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{{chembox new
{{context}}
| ImageFile = 7-nitroindazole.png
{{unref}}
| ImageSize = 150
{{notable}}
| IUPACName = 7-nitro-1H-indazole
'''Nitroindazole''', also known as '''7-nitroindazole''' or '''7-NI''', is a selective inhibitor for nNOS.
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo=2942-42-9
| PubChem=1893
| SMILES=[H]n1ncc2cccc(N(=O)=O)c21
}}
| Section2 = {{Chembox Properties
| Formula=C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>2</sub>
| MolarMass=163.1335
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
| Section3 = {{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}}
}}
'''7-Nitroindazole''', or '''7-NI''', is a [[heterocyclic compound|heterocyclic]] [[small molecule]] containing an [[indazole]] ring which has been [[nitration|nitrated]] at the 7 position. Nitroindazole acts as a selective inhibitor for [[neuron]]al [[nitric oxide synthase]], a hemoprotein [[enzyme]] which in [[neuron]]al tissue converts [[arginine]] to [[citrulline]] and [[nitric oxide]] (NO).<ref name=Southan>{{cite journal |author=Southan GJ, Szabó C |title=Selective pharmacological inhibition of distinct nitric oxide synthase isoforms |journal=Biochem. Pharmacol. |volume=51 |issue=4 |pages=383–94 |year=1996 |month=February |pmid=8619882}}</ref> Nitric oxide can diffuse through the plasma membrane into neighbouring cells, allowing [[cell signalling]], so nitroindazole indirectly inhibits this signalling process.<ref name="pmid7693278">{{cite journal | author = Moore PK, Wallace P, Gaffen Z, Hart SL, Babbedge RC | title = Characterization of the novel nitric oxide synthase inhibitor 7-nitro indazole and related indazoles: antinociceptive and cardiovascular effects | journal = Br. J. Pharmacol. | volume = 110 | issue = 1 | pages = 219–24 | year = 1993 | month = September | pmid = 7693278 | doi = | url = | issn = }}</ref><ref name="pmid7693279">{{cite journal | author = Babbedge RC, Bland-Ward PA, Hart SL, Moore PK | title = Inhibition of rat cerebellar nitric oxide synthase by 7-nitro indazole and related substituted indazoles | journal = Br. J. Pharmacol. | volume = 110 | issue = 1 | pages = 225–8 | year = 1993 | month = September | pmid = 7693279 | doi = | url = | issn = }}</ref><ref name="pmid7680591">{{cite journal | author = Moore PK, Babbedge RC, Wallace P, Gaffen ZA, Hart SL | title = 7-Nitro indazole, an inhibitor of nitric oxide synthase, exhibits anti-nociceptive activity in the mouse without increasing blood pressure | journal = Br. J. Pharmacol. | volume = 108 | issue = 2 | pages = 296–7 | year = 1993 | month = February | pmid = 7680591 | doi = | url = | issn = }}</ref> Other inhibitors exist such as 3-bromo-7-nitroindazole, which is more potent but less specific,<ref name="pmid10869504">{{cite journal | author = Gammie SC, Olaghere-da Silva UB, Nelson RJ | title = 3-bromo-7-nitroindazole, a neuronal nitric oxide synthase inhibitor, impairs maternal aggression and citrulline immunoreactivity in prairie voles | journal = Brain Res. | volume = 870 | issue = 1-2 | pages = 80–6 | year = 2000 | month = July | pmid = 10869504 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(00)02404-5 | issn = }}</ref> or NPA ([[N-propyl-L-arginine]]), which acts on a different site.<ref name="pmid11378533">{{cite journal | author = Kampf C, Roomans GM | title = Effects of hypochlorite on cultured respiratory epithelial cells | journal = Free Radic. Res. | volume = 34 | issue = 5 | pages = 499–511 | year = 2001 | month = May | pmid = 11378533 | doi = | url = | issn = }}</ref>

==Pharmacology==
7-Nitroindazole is under investigation as a possible protective agent against [[nerve damage]] caused by [[excitotoxicity]] or [[neurodegenerative disease]]s.<ref name=Southan/><ref>{{cite journal |author=Schulz JB, Matthews RT, Klockgether T, Dichgans J, Beal MF |title=The role of mitochondrial dysfunction and neuronal nitric oxide in animal models of neurodegenerative diseases |journal=Mol. Cell. Biochem. |volume=174 |issue=1-2 |pages=193–7 |year=1997 |month=September |pmid=9309687}}</ref> 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)

[[Category:Nitrogen heterocycles]]
[[Category:Inhibitors]]

==References==
{{Reflist|2}}

==External links==
* {{MeshName|7-nitroindazole}}
* [http://www.ncbi.nlm.nih.gov/sites/entrez?term=%227-nitroindazole%22%5BNM%5D&cmd=search&db=pubmed PubMed articles on 7-nitroindazole]

Revision as of 20:45, 9 May 2008

Template:Chembox new 7-Nitroindazole, or 7-NI, is a heterocyclic small molecule containing an indazole ring which has been nitrated at the 7 position. Nitroindazole acts as a selective inhibitor for neuronal nitric oxide synthase, a hemoprotein enzyme which 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

References

  1. ^ a b Southan GJ, Szabó C (1996). "Selective pharmacological inhibition of distinct nitric oxide synthase isoforms". Biochem. Pharmacol. 51 (4): 383–94. PMID 8619882. {{cite journal}}: Unknown parameter |month= ignored (help)
  2. ^ Moore PK, Wallace P, Gaffen Z, Hart SL, Babbedge RC (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. PMID 7693278. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Babbedge RC, Bland-Ward PA, Hart SL, Moore PK (1993). "Inhibition of rat cerebellar nitric oxide synthase by 7-nitro indazole and related substituted indazoles". Br. J. Pharmacol. 110 (1): 225–8. PMID 7693279. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Moore PK, Babbedge RC, Wallace P, Gaffen ZA, Hart SL (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. PMID 7680591. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. ^ Gammie SC, Olaghere-da Silva UB, Nelson RJ (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. PMID 10869504. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  6. ^ Kampf C, Roomans GM (2001). "Effects of hypochlorite on cultured respiratory epithelial cells". Free Radic. Res. 34 (5): 499–511. PMID 11378533. {{cite journal}}: Unknown parameter |month= ignored (help)
  7. ^ Schulz JB, Matthews RT, Klockgether T, Dichgans J, Beal MF (1997). "The role of mitochondrial dysfunction and neuronal nitric oxide in animal models of neurodegenerative diseases". Mol. Cell. Biochem. 174 (1–2): 193–7. PMID 9309687. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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