7-Nitroindazole

7-Nitroindazole
IUPAC name 7-nitro-1H-indazole
Identifiers
CAS number	2942-42-9
PubChem	1893
ChemSpider	1821 Y
ChEMBL	CHEMBL247378 Y
Jmol-3D images	Image 1
SMILES [O-][N+](=O)c1cccc2c1nnc2
InChI InChI=1S/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9) Y Key: PQCAUHUKTBHUSA-UHFFFAOYSA-N Y InChI=1/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9) Key: PQCAUHUKTBHUSA-UHFFFAOYAE
Properties
Molecular formula	C7H5N3O2
Molar mass	163.1335
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

7-Nitroindazole, or 7-NI, is a heterocyclic small molecule containing an indazole ring that has been nitrated at the 7 position. Nitroindazole acts as a selective inhibitor for neuronal nitric oxide synthase, a hemoprotein enzyme that, in neuronal tissue, converts arginine to citrulline and nitric oxide (NO).^[1] Nitric oxide can diffuse through the plasma membrane into neighbouring cells, allowing cell signalling, so nitroindazole indirectly inhibits this signalling process.^[2][3][4] Other inhibitors exist such as 3-bromo-7-nitroindazole, which is more potent but less specific,^[5] or NPA (N-propyl-L-arginine), which acts on a different site.^[6]

Pharmacology

7-Nitroindazole is under investigation as a possible protective agent against nerve damage caused by excitotoxicity or neurodegenerative diseases.^[1][7] It may act by reducing oxidative stress or by decreasing the amount of peroxynitrite formed in these tissues.

See also

• Dizocilpine (MK-801) a non-competitive antagonist of the NMDA receptor
• Sildenafil a drug for impotence, which inhibits cGMP specific phosphodiesterase type 5 (PDE5), which is responsible for degradation of cGMP, which is produced by guanylate cyclase, which is activated by nitric oxide produced by eNOS
• tetrahydrobiopterin, cofactor to several enzymes including nitric oxide synthase (NOS)
• protein kinase A (PKA) and protein kinase C (PKC)

References

1. ^ ^{a b} Southan GJ, Szabó C (February 1996). "Selective pharmacological inhibition of distinct nitric oxide synthase isoforms". Biochem. Pharmacol. 51 (4): 383–94. doi:10.1016/0006-2952(95)02099-3. PMID 8619882. 
2. ^ Moore PK, Wallace P, Gaffen Z, Hart SL, Babbedge RC (September 1993). "Characterization of the novel nitric oxide synthase inhibitor 7-nitro indazole and related indazoles: antinociceptive and cardiovascular effects". Br. J. Pharmacol. 110 (1): 219–24. PMC 2175981. PMID 7693278. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2175981. 
3. ^ Babbedge RC, Bland-Ward PA, Hart SL, Moore PK (September 1993). "Inhibition of rat cerebellar nitric oxide synthase by 7-nitro indazole and related substituted indazoles". Br. J. Pharmacol. 110 (1): 225–8. PMC 2175991. PMID 7693279. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2175991. 
4. ^ Moore PK, Babbedge RC, Wallace P, Gaffen ZA, Hart SL (February 1993). "7-Nitro indazole, an inhibitor of nitric oxide synthase, exhibits anti-nociceptive activity in the mouse without increasing blood pressure". Br. J. Pharmacol. 108 (2): 296–7. PMC 1907983. PMID 7680591. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1907983. 
5. ^ Gammie SC, Olaghere-da Silva UB, Nelson RJ (July 2000). "3-bromo-7-nitroindazole, a neuronal nitric oxide synthase inhibitor, impairs maternal aggression and citrulline immunoreactivity in prairie voles". Brain Res. 870 (1-2): 80–6. doi:10.1016/S0006-8993(00)02404-5. PMID 10869504. http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(00)02404-5. 
6. ^ Kampf C, Roomans GM (May 2001). "Effects of hypochlorite on cultured respiratory epithelial cells". Free Radic. Res. 34 (5): 499–511. doi:10.1080/10715760100300441. PMID 11378533. 
7. ^ Schulz JB, Matthews RT, Klockgether T, Dichgans J, Beal MF (September 1997). "The role of mitochondrial dysfunction and neuronal nitric oxide in animal models of neurodegenerative diseases". Mol. Cell. Biochem. 174 (1-2): 193–7. doi:10.1023/A:1006852306789. PMID 9309687. 

External links

• MeSH 7-nitroindazole