Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H18N4O2 |
Molecular Weight | 202.2541 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=N)NCCC[C@H](N)C(O)=O
InChI
InChIKey=YDGMGEXADBMOMJ-LURJTMIESA-N
InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1
N, N – Dimethylarginine, more known as asymmetric dimethylarginine (ADMA), a naturally occurring chemical found in blood plasma. It is formed by methylation of arginine residues in proteins and released after proteolysis. ADMA is an endogenous inhibitor of all isoforms of nitric oxide synthase, the enzyme that synthesizes nitric oxide from arginine. Elevated plasma concentrations of ADMA are associated with hypertension and other risk factors for cardiovascular disease. It is known, that chronic kidney disease (CDK) is associated with increased risk of renal and cardiovascular events and it has been claimed that asymmetric dimethylarginine (ADMA) and symmetric dimethylarginine (SDMA), are contributing factors. Nevertheless, the recent comprehensive analysis of methylarginines in a cohort of patients with non-dialysis CKD have revealed, the potential pathophysiological role of SDMA in CKD progression and atherosclerotic cardiovascular disease among non-dialysis CKD patients. Thus SDMA predicts CKD progression and future atherosclerotic cardiovascular events more consistently than other methylarginines. In addition, was also shown, that the maternal plasma ADMA concentration is an important indicator of fetal growth restriction in women with impaired placental perfusion independent of NO.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096621 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16028689 |
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Target ID: CHEMBL2111405 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16028689 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension. | 1999 Apr |
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Plasma levels of asymmetrical dimethyl-L-arginine in patients with congenital heart disease and pulmonary hypertension. | 2001 Apr |
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Acute administration of L-arginine does not improve arterial endothelial function in chronic renal failure. | 2001 Dec |
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Leptin improves membrane fluidity of erythrocytes in humans via a nitric oxide-dependent mechanism--an electron paramagnetic resonance investigation. | 2002 Sep 27 |
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Plasma concentrations of nitric oxide and asymmetric dimethylarginine in human alcoholic cirrhosis. | 2004 Jul |
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A selective estrogen receptor modulator, tamoxifen, and membrane fluidity of erythrocytes in normotensive and hypertensive postmenopausal women: an electron paramagnetic resonance investigation. | 2005 Aug |
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Determination of methylated arginines by column-switching high-performance liquid chromatography-fluorescence detection. | 2005 Oct |
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Cross-talk between the kidney and the cardiovascular system. | 2006 Aug |
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High glucose-mediated imbalance of nitric oxide synthase and dimethylarginine dimethylaminohydrolase expression in endothelial cells. | 2006 Feb |
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Elevated plasma asymmetric dimethyl-L-arginine levels are linked to endothelial progenitor cell depletion and carotid atherosclerosis in rheumatoid arthritis. | 2007 Mar |
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A new selective pre-column ninhydrin-based derivatization for a RP-HPLC determination of plasma asymmetric dimethyl-L-arginine (ADMA) by fluorescence detection. | 2008 May |
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L-arginine analogs--inactive markers or active agents in atherogenesis? | 2008 Oct |
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Telmisartan decreases plasma levels of asymmetrical dimethyl-L-arginine and improves lipid and glucose metabolism and vascular function. | 2009 Jan |
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Advanced glycation end-products induce vascular dysfunction via resistance to nitric oxide and suppression of endothelial nitric oxide synthase. | 2010 Apr |
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The Role of Asymmetric Dimethylarginine (ADMA) in Endothelial Dysfunction and Cardiovascular Disease. | 2010 May |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26959555
Asymmetric dimethylarginine (N,N-DIMETHYLARGININE; ADMA) induces the mitochondrial translocation of endothelial nitric oxide synthase (eNOS) through the nitration-mediated activation of Akt1. The study was performed to elucidate the potential effect of ADMA on Akt1 phosphorylation and the mechanisms that are involved. Western blot analysis demonstrated that, although ADMA (10 μM, 2 h) does not change total Akt1 levels. Akt1 phosphorylation at T308 and S473 were significantly increased. It was also found that ADMA treatment significantly increased Akt1 translocation from cytosol to the plasma membrane, suggesting that upon ADMA stimulation, Akt1 was activated, at least in part, through recruitment to that plasma membrane.
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Classification Tree | Code System | Code | ||
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LOINC |
79635-9
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NCI_THESAURUS |
C73539
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LOINC |
74363-3
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LOINC |
80981-4
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C018524
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DTXSID401017725
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30315-93-6
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17929
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C124264
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63CV1GEK3Y
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DB01686
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123831
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ASYMMETRIC DIMETHYLARGININE
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PARENT (METABOLITE)
SUBSTANCE RECORD