Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H7N3O |
| Molecular Weight | 137.1393 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CN=C(N)C=C1
InChI
InChIKey=ZLWYEPMDOUQDBW-UHFFFAOYSA-N
InChI=1S/C6H7N3O/c7-5-2-1-4(3-9-5)6(8)10/h1-3H,(H2,7,9)(H2,8,10)
| Molecular Formula | C6H7N3O |
| Molecular Weight | 137.1393 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
6-Aminonicotinamide is an inhibitor of the NADP+-dependent enzyme, 6-phosphogluconate dehydrogenase; it also interferes with glycolysis, resulting in ATP depletion. It was shown, that the combination of 6-aminonicotinamide with 2-deoxy-D-glucose induces cell cycle arrest and apoptosis selectively in irradiated human malignant cells.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Major effects on teratogen-induced facial clefting in mice determined by a single genetic region. | 1990 Sep |
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| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
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| Energy metabolism and cerebral blood flow during cytotoxic brain edema induced by 6-aminonicotinamide. | 2003 |
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| Contribution of oxidative stress to radiosensitization by a combination of 2-DG and 6-AN in human cancer cell line. | 2003 Dec |
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| A functional observational battery for use in canine toxicity studies: development and validation. | 2003 Nov-Dec |
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| Inhibition of the pentose phosphate pathway decreases ischemia-reperfusion-induced creatine kinase release in the heart. | 2004 Apr 1 |
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| Discriminative power of an assay for automated in vitro screening of teratogens. | 2004 Aug |
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| Radiosensitization of murine Ehrlich ascites tumor by a combination of 2-deoxy-D-glucose and 6-aminonicotinamide. | 2004 Dec |
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| Metallothionein prevents neurodegeneration and central nervous system cell death after treatment with gliotoxin 6-aminonicotinamide. | 2004 Jul 1 |
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| Effects of oxidative stress and inhibitors of the pentose phosphate pathway on sexually dimorphic production of IFN-tau by bovine blastocysts. | 2004 May |
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| Comparative sensitivity of Xenopus tropicalis and Xenopus laevis as test species for the FETAX model. | 2004 Nov-Dec |
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| Involvement of the pentose phosphate pathway and redox regulation in fertilization in the mouse. | 2005 Apr |
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| Cytosolic NADPH may regulate differences in basal Nox oxidase-derived superoxide generation in bovine coronary and pulmonary arteries. | 2005 Jan |
|
| Correlation of susceptibility to 6-aminonicotinamide and hydrocortisone-induced cleft palate. | 2005 Mar 18 |
|
| Radiosensitization by 6-aminonicotinamide and 2-deoxy-D-glucose in human cancer cells. | 2005 May |
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| Fetal hydrocephalus, intrauterine diagnosis and therapy considerations: an experimental rat model. | 2005 May |
|
| Effects of D-glucose concentration, D-fructose, and inhibitors of enzymes of the pentose phosphate pathway on the development and sex ratio of bovine blastocysts. | 2005 Oct |
|
| Effects of small molecules on chaperone-mediated autophagy. | 2005 Oct-Dec |
|
| Metallothionein mediates leukocyte chemotaxis. | 2005 Sep 15 |
|
| Role of pentose phosphate pathway-derived NADPH in hypoxic pulmonary vasoconstriction. | 2006 |
|
| Glucose-6-phosphate dehydrogenase-derived NADPH fuels superoxide production in the failing heart. | 2006 Aug |
|
| Hypoxia promotes relaxation of bovine coronary arteries through lowering cytosolic NADPH. | 2006 Jun |
|
| Thiol oxidation inhibits nitric oxide-mediated pulmonary artery relaxation and guanylate cyclase stimulation. | 2006 Mar |
|
| Metallothionein I + II expression and roles during neuropathology in the CNS. | 2006 May |
|
| Protection by 6-aminonicotinamide against oxidative stress in cardiac cells. | 2006 Oct |
|
| Upregulation of glucose-6-phosphate dehydrogenase and NAD(P)H oxidase activity increases oxidative stress in failing human heart. | 2007 Aug |
|
| The Balance between Life and Death of Cells: Roles of Metallothioneins. | 2007 Feb 7 |
|
| The effect of glucose on the progression of the nuclear maturation of pig oocytes. | 2007 Jun |
|
| The role of multiple drug resistance proteins in fetal and/or placental protection against teratogen-induced orofacial clefting. | 2007 Nov |
|
| Pro-inflammatory cytokines increase reactive oxygen species through mitochondria and NADPH oxidase in cultured RPE cells. | 2007 Oct |
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| The discovery of 6-amino nicotinamides as potent and selective histone deacetylase inhibitors. | 2007 Oct 1 |
|
| Oxidative pentose phosphate pathway-dependent sugar sensing as a mechanism for regulation of root ion transporters by photosynthesis. | 2008 Apr |
