| Identification | More | [Name]
THIONICOTINAMIDE | [CAS]
4621-66-3 | [Synonyms]
3-PYRIDYLTHIOCARBOXAMIDE AKOS B028584 ART-CHEM-BB B028584 PYRIDINE-3-CARBOTHIOAMIDE PYRIDINE-3-CARBOTHIOIC ACID AMIDE PYRIDINE-3-THIOAMIDE THIONICOTINAMIDE 3-pyridinecarbothioamide 3-pyridinethiocarboxamide 3-pyridylthioformamide 3-thioamidopyridine 3-thiocarbamoylpyridine nicotinothioamide thio-3-pyridinecarboxamide thio-nicotinamid Pyridine-3-thiocarboxamide Thionicotinamide,98% PYRIDINE-3-THIOCARBOXAMIDE (THIONICOTINAMIDE) Nicotinthioamide | [EINECS(EC#)]
225-036-6 | [Molecular Formula]
C6H6N2S | [MDL Number]
MFCD00006399 | [Molecular Weight]
138.19 | [MOL File]
4621-66-3.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow powder | [Melting point ]
185-190 °C
| [Boiling point ]
278.9±32.0 °C(Predicted) | [density ]
1.235 (estimate) | [refractive index ]
1.5300 (estimate) | [Fp ]
160 °C
| [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Powder | [pka]
12.01±0.29(Predicted) | [color ]
Yellow to yellow-green | [Detection Methods]
HPLC,NMR | [BRN ]
109593 | [InChI]
InChI=1S/C6H6N2S/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9) | [InChIKey]
XQWBMZWDJAZPPX-UHFFFAOYSA-N | [SMILES]
C1=NC=CC=C1C(N)=S | [LogP]
0.670 | [CAS DataBase Reference]
4621-66-3(CAS DataBase Reference) | [EPA Substance Registry System]
3-Pyridinecarbothioamide (4621-66-3) |
| Hazard Information | Back Directory | [Chemical Properties]
yellow powder | [Uses]
Thionicotinamide (TN) is an NADK inhibitor prodrug and lead compound[2]. As a lead compound, thionicotinamide sensitizes CEM-CCRF, MOLT-4, RL, and C85 cell lines to chemotherapeutic agents and reduces cellular NADP/NADPH pools[2][3]. | [Definition]
Thionicotinamide is the active moiety of two previously identified NADK inhibitors, NADS and NADPS. Treatment of C85 cancer cells with thionicotinamide resulted in an identical loss of dihydrofolate reductase levels, a G1/S block, and similar toxicity profiles as NADS and NADPS; that is, thionicotinamide is a prodrug and is converted intracellularly to NADPS[1].
| [in vivo]
In vivo administration of thionicotinamide at 100 mg/kg every other day significantly reduces tumor growth in C85 xenografts (four cycles) and RL diffuse large B-cell lymphoma xenografts (five cycles) without observed neurotoxicity or weight loss[3]. | [References]
[1] Philip M Tedeschi. “Suppression of Cytosolic NADPH Pool by Thionicotinamide Increases Oxidative Stress and Synergizes with Chemotherapy.” Molecular Pharmacology 88 4 (2015): 720–7.
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