thionicotinamide

amino-3-pyridylmethane-1-thione

CAS: 4621-66-3 C6 H6 N2 S MW: 138.19282000

Identification

Namethionicotinamide
IUPACpyridine-3-carbothioamide
CAS Number4621-66-3
EINECS225-036-6
FDA UNII6A0HXX0753
Molecular FormulaC6 H6 N2 S
Molecular Weight138.19282000
MDL NumberMFCD00006399
Nikkaji NumberJ124.097H
Beilstein0109593
XlogP30.70 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 278.87 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.004000 mmHg @ 25.00 °C. (est)
Flash Point 252.00 °F. TCC ( 122.50 °C. ) (est)
logP (o/w) 0.670
Soluble in water, 2.324e+005 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD25 105 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorypharmaceuticals / chemical synthisis
Recommendation for thionicotinamide usage levels up tonot for fragrance use.
Recommendation for thionicotinamide flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

amino-3-pyridylmethane-1-thione nicotinamide, thio- nicotinothioamide pyridine-3-carbothioamide pyridine-3-carbothioic acid amide pyridine-3-thiocarboxamide 3- pyridinecarbothioamide 3- pyridinethiocarboxamide 3- pyridylthiocarboxamide thio-3-pyridinecarboxamide 3- thioamidopyridine 3- thiocarbamoylpyridine PubMed: Suppression of Cytosolic NADPH Pool by Thionicotinamide Increases Oxidative Stress and Synergizes with Chemotherapy. PubMed: Boronic acid-containing CXCR1/2 antagonists: Optimization of metabolic stability, in vivo evaluation, and a proposed receptor binding model. PubMed: Electrochemistry, surface plasmon resonance, and quartz crystal microbalance: an associative study on cytochrome c adsorption on pyridine tail-group monolayers on gold. PubMed: Spectrophotometric method for the assay of steroid 5α-reductase activity of rat liver and prostate microsomes. 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PubMed: Determinants of substrate specificity for saccharopine dehydrogenase from Saccharomyces cerevisiae. PubMed: Molecular cloning and characterization of a novel lactate dehydrogenase gene from Clonorchis sinensis. PubMed: Electron transfer kinetics and mechanistic study of the thionicotinamide coordinated to the pentacyanoferrate(III)/(II) complexes: a model system for the in vitro activation of thioamides anti-tuberculosis drugs. PubMed: Kinetic study of the enzymatic cycling reaction conducted with 3alpha-hydroxysteroid dehydrogenase in the presence of excessive thio-NAD(+) and NADH. PubMed: Urea transport in MDCK cells that are stably transfected with UT-A1. PubMed: Interactions between transhydrogenase and thio-nicotinamide Analogues of NAD(H) and NADP(H) underline the importance of nucleotide conformational changes in coupling to proton translocation. PubMed: EPYLRFamide-mediated reduction of acetylcholine-induced inward currents in Helix lucorum-identified neurones: role of NAADP-dependent and IP3-dependent Ca2+ release from internal stores, calmodulin and Ca2+/calmodulin-dependent protein kinase II. PubMed: Tartrate dehydrogenase catalyzes the stepwise oxidative decarboxylation of D-malate with both NAD and thio-NAD. PubMed: Structures of D-glyceraldehyde-3-phosphate dehydrogenase complexed with coenzyme analogues. PubMed: The determination of ketone bodies: preanalytical, analytical and physiological considerations. PubMed: Mycobacterium tuberculosis lipoamide dehydrogenase is encoded by Rv0462 and not by the lpdA or lpdB genes. PubMed: Interaction of NADP(H) with oxidized and reduced P450 reductase during catalysis. Studies with nucleotide analogues. PubMed: UT-A urea transporter protein expressed in liver: upregulation by uremia. PubMed: InsP3, but not novel Ca2+ releasers, contributes to agonist-initiated contraction in rabbit airway smooth muscle. PubMed: Thio-NADP is not an antagonist of NAADP. PubMed: Azotobacter vinelandii glucose 6-phosphate dehydrogenase properties of NAD- and NADP-linked reactions. PubMed: Nicotinate-adenine dinucleotide phosphate-induced Ca(2+)-release does not behave as a Ca(2+)-induced Ca(2+)-release system. PubMed: Palmitoyl-CoA potentiates the Ca2+ release elicited by cyclic ADP-ribose. PubMed: Purification and characterization of Azotobacter vinelandii glucose-6-phosphate dehydrogenase: