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(4S)-N-(4-amino-5-[aminoethyl]aminopentyl)-N''-nitroguanidine
-
1,5,6,7-tetrahydro-2H-azepin-2-imines
-
-
1-phenylimidazole
-
reversible inhibition of endothelial enzyme, competitive versus L-arginine and tetrahydrobiopterin, no inhibition of cytochrome c reduction
2',3'-dialdehyde of NADPH
-
at concentrations of 40times the apparent Km-value or after prolonged incubation, independent of Ca2+/calmodulin, L-arginine or tetrahydrobiopterin, NADPH prevents inhibition, the NADPH-diaphorase activity of the enzyme is less sensitive than the nitric oxide synthase activity
2-aminopyridine derivatives
highly selective inhibitors
-
3,4-dihydro-1-isoquinolinamines
-
-
3-bromo-7-nitroindazole
nNOS-specific inhibitor, complete inhibition at 0.01 mM
3-[cis-4'-[(6''-aminopyridin-2''-yl)methyl]pyrrolidin-3'-ylamino]propan-1-ol
-
4-(3-amino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
4-(3-amino-propoxy)-6-chloro-1H-quinolin-2-one trifluoroacetic acid salt
IC50: 410 nM, pharmacokinetic profile
4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
4-(3-dimethylamino-propoxy)-1H-quinolin-2-one
4-oxononenal
ONE, a highly bioreactive agent, able to inhibit eNOS activity and NO production. It can posttranslationally modify the enzyme in the placenta
-
5,6,7,8-tetrahydrobiopterin
-
quenches the uncoupled reactions and results in much less reactive oxygen species formation, whereas the presence of redox-incompetent 7,8-dihydrobiopterin demonstrates little quenching effect
6(R,S)-methyl-5-deazatetrahydropterin
-
-
6-([[(3R,5S)-5-[[(6-amino-4-methylpyridin-2-yl)methoxy]methyl]pyrrolidin-3-yl]oxy]methyl)-4-methylpyridin-2-amine
exhibits antimicrobial properties
6-chloro-4-(3-aminopropoxy)-1-benzopyran-2-one trifluoroacetic acid salt
6-chloro-4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt
6-n-propyl-2-thyouracil
0.1 mg 6-n-propyl-2-thyouracil decreases nNOS activity to 45% compared to control
6-[[(2S,3S)-2-amino-3-[(6-amino-4-methylpyridin-2-yl)methoxy]butoxy]methyl]-4-methylpyridin-2-amine
exhibits antimicrobial properties
A-23187
high levels of A-23187 inhibit nNOS activity
agmatine
-
at lower concentration than the Ki value agmatine leads to time-, concentration-, NADPH- and calmodulin-dependent inhibition of the neuronal enzyme in presence of calmodulin; causes an increase in NADPH oxidase activity of the enzyme
carbon monoxide
carbon monoxide down-regulates iNOS activity by reducing its expression level or by inhibiting its activity by converting it to an inactive P420 form, the presence of dithiothreitol, L-Arg, or H4B partially inhibits the iNOSP450 to iNOSP420 conversion, whereas the presence of both L-Arg and 5,6,7,8-tetrahydro-L-biopterin completely prevents the transition
CO/O2
-
80%:20%, mixture
-
Di-2-thienyliodonium
-
competitive, irreversible, complete, time and temperature dependent inhibition
ethylene glycol bis(beta-amino-ethylether)-N,N,N',N'-tetraacetic acid
Gly-methyl-L-arginine
-
inhibition of the isozymes in absence or presence of L-arginine
H2O2
-
alters heme group, decrease in activity
Iodoniumdiphenyl
-
competitive, irreversible, complete, time and temperature dependent inhibition
L-arginine methyl ester
-
L-Asn-methyl-L-arginine
-
inhibition of the isozymes in absence or presence of L-arginine
L-N-methylarginine
NOS inhibitor, complete inhibition at 0.5 mM; NOS inhibitor, complete inhibition at 0.5 mM; NOS inhibitor, complete inhibition at 0.5 mM
L-N6-(1-iminoethyl)lysine dihydrochloride
-
5 mM, 78% inhibition
L-NG-monomethyl arginine
L-NMMA
-
L-NG-nitro-arginine-methylester
-
-
L-Nomega-nitroarginine-(4R)-amino-L-proline amide
-
L-Nomega-nitroarginine-2,4-L-diaminobutyramide
-
L-omega-monomethyl L-arginine
potent competitive eNOS inhibitor, complete inhibition at 10 mM
MeHg
methylmercury, impact of chronic MeHg intoxication on NADPH diaphorase (NADPH-d) activity and astrocyte mobilization in the visual cortex of the rat, overview. MeHg accumulates in the central nervous system (CNS) and preferentially accumulates in astrocytes, and it causes several neurotoxic effects, such as visual-field constriction, cerebellar ataxia and multimodal sensory disorders. MeHg-intoxicated animals display a significant decrease of NADPH-d neuropil reactivity across the visual cortex when compared to controls. The decreased neuropil reactivity to NADPH-d may also be related to MeHg-induced astrocytic dysfunction
-
methylisothiourea
-
0.01 mM, about 80% residual activity
N(G),N(G)-dimethyl-L-arginine
-
asymmetric dimethyl arginine
N(G)-nitroarginine methyl ester
-
N-(4-aminobutyl)-5-chloro-2-naphthalene sulfonamide
-
-
N-(6-Aminohexyl)-1-naphthalene sulfonamide
-
-
N-(6-aminohexyl)-5-chloro-1-naphthalene sulfonamide
-
calmodulin antagonist above 0.01 mM; i.e. W-7
N-iminoethyl-L-lysine
no isozyme specificity
N-iminoethyl-L-ornithine
no isozyme specificity
N-monomethyl-L-arginine
-
0.01 mM, about 55% residual activity
N-nitro-L-arginine methyl ester
N-omega-nitro-L-arginine
-
N-[(1,3-benzodioxol-5-yl)methyl]-1-[2-(1H-imidazol-1-yl)pyrimidin-4-yl]-4-(methoxycarbonyl)-piperazine-2-acetamide
inhibition of dimer formation in vivo and in vitro, efficiency is dependent on enzyme source
N1-[cis-4'-[(6''-amino-4''-methylpyridin-2''-yl)methyl]pyrrolidin-3'-yl]-N2-(4'-chlorobenzyl)ethane-1,2-diamine
-
N1-[cis-4'-[(6''-aminopyridin-2''-yl)methyl]pyrrolidin-3'-yl]ethane-1,2-diamine
-
N1-[trans-4'-[(6''-amino-4''-methylpyridin-2''-yl)methyl]pyrrolidin-3'-yl]-N2-(3'-chlorobenzyl)ethane-1,2-diamine
-
nanoshutter NS1
mixture of (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-([2-(ethyl(4-[(E)-2-(4-nitrophenyl)ethenyl]phenyl)amino)ethyl]carbamoyl)-4-hydroxyoxolan-3-yl dihydrogen phosphate and (2R,3R,4R,5S)-2-(6-amino-9H-purin-9-yl)-5-([2-(ethyl(4-[(E)-2-(4-nitrophenyl)ethenyl]phenyl)amino)ethyl]carbamoyl)-4-hydroxyoxolan-3-yl dihydrogen phosphate. The NOS inhibitor targets the reductase domain of the enzyme
-
NG-methyl arginine
-
specific inhibition
NG-methyl-L-arginine
no isozyme specificity
Ng-monomethy-L-arginine
-
-
Ngamma,Ngamma-dimethyl-L-arginine
Ngamma-amino-L-arginine
-
-
Ngamma-hydroxy-Ngamma-methyl-L-arginine
-
preincubation at 37°C leads to irreversible inactivation, substrates protect
Ngamma-iminoethyl-L-ornithine
-
competitive inhibitor
Ngamma-monomethyl-L-arginine
Ngamma-nitro-L-arginine methyl ester
Nomega-nitro-L-arginine methyl ester
Nomega-nitro-L-arginine methylester
-
NXN-188
-
a dual-action oral therapeutic being developed for the treatment of acute migraine. The pharmacological mechanism of action of NXN-188 involves inhibition of both the neuronal nitric oxide synthase enzyme isoform and affinity for serotonin receptors. Clinical studies and pharmacokinetics, detailed overview
PIN
-
