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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
Structure of ISONIACINAMIDE

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)

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P06700
Gene ID: 851520.0
Gene Symbol: SIR2
Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Apoptosis induced by niacin-related compounds in HL-60 cells.
1998 Dec
New polymorphs of isonicotinamide and nicotinamide.
2011 Feb 7
Antinociceptive and anti-inflammatory activities of nicotinamide and its isomers in different experimental models.
2011 Oct
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
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
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
by admin
on Sat Dec 16 01:04:46 GMT 2023
Edited
by admin
on Sat Dec 16 01:04:46 GMT 2023
Record UNII
4H3BH6YX9Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISONIACINAMIDE
INCI  
INCI  
Official Name English
ISONIAZID IMPURITY B [EP IMPURITY]
Common Name English
ISONIACINAMIDE [INCI]
Common Name English
ISONICOTINAMIDE
Systematic Name English
4-CARBAMOYLPYRIDINE
Systematic Name English
PYRIDINE-4-CARBOXAMIDE
Systematic Name English
ISONICOTINIC ACID AMIDE
Systematic Name English
4-(AMINOCARBONYL)PYRIDINE
Systematic Name English
NSC-82353
Code English
4-PYRIDINECARBOXAMIDE
Systematic Name English
4-PICOLINAMIDE
Systematic Name English
Code System Code Type Description
PUBCHEM
15074
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
FDA UNII
4H3BH6YX9Q
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
DAILYMED
4H3BH6YX9Q
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
MESH
C027681
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
CHEBI
6031
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
NSC
82353
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID3020756
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
215-926-2
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
RXCUI
1312616
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY RxNorm
CAS
1453-82-3
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
WIKIPEDIA
ISONICOTINAMIDE
Created by admin on Sat Dec 16 01:04:46 GMT 2023 , Edited by admin on Sat Dec 16 01:04:46 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY