Page last updated: 2024-11-08

symmetric dimethylarginine

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Description

N(omega),N'(omega)-dimethyl-L-arginine : A L-arginine derivative having two methyl groups at the N(omega)- and N'(omega)-positions [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID169148
CHEBI ID25682
SCHEMBL ID287988
SCHEMBL ID13484056
MeSH IDM0083681

Synonyms (53)

Synonym
HSCI1_000216
n(g1),n(g2)-dimethylarginine
(s)-2-amino-5-(n',n''-dimethylguanidino)pentanoic acid
n3,n4-dimethyl-l-arginine
symmetric dimethylarginine
ng,n'g-dimethylarginine
n3,n4-dimethylarginine
guanidino-n(1),n(2)-dimethylarginine
DB02302
n,n'-dimethylarginine
sdma
CHEBI:25682
(2s)-2-amino-5-(n',n''-dimethylcarbamimidamido)pentanoic acid
30344-00-4
n(3),n(4)-dimethylarginine
n(omega),n'(omega)-dimethyl-l-arginine
n(5)-(n,n'-dimethylcarbamimidoyl)-l-ornithine
2mr ,
n3, n4-dimethylarginine
(2s)-2-amino-5-[(n,n'-dimethylcarbamimidoyl)amino]pentanoic acid
49787g1ulv ,
unii-49787g1ulv
l-ornithine, n5-((methylamino)(methylimino)methyl)-
S5838
gtpl5271
(2s)-2-amino-5-[(e)-2,3-dimethylcarbamimidamido]pentanoic acid
SCHEMBL287988
(s)-2-amino-5-((bis(methylamino)methylene)amino)pentanoic acid
SCHEMBL13484056
l-ornithine, n5-[bis(methylamino)methylene]-
ng,n'g-dimethyl-l-arginine
omega-n,omega-n'-dimethyl-l-arginine
(2s)-2-amino-5-[(e)-1,2-dimethylcarbamimidamido]pentanoic acid
symmetric dimethyl-l-arginine
AKOS026674174
n5-[bis(methylamino)methylene]-l-ornithine
n5-((methylamino)(methylimino)methyl)-l-ornithine
ng,ng'-dimethylarginine
n5-(n,n'-dimethylamidino)-l-ornithine
HY-101410
CS-6304
n~5~-(n,n'-dimethylcarbamimidoyl)-l-ornithine
mfcd14705169
HVPFXCBJHIIJGS-LURJTMIESA-N
AS-47105
Q23759026
l-ornithine, n5-[(methylamino)(methylimino)methyl]-
ng,ng'-dimethyl-l-arginine
symmetric dimethylarginine; ng,ng'-dimethyl-l-arginine
DTXSID00952691
n~5~-(n,n'-dimethylcarbamimidoyl)ornithine
F12063
(s)-2-amino-5-((bis(methylamino)methylene)amino)pentanoicacid

Research Excerpts

Overview

Symmetric dimethylarginine (SDMA) is a renal biomarker correlated with glomerular filtration rate (GFR) It is incorporated into the International Renal Interest Society (IRIS) guidelines for diagnosing, staging, and treating chronic kidney disease.

ExcerptReferenceRelevance
"Symmetric dimethylarginine (SDMA) is a ubiquitous analyte that is freely filtered by the glomerulus and can be detected in serum."( Symmetric Dimethylarginine Is a Sensitive Biomarker of Glomerular Injury in Rats.
Biswas, S; Dunn, C; Himmel, L; Kohnken, R; LeRoy, B; Logan, M; Peterson, R, 2022
)
2.89
"Symmetric dimethylarginine (SDMA) is a renal biomarker correlated with glomerular filtration rate (GFR)."( Symmetric dimethylarginine concentrations in healthy neonatal foals and mares.
Bozorgmanesh, R; Coyne, M; Fletcher, C; Hegarty, E; Mack, R; Murphy, R; Slovis, N; Snyder, J; Thornton, J, 2021
)
3.51
"Symmetric dimethylarginine (SDMA) is an excretory renal function biomarker shown to correlate well with glomerular filtration rate in dogs, cats, humans, and rats. "( Evaluation of Renal Biomarkers, Including Symmetric Dimethylarginine, following Gentamicin-Induced Proximal Tubular Injury in the Rat.
Coyne, MJ; Cross, J; Drake, C; Hamlin, DM; Leissinger, MK; Mack, R; McCrann, DJ; Murphy, RE; Schultze, AE; Strong-Townsend, M; Yerramilli, M, 2022
)
2.43
"Symmetric dimethylarginine (SDMA) is a valuable surrogate marker for decreased glomerular filtration rate (GFR) and is incorporated into the International Renal Interest Society (IRIS) guidelines for diagnosing, staging, and treating chronic kidney disease (CKD). "( Symmetrical Dimethylarginine: Evaluating Chronic Kidney Disease in the Era of Multiple Kidney Biomarkers.
Clements, C; Mack, R; Michael, H; Szlosek, D, 2022
)
2.16
"Symmetric dimethylarginine (SDMA) is a serum biomarker of excretory renal function which consistently correlates with glomerular filtration rate (GFR) across multiple species including rats, dogs, and humans. "( Evaluation of renal injury and function biomarkers, including symmetric dimethylarginine (SDMA), in the rat passive Heymann nephritis (PHN) model.
Coyne, MJ; Cross, J; Drake, C; Mack, R; McCrann, DJ; Murphy, RE; Schultze, AE; Strong-Townsend, M, 2022
)
2.4
"Symmetric dimethylarginine (SDMA) is an independent cardiovascular risk factor in patients with chronic kidney diseases, which is mostly excreted through renal tubules."( SDMA attenuates renal tubulointerstitial fibrosis through inhibition of STAT4.
Chen, D; Huang, D; Lin, P; Tan, B; Wang, Y; Wu, M; Ye, C, 2023
)
1.63
"Symmetric dimethylarginine (SDMA) is a methylated arginine derived from intranuclear methylation of l-arginine by protein-arginine methyltransferase and released into circulation after proteolysis. "( Symmetric dimethylarginine concentrations in dogs with International Renal Interest Society stage 4 chronic kidney disease undergoing intermittent hemodialysis.
Coyne, M; Geraldes, SS; Guimarães-Okamoto, PTC; Le Sueur, ANV; Melchert, A; Murphy, R; Szlosek, D; Takahira, RK, 2019
)
3.4
"Asymmetric dimethylarginine (ADMA) acts as an inhibitor of eNOS."( Increased Serum Levels of Asymmetric Dimethylarginine and Symmetric Dimethylarginine and Decreased Levels of Arginine in Sudanese Patients with Essential Hypertension.
Abdalrahman, IBB; Bakheit, KH; Erdmann, J; Gamil, S; Mohamed, AO; Schwedhelm, E, 2020
)
1.48
"Symmetric dimethylarginine (SDMA) is a serum biomarker of renal damage in dogs. "( Symmetric dimethylarginine in dogs with myxomatous mitral valve disease at various stages of disease severity.
Contiero, B; Domenech, O; Guglielmini, C; Poser, H; Valente, C; Zini, E, 2020
)
3.44
"Asymmetric dimethylarginine (ADMA) is a cardiac biomarker in humans, symmetric dimethylarginine (SDMA) a renal biomarker in humans, cats, and dogs. "( Asymmetric dimethylarginine-A potential cardiac biomarker in horses.
Bollinger, L; Ertelt, A; Gehlen, H; Kuban, S; Liertz, S; Merle, R; Stumpff, F, 2021
)
2.44
"Symmetric dimethylarginine (SDMA) is a promising renal marker that correlates well with the glomerular filtration rate and could allow earlier detection of impaired renal function. "( Serum symmetric dimethylarginine shows a relatively consistent long-term concentration in healthy dogs with a significant effect of increased body fat percentage.
Broeckx, BJG; Daminet, S; Hesta, M; Hillaert, A; Liu, DJX; Paepe, D; Stock, E; Vanderperren, K, 2021
)
2.54
"Symmetric dimethylarginine (SDMA) is a sensitive surrogate marker for glomerular filtration rate; however, there are uncertainties as to how to interpret mild increases (SDMA 15-19 μg/dL). "( Longitudinal evaluation of symmetric dimethylarginine and concordance of kidney biomarkers in cats and dogs.
Grauer, GF; Hegarty, E; Mack, RM; McCrann, DJ; Michael, HT, 2021
)
2.36
