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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/22335564 | https://www.ncbi.nlm.nih.gov/pubmed/24405692 | http://ir.nivalis.com/press-releases/detail/12/n30-pharmaceuticals-announces-first-patient-treated-in

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
5 mg 1 times / day multiple, intravenous
Studied dose
Dose: 5 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg, 1 times / day
Sources: Page: p.326
unhealthy, 32.9
n = 14
Health Status: unhealthy
Condition: Asthma
Age Group: 32.9
Sex: M+F
Population Size: 14
Sources: Page: p.326
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery of s-nitrosoglutathione reductase inhibitors: potential agents for the treatment of asthma and other inflammatory diseases.
2011 May 12
A nonclinical safety and pharmacokinetic evaluation of N6022: a first-in-class S-nitrosoglutathione reductase inhibitor for the treatment of asthma.
2012 Feb
Mechanism of inhibition for N6022, a first-in-class drug targeting S-nitrosoglutathione reductase.
2012 Mar 13
Pharmacologic inhibition of S-nitrosoglutathione reductase protects against experimental asthma in BALB/c mice through attenuation of both bronchoconstriction and inflammation.
2014 Jan 10
Patents

Sample Use Guides

A 5 mg single dose given intravenously via syringe pump over 1 minute.
Route of Administration: Intravenous
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
Created
by admin
on Sat Dec 16 01:25:09 GMT 2023
Edited
by admin
on Sat Dec 16 01:25:09 GMT 2023
Record UNII
80LIU5P95D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N-6022
Common Name English
3-(5-(4-(1H-IMIDAZOL-1-YL)PHENYL)-1-(4-CARBAMOYL-2-METHYLPHENYL)-1H-PYRROL-2-YL)PROPANOIC ACID
Systematic Name English
N6022
Code English
Code System Code Type Description
FDA UNII
80LIU5P95D
Created by admin on Sat Dec 16 01:25:09 GMT 2023 , Edited by admin on Sat Dec 16 01:25:09 GMT 2023
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PUBCHEM
44623946
Created by admin on Sat Dec 16 01:25:09 GMT 2023 , Edited by admin on Sat Dec 16 01:25:09 GMT 2023
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DRUG BANK
DB12206
Created by admin on Sat Dec 16 01:25:09 GMT 2023 , Edited by admin on Sat Dec 16 01:25:09 GMT 2023
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CAS
1208315-24-5
Created by admin on Sat Dec 16 01:25:09 GMT 2023 , Edited by admin on Sat Dec 16 01:25:09 GMT 2023
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EPA CompTox
DTXSID801025710
Created by admin on Sat Dec 16 01:25:09 GMT 2023 , Edited by admin on Sat Dec 16 01:25:09 GMT 2023
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