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Details

Stereochemistry ACHIRAL
Molecular Formula C16H13N3O4
Molecular Weight 311.2921
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITRAQUAZONE

SMILES

CCN1C(=O)N(C2=CC(=CC=C2)[N+]([O-])=O)C3=C(C=CC=C3)C1=O

InChI

InChIKey=GNWCRBFQZDJFTI-UHFFFAOYSA-N
InChI=1S/C16H13N3O4/c1-2-17-15(20)13-8-3-4-9-14(13)18(16(17)21)11-6-5-7-12(10-11)19(22)23/h3-10H,2H2,1H3

HIDE SMILES / InChI

Molecular Formula C16H13N3O4
Molecular Weight 311.2921
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Nitraquazone (TVX 2706) is an phosphodiesterase inhibitor with antiinflammatory action. It strongly enhances the increase in intracellular levels of cyclic AMP caused by appropriate effectors in all systems tested so far. EC50 values are in the submicromolar range. The effect is apparently neither due to an increased responsiveness of the hybrid cells for an effector like prostaglandin E1 nor to an increased activity of adenylate cyclase, but to an inhibition of both low and high affinity cyclic AMP phosphodiesterases. Half-maximal inhibition of enzyme activity is obtained at 10 uM TVX 2706. TVX 2706 does not interfere with the calmodulin activation of phosphodiesterase. Nitraquazone affected cytokine production by PHA-stimulated human blood cells. Nitraquazone was active in reducing the production of IL-5 (IC50 = 0.8 uM), while its potency against IL-2, GM-CSF and IFN-gamma was 3-6 times lower.

Approval Year

PubMed

PubMed

TitleDatePubMed
Modulation of TNF alpha and IL-1 beta from endotoxin-stimulated monocytes by selective PDE isozyme inhibitors.
1993
Characterization of phosphodiesterase 4 in guinea-pig macrophages: multiple activities, association states and sensitivity to selective inhibitors.
1998 May
Phosphodiesterase 4 inhibitors, structurally unrelated to rolipram, as promising agents for the treatment of asthma and other pathologies.
2000 May
Patents

Patents

Sample Use Guides

In Vitro Use Guide
Curator's Comment: The cyclic AMP phosphodiesterases (PDE) in guinea-pig peritoneal macrophages were isolated, partially characterized and their role in regulating the cyclic AMP content in intact cells evaluated. Approximately 90% of the PDE activity was membrane-bound and exclusively hydrolyzed cyclic AMP. This activity was not removed by KCl (200 mM) but was readily solubilized by the non-ionic detergent, Triton X-100 (1% v/v).
Greater than 80% of the hydrolytic activity was suppressed by the PDE4 inhibitor nitraquazone with IC50 of 540 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:24:27 GMT 2023
Edited
by admin
on Fri Dec 15 16:24:27 GMT 2023
Record UNII
1YF1KXP4QF
Record Status Validated (UNII)
Record Version
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Name Type Language
NITRAQUAZONE
INN  
INN  
Official Name English
3-ETHYL-1-(M-NITROPHENYL)-2,4(1H,3H)-QUINAZOLINEDIONE
Systematic Name English
nitraquazone [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
Code System Code Type Description
EVMPD
SUB09317MIG
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
MESH
C044248
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
INN
5727
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
SMS_ID
100000084119
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
PUBCHEM
68765
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
NCI_THESAURUS
C73098
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL88990
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
CAS
56739-21-0
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID00972177
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
FDA UNII
1YF1KXP4QF
Created by admin on Fri Dec 15 16:24:27 GMT 2023 , Edited by admin on Fri Dec 15 16:24:27 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY