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Details

Stereochemistry ACHIRAL
Molecular Formula C7H5N3O2
Molecular Weight 163.1335
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7-NITROINDAZOLE

SMILES

[O-][N+](=O)C1=CC=CC2=C1NN=C2

InChI

InChIKey=PQCAUHUKTBHUSA-UHFFFAOYSA-N
InChI=1S/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9)

HIDE SMILES / InChI
7-Nitroindazole (aka 7-NI) is an experimental small molecule that acts as a selective inhibitor of neuronal nitric oxide synthase, which normally converts arginine to citrulline and nitric oxide (NO) in neuronal tissues. It has been investigated for potential use as an anti-nociceptive compound and as a means of mitigating neurodegenerative damage.

CNS Activity

Curator's Comment: referenced study was conducted in mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P29475
Gene ID: 4842.0
Gene Symbol: NOS1
Target Organism: Homo sapiens (Human)
0.9 µM [IC50]
Target ID: P29474|||Q14434
Gene ID: 4846.0
Gene Symbol: NOS3
Target Organism: Homo sapiens (Human)
3.67 null [pEC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Nitric oxide- and oxygen-derived free radical generation from control and lipopolysaccharide-treated rat polymorphonuclear leukocyte.
2001
Protective effect of 7-nitroindazole against DSP-4 induced noradrenaline depletion in mouse hippocampus.
2001
Nitric oxide modulates evoked catecholamine release from canine adrenal medulla.
2001
Comparison of N2O- and chlordiazepoxide-induced behaviors in the light/dark exploration test.
2001 Apr
Prolonged suppression of brain nitric oxide synthase activity by 7-nitroindazole protects against cerebral hypoxic-ischemic injury in neonatal rat.
2001 Aug
Role of nitric oxide in thermoregulation and hypoxic ventilatory response in obese Zucker rats.
2001 Aug 1
Inhibition of neuronal nitric oxide synthase enhances cell proliferation in the dentate gyrus of the adrenalectomized rat.
2001 Aug 17
Nitric oxide enhances MPP(+) inhibition of complex I.
2001 Aug 24
Effects of long-term inhibition of neuronal nitric oxide synthase on blood pressure and renin release.
2001 Dec
Inhibition of different types of nitric oxide synthase: effect on thermoregulation in the rat exposed to high ambient temperature.
2001 Dec 4
Effects of L-arginine on penicillin-induced epileptiform activity in rats.
2001 Jul
7-Nitroindazole, but not aminoguanidine, attenuates the acute inflammatory responses and brain injury during the early phase of Escherichia coli meningitis in the newborn piglet.
2001 Jul
Contribution of endothelial nitric oxide synthase in the blunted renal responses to volume expansion in diabetic rats.
2001 Jul
Relatively selective neuronal nitric oxide synthase inhibition by 7-nitroindazole in monkey isolated cerebral arteries.
2001 Jul 6
Effect of cyclooxygenase and NO synthase inhibitors on antinociceptive action of acetaminophen.
2001 Jul-Aug
Methamphetamine-induced dopaminergic neurotoxicity: role of peroxynitrite and neuroprotective role of antioxidants and peroxynitrite decomposition catalysts.
2001 Jun
The effects of nitric oxide synthase inhibitors on the sedative effect of clonidine.
2001 Nov
Nitric oxide modulates sympathoexcitatory cardiac-cardiovascular reflexes elicited by bradykinin.
2001 Nov
Role of neuronal nitric oxide synthase in mediating renal hemodynamic changes during pregnancy.
2001 Nov
N(G)-nitro-L-arginine and its methyl ester inhibit brain synthesis of kynurenic acid possibly via nitric oxide-independent mechanism.
2001 Nov-Dec
Nitric oxide inhibition of cAMP synthesis in parotid acini: regulation of type 5/6 adenylyl cyclase.
2001 Oct
Different effects between 7-nitroindazole and L-NAME on cerebral hemodynamics and hippocampal lesions during kainic acid-induced seizures in newborn rabbits.
2001 Oct
Nitric oxide synthase in spinal cord central sensitization following intradermal injection of capsaicin.
2001 Oct
Nitric oxide synthase and cGMP-mediated stimulation of renin secretion.
2001 Oct
Delayed induction of p38 MAPKs in reactive astrocytes in the brain of mice after KA-induced seizure.
2001 Oct 19
Inhibition of nitric oxide production during global ischemia ameliorates ischemic damage of pyramidal neurons in the hippocampus.
2001 Sep
Neuronal nitric oxide synthase (NOS) regulates leukocyte-endothelial cell interactions in endothelial NOS deficient mice.
2001 Sep
Inhibition of neuronal nitric oxide synthase ameliorates renal hyperfiltration in streptozotocin-induced diabetic rat.
2001 Sep
Interactions between nitric oxide and renal nerves in the excretion of a saline load in obese Zucker rats.
2001 Sep
Nitric oxide from perivascular nerves modulates cerebral arterial pH reactivity.
2001 Sep
Delayed induction of alpha B-crystallin in activated glia cells of hippocampus in kainic acid-treated mouse brain.
2001 Sep 1
The nNOS/cGMP signal transducing system is involved in the cardiovascular responses induced by activation of NMDA receptors in the rostral ventrolateral medulla of cats.
2001 Sep 14
Nitric oxide is required for the induction and heterosynaptic spread of long-term potentiation in rat cerebellar slices.
2001 Sep 15
Neuroprotective MK801 is associated with nitric oxide synthase during hypoxia/reoxygenation in rat cortical cell cultures.
2002
Protection of methylmercury effects on the in vivo dopamine release by NMDA receptor antagonists and nitric oxide synthase inhibitors.
2002 Apr
Motor effects of acute and chronic inhibition of nitric oxide synthesis in mice.
2002 Apr
Inhibition of neuronal nitric oxide synthase increases adrenalectomy-induced granule cell death in the rat dentate gyrus.
2002 Apr 12
NO synthase inhibitors attenuate locus coeruleus catecholamine metabolism and behavior induced by morphine withdrawal.
2002 Apr 16
Mechanisms of glutamate release in the rat spinal cord slices during metabolic inhibition.
2002 Feb
Mechanism by which superoxide potentiates tubuloglomerular feedback.
2002 Feb
Neuronal NOS-dependent dilation to flow in coronary arteries of male eNOS-KO mice.
2002 Feb
Involvement of neuronal nitric oxide synthase in restraint stress-induced fever in rats.
2002 Feb 1-15
Multiple mechanisms of vascular smooth muscle relaxation by the activation of proteinase-activated receptor 2 in mouse mesenteric arterioles.
2002 Jan
The effect of 7-nitroindazole on the acquisition and expression of D-methamphetamine-induced place preference in rats.
2002 Jan 25
Alterations of the nitric oxide pathway in cerebral arteries from spontaneously hypertensive rats.
2002 Mar
Endothelin-A receptors and NO mediate decrease in arterial pressure during recovery from restraint.
2002 Mar
Nitric oxide modulation of neurally induced proximal tubular fluid reabsorption in the rat.
2002 Mar 1
Selective inhibition of neuronal nitric oxide synthesis reduces hyperactivity and increases non-selective attention in the Naples High-Excitability rat.
2002 Mar 10
Differential contributions of nitric oxide synthase isoforms at hippocampal formation to negative feedback regulation of penile erection in the rat.
2002 May
Facilitatory role of NO in neural norepinephrine release in the rat kidney.
2002 May
Patents

Sample Use Guides

7-Nitroindazole was administered to mice by intraperitoneal injection in a dose range of 10 - 50 mg/kg. 7-Nitroindazole demonstrated anti-nociceptive effects in the late phase of the formalin-induced hind-paw licking and acetic acid-induced abdominal constriction assays; the ED50 for each assay was 27.5 and 22.5 mg/kg respectively. Maximum antinociceptive activity and NOS inhibition were detected 18-30 min following i.p. administration.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Rabbit aortic rings (with and without endothelium) were mounted for isometric tensile recording in an organ bath containing Krebs solution at 37 deg-C in an atmosphere of 5% CO2. The tissue was placed under an initial tension of 2 g and left to equilibrate for 30 - 45 minutes. Aortic rings were then precontracted with 0.2 micro-M phenylephrine. Once stable contractions were observed, cumulative concentration-effect curves were determined for 7-Nitroindazole (1 micro-M to 1 mM). Concentration-effect curves to 7-Nitroindazole were also determined in rabbit aorta after incubation with the nitric oxide synthase inhibitor L-N^G-nitro arginine p-nitroanilide (50 micro-M) for 60 minutes. The failure of acetylcholine (2 micro-M) to induce relaxation in rabbit aorta was taken as an indication of the absence of a functional endothelium. 7-Nitroindazole caused concentration-dependent relaxations in rabbit aorta with a -log EC50 of 3.67. The relaxant response to 7-Nitroindazole was not significantly different in aortic rings with or without a functional endothelium, or after pretreatment with L-N^G-nitro arginine p-nitroanilide.
Name Type Language
7-NITROINDAZOLE
Systematic Name English
NSC-72843
Code English
NITROINDAZOLE, 7-
Systematic Name English
Code System Code Type Description
PUBCHEM
1893
Created by admin on Fri Dec 15 17:58:30 GMT 2023 , Edited by admin on Fri Dec 15 17:58:30 GMT 2023
PRIMARY
CAS
2942-42-9
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
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DRUG BANK
DB02207
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
NSC
72843
Created by admin on Fri Dec 15 17:58:30 GMT 2023 , Edited by admin on Fri Dec 15 17:58:30 GMT 2023
PRIMARY
FDA UNII
UX0N37CMVH
Created by admin on Fri Dec 15 17:58:30 GMT 2023 , Edited by admin on Fri Dec 15 17:58:30 GMT 2023
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WIKIPEDIA
7-Nitroindazole
Created by admin on Fri Dec 15 17:58:30 GMT 2023 , Edited by admin on Fri Dec 15 17:58:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID30183638
Created by admin on Fri Dec 15 17:58:30 GMT 2023 , Edited by admin on Fri Dec 15 17:58:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
220-934-4
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY