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Chemical Compound Review

CHEMBL332148     (2S)-5- (diaminomethylideneamino)- 2...

Synonyms: AG-K-78147, CHEBI:301445, AC1Q5QTK, CTK1A4264, AR-1J3355, ...
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Disease relevance of N-Monomethyl-L-arginine

  • Vascular effects of vitamin C (25 mg/min IA) and placebo were determined at rest and during reactive hyperemia (causing endothelium-mediated dilation) before and after intra-arterial infusion of N-monomethyl-L-arginine (L-NMMA) to inhibit endothelial synthesis of nitric oxide [1].
  • In a cell-based iNOS assay (A-172 astrocytoma cells) the inhibitors had low-nanomolar IC(50) values and thus were >1,000-fold more potent than the substrate-based direct iNOS inhibitors 1400W and N-methyl-l-arginine [2].
  • Overexpression of dimethylarginine dimethylaminohydrolase (DDAH), which metabolizes the endogenous inhibitors of NO synthesis asymmetric dimethylarginine and N-monomethyl-L-arginine, results in C6 gliomas with enhanced growth rate compared with wild type [3].
  • Oral treatment of rats with N-methyl-l -arginine acetate (l -NMA), beginning at peak disease on day 11 postimmunization, results in significant prolongation of disease and an alteration in the presentation of clinical symptoms from that of solely hind limb paresis/paralysis to severe fore limb involvement as well [4].
  • When cocultured with infected murine neuroblastoma N18 cells, gamma interferon-activated RAW 264.7 cells also efficiently hindered JEV replication in contiguous bystanders, and this anti-JEV effect could be reversed by an NO synthase (NOS) inhibitor, N-monomethyl-L-arginine acetate [5].

High impact information on N-Monomethyl-L-arginine

  • NO was released from the hepatic vasculature in a time-dependent manner, and administration of N-monomethyl-L-arginine reduced NO release and increased portal pressure [6].
  • We also analyzed IRP1 mRNA levels by Northern blotting and found a decrease in IRP1 mRNA expression after stimulation with IFN-gamma plus lipopolysaccharide, which was abrogated in the presence of N-monomethyl-l-arginine [7].
  • Down-regulation of IRP1 protein levels was correlated with the amount of NO produced and was partially abolished by the NO synthase (NOS) inhibitor N-monomethyl-l-arginine [7].
  • Addition of N-methyl-L-arginine (NMA), an NO synthase inhibitor, to the medium inhibited NO production by 90% of all stimulated cells, partially reduced doubling time of cells stimulated with LPS or IFN-gamma, and partially increased viability and growth rates in those exposed to both LPS and IFN-gamma [8].
  • The responses also were antagonized by atropine (10(-7) mol/L, n = 6), which inhibits release of endothelium-derived relaxing factor (EDRF), and by N-monomethyl-L-arginine (10(-5) mol/L, n = 6), a specific blocker of nitric oxide formation (primary relaxing factor responsible for acetylcholine vasorelaxation) [9].

Chemical compound and disease context of N-Monomethyl-L-arginine


Biological context of N-Monomethyl-L-arginine


Anatomical context of N-Monomethyl-L-arginine


Associations of N-Monomethyl-L-arginine with other chemical compounds


Gene context of N-Monomethyl-L-arginine


Analytical, diagnostic and therapeutic context of N-Monomethyl-L-arginine

  • Previously, we reported that oral administration of the NO synthase inhibitor N-methyl-L-arginine acetate (L-NMA) to recovered rats precipitated a second episode of disease in 100% of animals [32].
  • METHODS: Recombinant human IL-1beta and NOS inhibitors with different selectivity for inducible NOS (N-monomethyl-L-arginine [L-NMA], N-iminoethyl-L-ornithine [L-NIO], and S-methylisothiourea [SMT]) were simultaneously administered in rats by a single intraarticular injection in each knee [33].
  • METHODS: Thirteen young healthy subjects finished an exhaustive bicycle exercise protocol while they were infused placebo or the NO-synthase inhibitor N-monomethyl-L-arginine (L-NMMA) on two separate days in a randomized, double blind cross-over design [34].
  • Cardiovascular effects were evaluated before and after microinjection of the HO inhibitor zinc deuteroporphyrin 2,4-bis glycol (ZnDPBG: 1 nmol) or the NO synthase (NOS) inhibitors N -monomethyl-l-arginine (l-NMMA: 10, 33 and 100 nmol) and N-nitro-l-arginine methyl ester (l-NAME: 10, 33 and 100 nmol) [35].
  • Carrageenan was injected into the plantar surface of the hind paw during perfusion of the dialysis catheter with modified Ringer's solution or N-monomethyl-L-arginine acetate [36].


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  19. Human NK cells express endothelial nitric oxide synthase, and nitric oxide protects them from activation-induced cell death by regulating expression of TNF-alpha. Furuke, K., Burd, P.R., Horvath-Arcidiacono, J.A., Hori, K., Mostowski, H., Bloom, E.T. J. Immunol. (1999) [Pubmed]
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  21. Ramipril dose-dependently increases nitric oxide availability in the radial artery of essential hypertension patients. Ghiadoni, L., Versari, D., Magagna, A., Kardasz, I., Plantinga, Y., Giannarelli, C., Taddei, S., Salvetti, A. J. Hypertens. (2007) [Pubmed]
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