human protein enzyme inhibitor, recombinantly expressed in Escherichia coli, the recombinant CREB-binding protein-bound inhibitor protein is purified by calmodulin affinity and inhibits the enzyme to a high extent at 0.001 mM
-
tetrahydrobiopterin
-
inhibits peroxynitrite activation
W7 hydrochloride
-
5 mM, 50% inhibition
4-(3-amino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
-
IC50: 0.0076 mM
4-(3-amino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
IC50: 0.0119 mM
4-(3-amino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
-
IC50: 0.0091 mM
4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
-
IC50: 0.004 mM
4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
IC50: 0.01 mM
4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
-
IC50: 0.01 mM
4-(3-dimethylamino-propoxy)-1H-quinolin-2-one
-
IC50: 0.0026 mM
4-(3-dimethylamino-propoxy)-1H-quinolin-2-one
IC50: 0.0104 mM
4-(3-dimethylamino-propoxy)-1H-quinolin-2-one
-
IC50: 0.010 mM
6-chloro-4-(3-aminopropoxy)-1-benzopyran-2-one trifluoroacetic acid salt
-
IC50: 90 nM, pharmacokinetic profile
6-chloro-4-(3-aminopropoxy)-1-benzopyran-2-one trifluoroacetic acid salt
IC50: 60 nM, pharmacokinetic profile
6-chloro-4-(3-aminopropoxy)-1-benzopyran-2-one trifluoroacetic acid salt
-
IC50: 0.00056 mM, pharmacokinetic profile
6-chloro-4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
-
IC50: 0.0041 mM
6-chloro-4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
IC50: 0.0012 mM
6-chloro-4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
-
IC50: 0.008 mM
6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt
-
IC50: 0.00011mM
6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt
IC50: 0.00025mM
6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt
-
IC50: 0.00053mM
7-nitroindazole
-
7-nitroindazole
-
reversible inhibition of endothelial enzyme, competitive versus tetrahydrobiopterin, no inhibition of cytochrome c reduction
7-nitroindazole
-
weak inhibition
7-nitroindazole
-
neuronal NOS inhibitor
7-nitroindazole
-
inhibits the neuronal NOS in vivo and reduces L-DOPA-induced dyskinesias in a rat model of parkinsonism. The rats show a lack of tolerance for the anti-dyskinetic effects
aminoguanidine
-
-
aminoguanidine
-
0.01 mM, about 40% residual activity
AR-C102222
1,2-dihydro-4-quinazolinamine derivative
AR-C102222
-
1,2-dihydro-4-quinazolinamine derivative
AR-C85016
1,2-dihydro-4-quinazolinamine derivative
AR-C85016
-
1,2-dihydro-4-quinazolinamine derivative
AR-R17477
-
-
Ca2+
-
preincubation at 37°C leads to time-dependent inhibition of the enzyme
Ca2+
high levels of Ca2+ inhibit nNOS activity
Calmidazolium
-
-
Calmidazolium
-
calmodulin antagonist; complete inhibition
Calmidazolium
-
calmodulin antagonist
Calmidazolium
-
in absence of calmodulin
CO
-
-
CO
-
partially purified rat cerebellum enzyme
cyanide
-
heme-blocker inhibits superoxide formation after pretreatment of the enzyme
diphenylene iodonium
-
inhibition of superoxide production of recombinant isoform III
diphenylene iodonium
-
competitive, irreversible, complete, time and temperature dependent inhibition
EDTA
-
inhibits at concentrations above 0.01 mM
ethylene glycol bis(beta-amino-ethylether)-N,N,N',N'-tetraacetic acid
-
i.e. EGTA, complete inhibition of cytosolic enzyme, partial inhibition of particulate enzyme
ethylene glycol bis(beta-amino-ethylether)-N,N,N',N'-tetraacetic acid
-
