/HUr cells, respectively[1]. 3-AP (5, 10, 15, 20, 30 mg/kg; i.p.; twice daily for six consecutive days) significantly increases in life span were observed with each dosage employed and long term survivors[1].

[References]

[1]. Finch RA, et al. Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone; 3-AP): an inhibitor of ribonucleotide reductase with antineoplastic activity. Adv Enzyme Regul. 1999;39:3-12.

[2]. Enyedy ÉA ,et al. Complex formation and cytotoxicity of Triapine derivatives: a comparative solution study on the effect of the chalcogen atom and NH-methylation. Dalton Trans. 2020 Dec 8;49(46):16887-16902.

Chemical & Physical Properties

[ Density]:
1.46

[ Boiling Point ]:
436.0±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C7H9N5S

[ Molecular Weight ]:
195.245

[ Flash Point ]:
217.5±31.5 °C

[ Exact Mass ]:
195.057861

[ PSA ]:
125.95000

[ LogP ]:
0.98

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.720

[ Storage condition ]:
-20℃

Related Compounds