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Details

Stereochemistry ACHIRAL
Molecular Formula C24H22N4O3
Molecular Weight 414.4565
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N-6022

SMILES

CC1=C(C=CC(=C1)C(N)=O)N2C(CCC(O)=O)=CC=C2C3=CC=C(C=C3)N4C=CN=C4

InChI

InChIKey=YVPGZQLRPAGKLA-UHFFFAOYSA-N
InChI=1S/C24H22N4O3/c1-16-14-18(24(25)31)4-9-21(16)28-20(8-11-23(29)30)7-10-22(28)17-2-5-19(6-3-17)27-13-12-26-15-27/h2-7,9-10,12-15H,8,11H2,1H3,(H2,25,31)(H,29,30)

HIDE SMILES / InChI

Molecular Formula C24H22N4O3
Molecular Weight 414.4565
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

N6022 is a novel, first-in-class drug with potent reversible inhibitory activity against S-nitrosoglutathione reductase (GSNOR) and a potential agent for the treatment of acute asthma and cystic fibrosis (CF). Decreased levels of GSNO in the lungs of asthmatics and cystic fibrosis patients have been attributed to increased GSNO catabolism via GSNO reductase (GSNOR) leading to loss of GSNO- and NO- mediated bronchodilatory and anti-inflammatory actions. N6022 restore GSNO levels by inhibiting GSNOR. Inhibition of GSNOR by N6022 has shown safety and efficacy in animal models of asthma, chronic obstructive pulmonary disease, and inflammatory bowel disease. N6022 reduced bronchoconstriction and pulmonary inflammation in a mouse model of asthma. The significant bronchodilatory and anti-inflammatory actions of N6022 in the airways are consistent with restoration of GSNO levels through GSNOR inhibition.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.5 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
A 5 mg single dose given intravenously via syringe pump over 1 minute.
Route of Administration: Intravenous
In Vitro Use Guide
N6022 and selected compounds were screened for cytotoxicity toward A549 epithelial lung cells. Minimal cytotoxicity (IC50's > 100 uM) was observed using this assay.
Substance Class Chemical
Record UNII
80LIU5P95D
Record Status Validated (UNII)
Record Version