dual coenzyme specificity. PubMed: Nicotinate adenine dinucleotide phosphate (NAADP) triggers a specific calcium release system in sea urchin eggs. PubMed: The urease inhibitor acetohydroxamic acid is transported by the urea pathway in rat terminal IMCD. PubMed: Crystal structures of chicken liver dihydrofolate reductase: binary thioNADP+ and ternary thioNADP+.biopterin complexes. PubMed: Selectivity in the binding of NAD(P)+ analogues to NAD- and NADP-dependent pig heart isocitrate dehydrogenases. A nuclear magnetic resonance study. PubMed: The effect of methimazole on thioamide bioactivation and toxicity. PubMed: Multiple isotope effects with alternative dinucleotide substrates as a probe of the malic enzyme reaction. PubMed: Analogues of NADP(+) as inhibitors and coenzymes for NADP(+) malic enzyme from maize leaves. PubMed: The S-oxidation of thioamides by rat liver microsomes. PubMed: Kinetic mechanism of the endogenous lactate dehydrogenase activity of duck epsilon-crystallin. PubMed: The metabolism of thionicotinamide in the rat. PubMed: Clinical usefulness of malate dehydrogenase and its mitochondrial isoenzyme in comparison with aspartate aminotransferase and its mitochondrial isoenzyme in sera of patients with liver disease. PubMed: In vitro evaluation of nicotinamide riboside analogs against Haemophilus influenzae. PubMed: Distance between the substrate and regulatory reduced coenzyme binding sites of bovine liver glutamate dehydrogenase by resonance energy transfer. PubMed: Regulation of coenzyme utilization by mitochondrial NAD(P)-dependent malic enzyme. PubMed: Assay of creatine kinase in microtiter plates using thio-NAD to allow monitoring at 405 nM. PubMed: ALT reagent with thionicotinamide adenine dinucleotide. PubMed: Isolation, characterization, and biological activity of ferredoxin-NAD+ reductase from the methane oxidizer Methylosinus trichosporium OB3b. PubMed: Substrate specificity of nicotinamide methyltransferase isolated from porcine liver. PubMed: The mechanism of peroxidase-mediated cytotoxicity. II. Role of the heme moiety. PubMed: Inhibitory effects of niacin and its analogues on induction of ornithine decarboxylase activity by diethylnitrosamine in rat liver. PubMed: Distances among coenzyme and metal sites of NADP+-dependent isocitrate dehydrogenase using resonance energy transfer. PubMed: Interactions of nicotinamide-adenine dinucleotide phosphate analogues and fragments with pigeon liver malic enzyme. Synergistic effect between the nicotinamide and adenine moieties. PubMed: [Simultaneous assay of serum lactate dehydrogenase activities depending on NAD (N) and thio-NAD (T), and the clinical significance of N/T values]. PubMed: A one-step enzymatic assay for the measurement of 17 beta-hydroxy- and 17-oxo-steroid profiles in biological samples. PubMed: Simultaneous determination of multiple forms of lactate dehydrogenase based on NAD and thio-NAD. PubMed: Studies on NADH(NADPH)-cytochrome c reductase (FMN-containing) from yeast: steady-state kinetic properties of the flavoenzyme from top-fermenting ale yeast. PubMed: Protonation mechanism and location of rate-determining steps for the Ascaris suum nicotinamide adenine dinucleotide-malic enzyme reaction from isotope effects and pH studies. PubMed: Cytochemical localization of nicotinamide adenine dinucleotide phosphatase (NADPase) in bovine Leydig cells. PubMed: The redox state of activated bleomycin. PubMed: Kinetic and spectroscopic studies of transhydrogenase activity and nucleotide site of lipoamide dehydrogenase. PubMed: Variation of transition-state structure as a function of the nucleotide in reactions catalyzed by dehydrogenases. 