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Nω-Nitro-l -arginine
Names
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
Identifiers
ChEMBL
ECHA InfoCard
100.016.745
UNII
OC([C@@H](N)CCCNC(N[N+]([O-])=O)=N)=O
Properties
C 6 H 13 N 5 O 4
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).
Chemical compound
Nitroarginine , or N ω -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, N ω -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.
Forms
Targets
NO donors (
prodrugs )
Enzyme (
inhibitors )
Others
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 )