"Symmetric dimethylarginine (SDMA) is an inactive stereoisomer of ADMA."( High asymmetric dimethylarginine, symmetric dimethylarginine and L-arginine levels in migraine patients.
Asil, T; Celik, Y; Gunduz, O; Karadag, H; Reyhani, A; Sut, N, 2017
)
1.66
"Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of nitric oxide synthases that limits nitric oxide bioavailability. "( Cardiomyocyte dimethylarginine dimethylaminohydrolase-1 (DDAH1) plays an important role in attenuating ventricular hypertrophy and dysfunction.
Atzler, D; Böger, RH; Chen, P; Chen, Y; Fassett, J; Guo, H; Hu, X; Kwak, D; Liu, X; Lu, Z; Schwedhelm, E; Wang, H; Xu, X; Yue, W; Zhang, P, 2017
)
1.37
"Symmetric dimethylarginine (SDMA) is a screening tool for early kidney dysfunction and monitoring treatment in cases of chronic kidney disease (CKD). "( Variability of Symmetric Dimethylarginine in Apparently Healthy Dogs.
Burchell, RK; Burton, SE; Gal, A; Kopke, MA; Lopez-Villalobos, N; Ruaux, CG, 2018
)
2.28
"Symmetric dimethylarginine (SDMA) is a renal biomarker in humans, dogs, and cats that correlates with serum creatinine and GFR and appears to be an earlier and more specific biomarker for kidney disease."( RETROSPECTIVE ANALYSIS AND VALIDATION OF SERUM SYMMETRIC DIMETHYLARGININE (SDMA) CONCENTRATIONS IN CHEETAHS ( ACINONYX JUBATUS).
Brandão, J; Cole, GA; Cross, J; D'Agostino, J; Hardy, S; Li, J; Lyon, S; Rakitin, A; Strong-Townsend, M; Waugh, L; Yerramilli, M, 2018
)
1.46
"Symmetric dimethylarginine (SDMA) is a novel kidney biomarker that reflects glomerular filtration rate, increasing earlier than sCr with acute kidney injury and chronic kidney disease."( Comparative performance of IDEXX SDMA Test and the DLD SDMA ELISA for the measurement of SDMA in canine and feline serum.
Clements, C; Coyne, M; Cross, J; Drake, C; Ernst, R; Friis, H; McCrann, D; Murphy, R; Ogeer, J; Strong-Townsend, M, 2018
)
1.2
"Asymmetric dimethylarginine (ADMA) is an endogenous nitric oxide synthase (NOS) inhibitor known as a mediator of endothelial dysfunction and atherosclerosis. "( ADMA/SDMA in elderly subjects with asymptomatic carotid atherosclerosis: values and site-specific association.
Bucciarelli, T; D'Orazio, N; Gallina, S; Riccioni, G; Scotti, L; Speranza, L; Speziale, G, 2014
)
1.31
"Symmetric dimethylarginine (SDMA) is an accurate and precise biomarker for estimating glomerular filtration rate (GFR) in humans and cats. "( Relationship between lean body mass and serum renal biomarkers in healthy dogs.
Hall, JA; Jewell, DE; Melendez, LD; Obare, E; Yerramilli, M,
)
1.57
"Symmetric dimethylarginine (SDMA) is a small molecule formed by methylation of arginine, and released into blood during protein degradation. "( Symmetric Dimethylarginine Assay Validation, Stability, and Evaluation as a Marker for the Early Detection of Chronic Kidney Disease in Dogs.
Aguiar, J; Boggess, MM; Lees, GE; Nabity, MB; Obare, E; Rakitin, A; Relford, R; Yerramilli, M,
)
3.02
"Symmetric dimethylarginine (SDMA) is a catabolic product of arginine-methylated proteins and is an emerging biomarker for kidney function. "( Comparison of symmetric dimethylarginine with creatinine, cystatin C and their eGFR equations as markers of kidney function.
Bunch, DR; El-Khoury, JM; Hu, B; Payto, D; Reineks, EZ; Wang, S, 2016
)
2.24
"Symmetric dimethylarginine (SDMA) is a sensitive circulating kidney biomarker whose concentrations increase earlier than creatinine as glomerular filtration rate decreases."( Symmetric Dimethylarginine: Improving the Diagnosis and Staging of Chronic Kidney Disease in Small Animals.
Clements, C; Relford, R; Robertson, J, 2016
)
2.6
"Asymmetric dimethylarginine (ADMA) that is an endogenous inhibitor of NO synthesis may impair the effective coronary collateral vessel development."( Asymmetric dimethylarginine and coronary collateral vessel development.
Akyel, A; Biberoglu, G; Cengel, A; Hasanoglu, A; Kocaman, SA; Sahinarslan, A; Timurkaynak, T, 2008
)
1.88
"Asymmetric dimethylarginine (ADMA) is a product of protein hydrolysis and an endogenous competitive inhibitor of nitric oxide synthase. "( Asymmetric dimethylarginine in hematological malignancies: a preliminary study.
Andrzejak, R; Antonowicz-Juchniewicz, J; Chachaj, A; Dzietczenia, J; Kuliczkowski, K; Mazur, G; Szuba, A; Wróbel, T, 2008
)
2.17
"Asymmetric dimethylarginine (ADMA) is an endogenous modulator of endothelial function and oxidative stress, and increased levels of this molecule have been reported in some metabolic disorders and cardiovascular diseases. "( Time course of asymmetric dimethylarginine (ADMA) and oxidative stress in fructose-hypertensive rats: a model related to metabolic syndrome.