2. Formate dehydrogenase. PubMed: Synthesis and properties of (4-13C)NAD+. Observation of its binding to yeast alcohol dehydrogenase by 13C-NMR spectroscopy. PubMed: Bovine lens aldehyde dehydrogenase. Kinetics and mechanism. PubMed: Adenosine diphosphoribose transfer reactions catalyzed by Bungarus fasciatus venom NAD glycohydrolase. PubMed: Use of transferred nuclear Overhauser effect measurements to compare binding of coenzyme analogues to dihydrofolate reductase. PubMed: Oxidation of the 17-aldol (20 beta hydroxy-21-aldehyde) intermediate of corticosteroid metabolism to hydroxy acids by homogeneous human liver aldehyde dehydrogenases. PubMed: Regulation of coenzyme utilization by bovine liver glutamate dehydrogenase: investigations using thionicotinamide analogues of NAD and NADP in a dual wavelength assay. PubMed: Negative cooperativity between folinic acid and coenzyme in their binding to Lactobacillus casei dihydrofolate reductase. PubMed: Effects of coenzyme binding on histidine residues of Lactobacillus casei dihydrofolate reductase. PubMed: Dual nucleotide specificity of bovine glutamate dehydrogenase. The role of negative co-operativity. PubMed: Energy-linked mitochondrial transhydrogenation from NADPH to NADP analogs. PubMed: Effect of pH on the mitochondrial energy-linked and non-energy-linked transhydrogenation reactions. PubMed: Energy-linked transhydrogenation from NADPH to [14C]NADP. PubMed: Phosphorus-31 nuclear magnetic resonance studies of the binding of oxidized coenzymes to Lactobacillus casei dihydrofolate reductase. PubMed: Proton nuclear magnetic resonance saturation transfer studies of coenzyme binding to Lactobacillus casei dihydrofolate reductase. PubMed: Binding of coenzyme analogues to Lactobacillus casei dihydrofolate reductase: binary and ternary complexes. PubMed: Self-inactivation of an erythrocyte NAD glycohydrolase. PubMed: Kinetic studies of multifunctional reactions catalysed by lipoamide dehydrogenase. PubMed: Simultaneous analysis of NAD- and NADP-linked activities of dual nucleotide-specific dehydrogenases. Application to Leuconostoc mesenteroides glucose-6-phosphate dehydrogenase. PubMed: Mercury complexes of thionicotinamide adenine dinucleotide. PubMed: Fluorescence properties of reduced thionicotinamide--adenine dinucleotide and of its complex with octopine dehydrogenase. PubMed: Circular dichroic properties and conformation of thionicotinamide dinucleotides bound to horse-liver alcohol dehydrogenase. PubMed: Circular dichroic properties and conformation of thionicotinamide dinucleotides. PubMed: Further studies on the properties of glucose 6-phosphate dehydrogenase from the coccidium Eimeria stiedai (Protozoa). PubMed: Fluorescence energy transfer between heterologous active sites of affinity-labeled aspartokinase of Escherichia coli. PubMed: Application of nicotin amide-adenine dinucleotide analogs for clinical enzymology: alcohol dehydrogenase activity in liver injury. PubMed: Application of nicotinamide-adenine dinucleotide analogs for clinical enzymology: a spectrophotometric method for clinical analysis of lactate dehydrogenase patterns with the use of a nicotinamide-adenine dinucleotide analog. PubMed: Demonstration and possible function of NADH:NAD+ transhydrogenase from ascaris muscle mitochondria. PubMed: Human liver akdehyde dehydrogenase. Kinetics of aldehyde oxidation. PubMed: Treatment of psoriasis with 6-aminonicotinamide. PubMed: Separation behaviour of nicotinamide and thionicotinamide derivatives on Dowex 1-X8. PubMed: Covalent binding of 3-pyridinealdehyde nicotinamide adenine dinucleotide and substrate to glyceraldehyde 3-phosphate dehydrogenase. PubMed: 3Alpha-hydroxysteroid dehydrogenase from Pseudomonas testosteroni: kinetic properties with NAD and its thionicotinamide analogue. PubMed: Thionicotinamide-NADP, a nucleotide analog interfering with ferredoxin-NADP reductase-ferredoxin interaction. PubMed: Carbohydrate metabolism during morphogenesis of Coprinus lagopus (sensu Buller). PubMed: [Pharmacologic and biochemical properties of thionicotinamide (thio-NA) and its NAD (P)-analogues]. PubMed: CO(2) Metabolism in Corn Roots. II. Intracellular Distribution of Enzymes. PubMed: Nicotinamide-adenine dinucleotide pyrophosphatase in the growing and aging mosquito. PubMed: Comparative aspects of some bacterial dehydrogenases and transhydrogenases. PubMed: THE THIONICOTINAMIDE ANALOGS OF DPN AND TPN. II. ENZYME STUDIES. PubMed: THE THIONICOTINAMIDE ANALOGS OF DPN AND TPN. I. PREPARATION AND ANALYSIS. PubMed: Coenzyme analogs. II. Photochemical inactivation of reducd thionicotinamide adenine dinucleotide. PubMed: Coenzyme analogs. I. Preparation and properties of thionicotinamide methiodide.