-
ethylene glycol bis(beta-amino-ethylether)-N,N,N',N'-tetraacetic acid
-
i.e. EGTA, complete inhibition of cytosolic enzyme, partial inhibition of particulate enzyme
ethylene glycol bis(beta-amino-ethylether)-N,N,N',N'-tetraacetic acid
-
i.e. EGTA, complete inhibition of cytosolic enzyme, partial inhibition of particulate enzyme
imidazole
-
the enzyme forms a sixcoordinate low-spin complex with inhibitor imidazole, interaction analysis
imidazole
-
inhibition of the endothelial enzyme, competitive versus L-arginine, no inhibition of cytochrome c reduction
imidazole
-
heme-blocker inhibits superoxide formation after pretreatment of the enzyme
inhibitor NS1
-
is a new prototype of a reversible inhibitor of constitutive NOS targeting their reductase domain. NS1 is designed by molecular modelling, by replacing the imbedded NADP cofactor in neuronal NOS reductase domain. NS1 shares with NADPH the nucleotide moiety that allows proper targeting to the NADPH site. NS1 competes with NADPH binding
inhibitor NS1
is a new prototype of a reversible inhibitor of constitutive NOS targeting their reductase domain. NS1 is designed by molecular modelling, by replacing the imbedded NADP cofactor in neuronal NOS reductase domain. NS1 shares with NADPH the nucleotide moiety that allows proper targeting to the NADPH site. NS1 competes with NADPH binding
L-arginine
-
inhibits peroxynitrite activation
L-arginine
-
L-arginine strongly stimulates oxygen consumption of eNOS and inhibits that of nNOS
L-canavanine
-
not inhibitory
L-canavanine
-
liver enzyme, slight inhibition of brain enzyme
L-thiocitrulline
-
5 mM, above 95% inhibition
L-thiocitrulline
no isozyme specificity
N-nitro-L-arginine methyl ester
-
0.5 mM, 65% inhibition
N-nitro-L-arginine methyl ester
-
1 mM, about 50% residual activity
N-nitro-L-arginine methyl ester
-
competitive NOS inhibitor
N-nitro-L-arginine methyl ester
-
0.01 mM, about 40% residual activity
NG-Nitro-L-arginine
no isozyme specificity
NG-Nitro-L-arginine
complete inhibition at 1 mM, non-selective NOS inhibitor; complete inhibition at 1 mM, non-selective NOS inhibitor
Ngamma,Ngamma-dimethyl-L-arginine
-
-
Ngamma,Ngamma-dimethyl-L-arginine
-
-
Ngamma-monomethyl-L-arginine
-
-
Ngamma-monomethyl-L-arginine
-
inhibits citrulline formation, not cytochrome c reduction
Ngamma-monomethyl-L-arginine
-
-
Ngamma-monomethyl-L-arginine
-
-
Ngamma-monomethyl-L-arginine
-
-
Ngamma-monomethyl-L-arginine
-
endothelial and neuronal isoforms: reversible inhibition; L-arginine protects against enzyme inactivation, thus inactivation occurs at or near active site
Ngamma-monomethyl-L-arginine
-
-
Ngamma-monomethyl-L-arginine
-
inducible isoform: after preincubation irreversible, time- and concentration-dependent inactivation, without preincubation reversible inhibition; L-arginine protects against enzyme inactivation, thus inactivation occurs at or near active site
Ngamma-monomethyl-L-arginine
-
slightly
Ngamma-monomethyl-L-arginine
-
-
Ngamma-monomethyl-L-arginine
-
not D-isomer, strong, competitive
Ngamma-monomethyl-L-arginine
-
slightly
Ngamma-monomethyl-L-arginine
-
endothelial and neuronal isoforms: reversible inhibition; in presence of tetrahydrobiopterin 0.004 mM the neuronal isoform is inactivated; L-arginine protects against enzyme inactivation, thus inactivation occurs at or near active site
Ngamma-nitro-L-arginine
-
-