|
| Automated analysis of contractility in the embryonic stem cell test, a novel approach to assess embryotoxicity. | 2008 Dec |
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| Confirmation of the role of N-acetyltransferase 2 in teratogen-induced cleft palate using transgenics and knockouts. | 2008 Jun |
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| 1-Methylnicotinamide and nicotinamide: two related anti-inflammatory agents that differentially affect the functions of activated macrophages. | 2008 Mar-Apr |
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| Evaluation of the embryotoxic potency of compounds in a newly revised high throughput embryonic stem cell test. | 2008 Oct |
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| Altering chemosensitivity by modulating translation elongation. | 2009 |
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| Synergistic activation of glucose-6-phosphate dehydrogenase and NAD(P)H oxidase by Src kinase elevates superoxide in type 2 diabetic, Zucker fa/fa, rat liver. | 2009 Aug 1 |
|
| A new strategy to improve the efficiency and sustainability of Candida parapsilosis catalyzing deracemization of (R,S)-1-phenyl-1,2-ethanediol under non-growing conditions: increase of NADPH availability. | 2009 Jan |
|
| Reactive oxygen species-independent oxidation of thioredoxin in hypoxia: inactivation of ribonucleotide reductase and redox-mediated checkpoint control. | 2009 Jun 19 |
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| Glucose regulated protein 78 prompts scavenger receptor A-mediated secretion of tumor necrosis factor-α by RAW 264.7 cells. | 2009 Sep |
|
| Disentangling cellular proliferation and differentiation in the embryonic stem cell test, and its impact on the experimental protocol. | 2009 Sep |
|
| Delineating biological pathways unique to embryonic stem cell-derived insulin-producing cell lines from their noninsulin-producing progenitor cell lines. | 2010 Aug |
|
| Teratogen-induced oxidative stress targets glyceraldehyde-3-phosphate dehydrogenase in the organogenesis stage mouse embryo. | 2010 Dec |
|
| DCB-3503, a tylophorine analog, inhibits protein synthesis through a novel mechanism. | 2010 Jul 15 |
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| Glucose is necessary for stabilization of hypoxia-inducible factor-1alpha under hypoxia: contribution of the pentose phosphate pathway to this stabilization. | 2010 Jul 16 |
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| Transcriptomics-based identification of developmental toxicants through their interference with cardiomyocyte differentiation of embryonic stem cells. | 2010 Mar 15 |
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| Genes, environment, and orofacial clefting: N-acetyltransferase and folic acid. | 2010 Sep |
|
| Metabolic oxidative stress induced by a combination of 2-DG and 6-AN enhances radiation damage selectively in malignant cells via non-coordinated expression of antioxidant enzymes. | 2010 Sep 28 |
|
| A high-throughput screen for teratogens using human pluripotent stem cells. | 2014 Jan |
Sample Use Guides
in rats: 6-aminonicotinamide was administered by i.p. injection 5 days after right optic nerve crush in doses of either 5 or 10 mg/kg body weight. High doses of 6-aminonicotinamide resulted in loss of astrocytes and intracellular glial edema in both crushed and unoperated optic nerve.
Route of Administration:
Intraperitoneal
Combination (5 mM 2-deoxy-D-glucose (2-DG) + 5 uM 6-aminonicotinamide (6-AN) +2 Gy (radiation dose)) treatment result in significant cell growth inhibition and induced ROS generation in all cancer cells studied. Human tumor cell lines of various origins viz A549 (lung carcinoma), U-87 (glioblastoma), OCT-1 (from human oral carcinoma), 4197 (squamous cell carcinoma), and a non- malignant cell line: MRC-5 (human fibroblasts) were used for the experiments. The results revealed that combination (2-DG+6-AN+2 Gy) treatment result in significant cell growth inhibition and induced ROS generation in all cancer cells studied. The anti-proliferative effect was related to the ability of combination (2-DG+6-AN+2 Gy) to provoke growth inhibition at the G2/M arrest and apoptosis. Furthermore, combination (2-DG+6-AN+2 Gy) induced G2/M arrest is closely correlated to decreased cyclin A, cyclin B1, and cdc2 levels.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:10:42 GMT 2023
by
admin
on
Fri Dec 15 15:10:42 GMT 2023
|
| Record UNII |
D6FNW67F2B
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| Record Status |
Validated (UNII)
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| Record Version |
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21206
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9500
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C38127
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206-349-7
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D015120
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D6FNW67F2B
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74514
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329-89-5
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DTXSID5051446
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