N-6022

Investigational

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 Search

SMILES

CC1=CC(=CC=C1N2C(CCC(O)=O)=CC=C2C3=CC=C(C=C3)N4C=CN=C4)C(N)=O

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900320
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
alcohol dehydrogenase 5 (class III), chi polypeptide 1 Target ID: 1.05067888E8 Gene Symbol: ADH5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22335564	Inhibitor 8504		2.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 Sources: https://clinicaltrials.gov/ct2/show/NCT01316315	Primary		Phase II 1147	Unknown Approved Use Unknown
Cystic fibrosis 120 Sources: https://clinicaltrials.gov/ct2/show/NCT01746784	Primary		Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
465 ng/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1270 ng/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1400 ng/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
287 ng/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	5 mg 1 times / day steady-state, intravenous dose: 5 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1110 ng/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	10 mg 1 times / day steady-state, intravenous dose: 10 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2320 ng/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	20 mg 1 times / day steady-state, intravenous dose: 20 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
138 ng × h/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
334 ng × h/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
669 ng × h/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
149 ng × h/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	5 mg 1 times / day steady-state, intravenous dose: 5 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
367 ng × h/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	10 mg 1 times / day steady-state, intravenous dose: 10 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
811 ng × h/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT01339897?tab=results	20 mg 1 times / day steady-state, intravenous dose: 20 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	N6022 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/29642282	unhealthy, 32.9 Health Status: unhealthy Age Group: 32.9 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/29642282	Sources: https://pubmed.ncbi.nlm.nih.gov/29642282

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P008TZ4	https://www.1pchem.com/search?query=1P008TZ4
AChemBlock	M15768	http://www.achemblock.com/catalogsearch/result/?q=M15768
AK Scientific	2573AH	https://aksci.com/item_detail.php?cat=2573AH
ApexBio Technology	B1111	https://www.apexbt.com/catalogsearch/result/?q=B1111
AstaTech	40928	http://astatechinc.com/CPSResult.php?CRNO=40928
Axon MedChem	1822	https://www.axonmedchem.com/product/1822
BLD Pharm	BD629997	http://www.bldpharm.com/search/Search.html?keyword=BD629997
Cayman Chemical	21269	http://www.caymanchem.com/app/template/Product.vm/catalog/21269
Chem Scene	CS-2034	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2034
ChemShuttle	180945	https://www.chemshuttle.com/catalogsearch/result/?q=180945
Debye Scientific	DA-47186	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-47186
eMolecules	42777451	https://orderbb.emolecules.com/search/#?query=42777451
eNovation Chemicals	D388310	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D388310&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A343	http://www.excenen.com/searchresultlist.php?id=EX-A343
mcule	MCULE-4036800297	https://mcule.com/MCULE-4036800297/
MedChem Express	HY-14984	https://www.medchemexpress.com/search.html?q=HY-14984&ft=&fa=&fp=
Molnova	M10777	https://www.molnova.com/en/serch-list.html?keywords=M10777
MolPort	MolPort-035-789-691	https://www.molport.com/shop/molecule-link/MolPort-035-789-691
Selleck Chemicals	S7589	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7589
ShangHai Biochempartner	BCP001105	http://www.biochempartner.com/search_BCP001105
ShangHai Biochempartner	BCP09367	http://www.biochempartner.com/search_BCP09367
TargetMol	T6901	https://www.targetmol.com/search?keyword=T6901

PubMed

Title	Date	PubMed
Pharmacologic inhibition of S-nitrosoglutathione reductase protects against experimental asthma in BALB/c mice through attenuation of both bronchoconstriction and inflammation.	2014-01-10	24405692
Mechanism of inhibition for N6022, a first-in-class drug targeting S-nitrosoglutathione reductase.	2012-03-13	22335564
A nonclinical safety and pharmacokinetic evaluation of N6022: a first-in-class S-nitrosoglutathione reductase inhibitor for the treatment of asthma.	2012-02	22210450
Discovery of s-nitrosoglutathione reductase inhibitors: potential agents for the treatment of asthma and other inflammatory diseases.	2011-05-12	24900320

Patents

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 Created by `admin` on `Mon Mar 31 20:49:44 GMT 2025` Edited by `admin` on `Mon Mar 31 20:49:44 GMT 2025`
Record UNII	80LIU5P95D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N-6022

Common Name

English

N6022

Preferred Name

English

3-(5-(4-(1H-IMIDAZOL-1-YL)PHENYL)-1-(4-CARBAMOYL-2-METHYLPHENYL)-1H-PYRROL-2-YL)PROPANOIC ACID

Systematic Name

English

Code System Code Type Description

FDA UNII

80LIU5P95D