Nitroarginine
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| IUPAC name (2S)-2-Amino-5-[[amino(nitramido)methylidene]amino]pentanoic acid | |
| Other names N5-(nitroamidino)-l-Ornithine; (+)-NG-Nitroarginine; NG-nitro-l-Arginine, l-NG-Nitroarginine; L-NNA; L-NOARG; NG-Nitro-l-arginine; NG-Nitroarginine; NOLA; NSC 53662; Nitro-l-arginine; Nω-Nitro-l-arginine; Nω-Nitro-l-arginine; ω-Nitro-l-arginine; ω-Nitroarginine | |
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| ECHA InfoCard | 100.016.745  |
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| Properties | |
Chemical formula | C6H13N5O4 |
| Molar mass | 219.201 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).  N verify (what is  Y N ?) Infobox references | |
Chemical compound
Nitroarginine, or Nω-nitro-l-arginine, also known as L-NOARG, is a nitro derivative of the amino acid arginine.[1] It is an inhibitor of nitric oxide synthase and hence a vasoconstrictor. As such, it finds widespread use as a biochemical tool in the study of nitric oxide and its biological effects.[2]
Nitroarginine has been used in research studying coronary constriction, and it was found that, in the presence of midazolam vasodilatation was unaffected by nitroarginine.[3] Due to the presence of all three isoforms of nitric oxide synthase in striatal tissue in the forebrain, research has also been conducted on how its inhibition might affect monoamine transport and dopamine half-life in the striatal extracellular space.[4]
References
- ^ Moore, P. K.; Al‐Swayeh, O. A.; Chong, N. W. S.; Evans, R. A.; Gibson, A. (1990). "l-NG-nitro arginine (l-NOARG), a novel, l-arginine-reversible inhibitor of endothelium-dependent vasodilatation in vitro". British Journal of Pharmacology. 99 (2): 408–412. doi:10.1111/j.1476-5381.1990.tb14717.x. ISSN 1476-5381. PMC 1917379. PMID 2328404.
- ^ Bansinath M, Arbabha B, Turndorf H, Garg UC (1993). "Chronic administration of a nitric oxide synthase inhibitor, Nω-nitro-L-arginine, and drug-induced increase in cerebellar cyclic GMP in vivo". Neurochemical Research. 18 (10): 1063–6. doi:10.1007/BF00966685. PMID 7504789. S2CID 2447933.
- ^ O.L. Woodman; G.J. Dusting (1991). "N-nitro L-arginine causes coronary vasoconstriction and inhibits endothelium-dependent vasodilatation in anaesthetized greyhounds". Br. J. Pharmacol. 103 (2): 1407–1410. doi:10.1111/j.1476-5381.1991.tb09802.x. PMC 1908370. PMID 1909199.
- ^ Prieto, Sonia Guerrero; Silva, João Carlos dos Santos; de Lima, Mairon Oliveira; Almeida, Maria Camila; Echeverry, Marcela Bermúdez (February 2019). "Cross-tolerance between nitric oxide synthase inhibition and atypical antipsychotics modify nicotinamide-adenine-dinucleotide phosphate-diaphorase activity in mouse lateral striatum". Behavioural Pharmacology. 30 (1): 67–78. doi:10.1097/FBP.0000000000000406. ISSN 0955-8810. PMID 29664745. S2CID 4933721 – via Ovid.
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- Nitroxyl anion (NO−; oxonitrate(1-), hyponitrite anion)
- Nitric oxide (NO⋅; nitrogen monoxide)
- Nitrosonium (NO+; nitrosyl cation)
| sGC |
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(prodrugs)
- Nitrates: Diethylene glycol dinitrate (DEGDN)
- Erythritol tetranitrate (ETN)
- Ethylene glycol dinitrate (EGDN; nitroglycol)
- Isosorbide mononitrate (ISMN)
- Isosorbide dinitrate (ISDN)
- Itramin tosilate
- Mannitol hexanitrate
- Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
- NCX-466
- NCX-2216
- NCX-4016
- NCX 4040
- NCX-4215
- Nicorandil
- Nipradilol (K-351)
- Nitrate (NO−
3) - Nitroatorvastatin (NCX-6560)
- Nitroflurbiprofen (HCT-1026)
- Nitrofluvastatin
- Nitroglycerin (glyceryl trinitrate (GTN))
- Nitropravastatin (NCX-6550)
- Pentaerithrityl tetranitrate (PETN)
- Propatylnitrate
- Propylene glycol dinitrate (PGDN)
- Sodium trioxodinitrate (Angeli's salt)
- Tenitramine
- Trolnitrate
- Nitroso compounds/nitrites: Nitrite (NO−
2); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite) - Cyclohexyl nitrite
- Ethyl nitrite
- Hexyl nitrite
- Isobutyl nitrite (2-methylpropyl nitrite)
- Isopropyl nitrite
- Methyl nitrite
- n-Butyl nitrite
- Pentyl nitrite
- tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810
- S-Nitrosoalbumin (SNALB)
- S-Nitrosated AR545C
- S-Nitroso-N-acetylcysteine (SNAC)
- S-Nitroso-N-acetylpenicillamine (SNAP)
- S-Nitroso-N-valerylpenicillamine (SNVP)
- S-Nitrosocaptopril (SNO-Cap)
- S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
- S-Nitrosodiclofenac
- S-Nitrosoglutathione (GSNO, SNOG)
- SNO-t-PA
- SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A
- Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt
- Roussin's red salt
- Sodium nitroprusside (SNP)
- NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
- Diethylenetriamine/NO (DETA/NO)
- GLO/NO
- JS-K
- Methylamine hexamethylene methylamine/NO (MAHMA/NO)
- PROLI/NO
- Spermine/NO (SPER/NO)
- V-PYRRO/NO
- Heterocyclic compounds: Furoxans: Furoxan
- REC15/2739; Sydnonimines: Feprosidnine
- Linsidomine (SIN-1)
- Molsidomine (SIN-10)
- Sydnonimine
- Unsorted: Cimlanod
- FK-409
- FR144220
- FR146881
- N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
(inhibitors)
| NOS |
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| Arginase |
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- Precursors: L-Arginine
- Nω-Hydroxy-L-arginine (NOHA)
- Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
- ETB receptor antagonists (e.g., bosentan)
- L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
- Nebivolol (beta blocker)
- PDE5 inhibitors (e.g., sildenafil)
- non-selective PDE inhibitors (e.g., caffeine)
- PDE9 inhibitors (e.g., paraxanthine)
- cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
- Statins (e.g., simvastatin)
See also: Receptor/signaling modulators
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