Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H6N2O |
Molecular Weight | 122.1246 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CC=NC=C1
InChI
InChIKey=VFQXVTODMYMSMJ-UHFFFAOYSA-N
InChI=1S/C6H6N2O/c7-6(9)5-1-3-8-4-2-5/h1-4H,(H2,7,9)
Molecular Formula | C6H6N2O |
Molecular Weight | 122.1246 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Isonicotinamide is the amide form of isonicotinic acid. It is often used as a scaffold for other synthetic compounds. Isonicotinamide has been identified as inducing apoptosis through DNA fragmentation in leukemia cell models and has been studied in mice or the prevention of diabetes. Isonicotinamide activates the NAD-dependent histone deacetylase SIR2 by raising intracellular NAD+ concentration.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006309 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9972261 |
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Target ID: P06700 Gene ID: 851520.0 Gene Symbol: SIR2 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22539348 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Apoptosis induced by niacin-related compounds in HL-60 cells. | 1998 Dec |
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New polymorphs of isonicotinamide and nicotinamide. | 2011 Feb 7 |
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Antinociceptive and anti-inflammatory activities of nicotinamide and its isomers in different experimental models. | 2011 Oct |
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Protective effects of a nicotinamide derivative, isonicotinamide, against streptozotocin-induced β-cell damage and diabetes in mice. | 2013 Dec 6 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24246675
Curator's Comment: referenced study was conducted in mouse
Male C57BL/6 mice were induced to diabetes by giving one of three doses of streptozotocin (STZ; 65, 75, 100 mg/kg BW) alone or in combination with subsequent high-fat diet. Mice were treated with a daily intraperitoneal dose of 250 mg/kg BW isoncotinamide. Isonicotinamide effectively prevented hyperglycemia induced by high doses of STZ (75 and 100 mg/kg BW) alone, and also low-dose (65 mg/kg BW) in combination with a high-fat diet. The protective effects were associated with decreased apoptosis of beta-cells.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9972261
Human myeloid leukemia (HL-60) cells were cultured in RPMI 1640 medium with 100 U/mL penicillin, 100 microgram/mL streptomycin, 2 mM L-glutamine, and 10% heat-inactivated fetal bovine serum at 37 deg-C in a 5% CO2 atmosphere. Cells were treated with 1 - 10 mM isonicotinamide. Apoptosis was monitored by flow cytometry. Isonicotinamide had a strong effect of inducing DNA fragmentation leading to apoptosis.
Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 01:04:46 GMT 2023
by
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on
Sat Dec 16 01:04:46 GMT 2023
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Record UNII |
4H3BH6YX9Q
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Record Status |
Validated (UNII)
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Record Version |
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ISONICOTINAMIDE
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