Ngamma-nitro-L-arginine
-
inhibits citrulline formation, not cytochrome c reduction
Ngamma-nitro-L-arginine
-
-
Ngamma-nitro-L-arginine
-
-
Ngamma-nitro-L-arginine
-
-
Ngamma-nitro-L-arginine
-
irreversible inactivation of neuronal and endothelial isoform after preincubation, unaffected by tetrahydrobiopterin; L-arginine protects against enzyme inactivation, thus inactivation occurs at or near active site
Ngamma-nitro-L-arginine
-
-
Ngamma-nitro-L-arginine
-
L-arginine protects against enzyme inactivation, thus inactivation occurs at or near active site; reversible inhibitor of inducible isoform from macrophage
Ngamma-nitro-L-arginine
-
-
Ngamma-nitro-L-arginine
-
-
Ngamma-nitro-L-arginine
-
competitive inhibitor
Ngamma-nitro-L-arginine
-
irreversible inactivation of neuronal and endothelial isoform after preincubation, unaffected by tetrahydrobiopterin; L-arginine protects against enzyme inactivation, thus inactivation occurs at or near active site
Ngamma-nitro-L-arginine methyl ester
-
-
Ngamma-nitro-L-arginine methyl ester
-
complete inhibition
Ngamma-nitro-L-arginine methyl ester
-
only L-isomer, inhibits NO and citrulline production from L-arginine as well as superoxide formation in absence of tetrahydropterin
Ngamma-nitro-L-arginine methyl ester
-
-
Ngamma-nitro-L-arginine methyl ester
-
-
Ngamma-nitro-L-arginine methyl ester
-
very slightly, only L-isomer and in presence of tetrahydrobiopterin and NADPH
Ngamma-nitro-L-arginine methyl ester
-
nearly complete inhibition at 0.5 mM
nitroblue tetrazolium
-
-
nitroblue tetrazolium
-
potent non-competitive inhibitor, partially reversible by tetrahydrobiopterin
nitroblue tetrazolium
-
-
Nomega-nitro-L-arginine methyl ester
-
nonselective NOS inhibitor
Nomega-nitro-L-arginine methyl ester
-
Nomega-nitro-L-arginine methylester
L-NAME, the NOS inhibitor targets the oxygenase domain of the enzyme
-
Nomega-nitro-L-arginine methylester
L-NAME, an inhibitor of iNOS
-
S-ethylisothiourea
-
5 mM, 85% inhibition
S-ethylisothiourea
-
inducible NOS inhibitor
thiocoumarin
-
IC50: 0.018 mM
thiocoumarin
weak inhibitor
Trifluoperazine
-
inhibits cytochrome c reductase activity
Trifluoperazine
-
inhibition in the presence of Ca2+, reversible by calmodulin
Trifluoperazine
-
no inhibitor of macrophage enzyme
Trifluoperazine
-
no inhibitor of macrophage enzyme
Trifluoperazine
-
in absence of calmodulin
additional information
-
not inhibitory: N-nitro-D-arginine methyl ester at 0.5 mM
-
additional information
a protein-based system is developed in which ligand inhibition can be rapidly evaluated in vitro
-
additional information
-
Ngamma,Ngamma'-dimethyl-L-arginine has no inhibitory effect
-
additional information
-
no inhibition by 4-(3-amino-propoxy)-6-chloro-1H-quinolin-2-one trifluoroacetic acid salt
-
additional information
interleukin-1 induces the degradation of isozyme iNOS, iNOS protein levels in osteoarthritic chondrocytes decreases to 45.4% of the control upon treatment with interleukin-1 for 15 min, and are further reduced to 41.5% when the treatment period is extended to 2 h; tissue necrosis factor-alpha induces nNOS disappearance, interleukin-1 induces the degradation of nNOS
-
additional information
interleukin-1 induces the degradation of isozyme iNOS, iNOS protein levels in osteoarthritic chondrocytes decreases to 45.4% of the control upon treatment with interleukin-1 for 15 min, and are further reduced to 41.5% when the treatment period is extended to 2 h; tissue necrosis factor-alpha induces nNOS disappearance, interleukin-1 induces the degradation of nNOS
-
additional information
-
interleukin-1 induces the degradation of isozyme iNOS, iNOS protein levels in osteoarthritic chondrocytes decreases to 45.4% of the control upon treatment with interleukin-1 for 15 min, and are further reduced to 41.5% when the treatment period is extended to 2 h; tissue necrosis factor-alpha induces nNOS disappearance, interleukin-1 induces the degradation of nNOS
-
additional information
-
fibroblast growth factor-2 treatment up-regulates the enzyme in tectume, but down-regulates it in the optic nerve, overview
-
additional information
-
the macrophage enzyme is not inhibited by calmodulin antagonists (N-4-aminobutyl-), (N-6-aminohexyl)-5-chloro-2-naphthalene sulfonamide
-
additional information
-
not inhibitory: N-nitro-L-arginine methyl ester, or specific inhibitor of inducible NOS, 1400W
-
additional information
inhibitory activity for coumarin derivatives, inhibitor screening, overview
-
additional information
-
inhibitory activity for coumarin derivatives, inhibitor screening, overview
-
additional information
-
inhibition of PSD-95/nNOS interaction by the nNOSalpha beta-finger antibody
-
additional information
-
although H4B binding seems unable to affect iNOSoxy capacity to activate peroxynitrite decomposition, the binding of Arg and citrulline at the distal side of the heme pocket drastically reduces peroxynitrite activation
-
additional information
there is decreased eNOS activity in tight-skin 1-mouse skin tissue
-
additional information
-
there is decreased eNOS activity in tight-skin 1-mouse skin tissue
-
additional information
-
no inhibitor of NADPH-diaphorase activity: methotrexate
-
additional information
-
the macrophage enzyme is not inhibited by calmodulin antagonists (N-4-aminobutyl-), (N-6-aminohexyl)-5-chloro-2-naphthalene sulfonamide; the macrophage enzyme is not inhibited by calmodulin antagonists (N-6-aminohexyl)-1-naphthalene sulfonamide
-
additional information
-
the macrophage enzyme is not inhibited by calmodulin antagonists (N-4-aminobutyl-), (N-6-aminohexyl)-5-chloro-2-naphthalene sulfonamide; the macrophage enzyme is not inhibited by calmodulin antagonists (N-6-aminohexyl)-1-naphthalene sulfonamide
-
additional information
-
no inhibition by 4-(3-amino-propoxy)-6-chloro-1H-quinolin-2-one trifluoroacetic acid salt and thiocoumarin
-
additional information
-
ethanol intake reduces eNOS and increases iNOS protein levels, while mRNA levels remain unaffected in female rat aorta
-
additional information
-
inhibition of PSD-95/nNOS interaction by the nNOSalpha beta-finger antibody
-
additional information
anthrax lethal factor potentially cleaves the regions (L191-Q192 and D264-N265) close to the NH2-terminus of neuronal nitric oxide synthase; inducible nitric oxide synthase is resistant to anthrax lethal factor-mediated cleavage
-
additional information
anthrax lethal factor potentially cleaves the regions (L191-Q192 and D264-N265) close to the NH2-terminus of neuronal nitric oxide synthase; inducible nitric oxide synthase is resistant to anthrax lethal factor-mediated cleavage
-
additional information
paraformaldehyde fixation of rat brain abolishes NOS activity in particulate and cytosolic fractions
-