Collin, B; Cottin, Y; Duvillard, L; Goirand, F; Guilland, JC; Korandji, C; Lauzier, B; Moreau, D; Rochette, L; Sicard, P; Vergely, C; Zeller, M, 2011
)
1.63
"Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of nitric oxide (NO) synthesis causing endothelial dysfunction, an early sign of atherogenesis. "( Asymmetric dimethylarginine as an independent risk marker for mortality in ambulatory patients with peripheral arterial disease.
Atzler, D; Benndorf, RA; Böger, RH; Darius, H; Diehm, C; Endres, HG; Lüneburg, N; Maas, R; Schwedhelm, E; Thiem, U; von Stritzky, B, 2011
)
2.19
"Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of nitric oxide synthases. "( The role of asymmetric and symmetric dimethylarginines in renal disease.
Böger, RH; Schwedhelm, E, 2011
)
1.58
"Symmetric dimethylarginine (SDMA) is a stereoisomer produced alongside ADMA, and has recently been described as a risk factor for cardiovascular events."( Symmetric dimethylarginine (SDMA) is raised in women with polycystic ovary syndrome: a pilot study.
Barry, JA; Hardiman, PJ; Kay, AR; Lakhani, K; Leiper, J, 2011
)
2.53
"Asymmetric dimethylarginine (ADMA) is an endogenous nitric oxide synthase (NOS) inhibitor that competes with L-arginine for binding to NOS. "( Asymmetric dimethylarginine is increased in asthma.
Belik, J; Grasemann, H; Huang, H; North, ML; Pencharz, P; Rafii, M; Scott, JA; Subbarao, P, 2011
)
2.19
"Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of nitric oxide (NO) which plays an important role in controlling vascular tone and regulates the contractile properties of cardiac myocytes. "( The biological effect of pharmacological treatment on dimethylaminohydrolases (DDAH-1) and cationic amino acid transporter-1 (CAT-1) expression in patients with acute congestive heart failure.
Bucciarelli, T; D'Orazio, N; Felaco, M; Franceschelli, S; Gaeta, R; Grilli, A; Riccioni, G; Speranza, L, 2011
)
1.28
"Symmetric dimethylarginine (SDMA) is a by-product of protein methylation. "( Plasma symmetric dimethylarginine reference limits from the Framingham offspring cohort.
Atzler, D; Böger, RH; Glazer, NL; Lüneburg, N; Maas, R; Riederer, U; Schwedhelm, E; Sullivan, LM; Vasan, RS; Xanthakis, V, 2011
)
2.27
"Symmetric dimethylarginine (SDMA) seems to be a good marker of multiorgan failure, especially renal failure."( Diagnostic value of plasma asymmetric and symmetric dimethylarginine levels in liver transplant recipients.
Kokot, F; Kunsdorf-Wnuk, A; Wnuk, Z, 2012
)
1.36
"Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of nitric oxide (NO) synthase. "( Estradiol, acting through estrogen receptor alpha, restores dimethylarginine dimethylaminohydrolase activity and nitric oxide production in oxLDL-treated human arterial endothelial cells.
Bueno-Betí, C; Hermenegildo, C; Laguna-Fernández, A; Lázaro-Franco, M; Monsalve, E; Novella, S; Sanchís, J; Sobrino, A; Tarín, JJ, 2013
)
1.3
"Asymmetric dimethylarginine (ADMA) is an endogenous nitric oxide synthase inhibitor, which has been associated with total and cardiovascular mortality in various clinical settings. "( Asymmetric and symmetric dimethylarginine and risk of secondary cardiovascular disease events and mortality in patients with stable coronary heart disease: the KAROLA follow-up study.
Böger, R; Breitling, LP; Brenner, H; Koenig, W; Maas, R; Rothenbacher, D; Schwedhelm, E; Siegerink, B; Vossen, CY, 2013
)
1.65
"Asymmetric dimethylarginine (ADMA) is an emerging cardiovascular risk factor. "( High-performance liquid chromatographic assay of asymmetric dimethylarginine, symmetric dimethylarginine, and arginine in human plasma by derivatization with naphthalene-2,3-dicarboxaldehyde.
Bonfigli, AR; Coppa, G; Gambini, A; Marra, M; Testa, I; Testa, R, 2003
)
1.48
"Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of endothelial nitric oxide and plasma level of ADMA is often elevated in HH."( Asymmetric dimethylarginine is not elevated in exfoliation syndrome but symmetric dimethylarginine is related to exfoliative glaucoma.
Blomster, H; Kontkanen, M; Puustjärvi, T; Teräsvirta, M; Uusitalo, H; Valtonen, P, 2007
)
1.87
"Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of nitric oxide production. "( Health-associated reference values for arginine, asymmetric dimethylarginine (ADMA) and symmetric dimethylarginine (SDMA) measured with high-performance liquid chromatography.
Asberg, A; Bigonah, A; Hov, GG; Sagen, E, 2007
)
1.5
"Asymmetric dimethylarginine (ADMA) is an endogenous and competitive inhibitor of nitric oxide synthase. "( Does ADMA cause endothelial dysfunction?
Cooke, JP, 2000
)
1.22

Effects

Symmetric dimethylarginine (SDMA) has been increasingly used as a marker of early chronic kidney disease (CKD) in cats. Little is known about the influence of comorbidities on SDMA in this species.

ExcerptReferenceRelevance
"Symmetric dimethylarginine (SDMA) has been shown to increase earlier than creatinine in cats with renal dysfunction, and, unlike creatinine, SDMA is not impacted by lean muscle mass."( A retrospective evaluation of the relationship between symmetric dimethylarginine, creatinine and body weight in hyperthyroid cats.
Clements, C; Coyne, MJ; Mack, R; McCrann, DJ; Ogeer, J; Quimby, J; Robertson, J; Szlosek, D, 2020
)
1.53
"Symmetric dimethylarginine (SDMA) has been shown to be a valuable biomarker for early detection of chronic kidney disease (CKD) in canine and feline patients. "( EVALUATION OF SYMMETRIC DIMETHYLARGININE AS AN EARLY BIOMARKER OF CHRONIC KIDNEY DISEASE IN CAPTIVE CHEETAHS (ACINONYX JUBATUS).
Lamglait, B; Vandenbunder-Beltrame, M, 2017
)
2.26
"Symmetric dimethylarginine (SDMA) has been increasingly used as a marker of early chronic kidney disease (CKD) in cats, but little is known about the influence of comorbidities on SDMA in this species."( Symmetric Dimethylarginine in Cats with Hypertrophic Cardiomyopathy and Diabetes Mellitus.
Christiansen, LB; Jessen, LR; Kieler, IN; Koch, J; Langhorn, R, 2018
)
3.37
"Symmetric dimethylarginine (SDMA) has limited studies in cats with changing thyroid status."( Changes in thyroid and renal function after bilateral thyroidectomy in cats.
Chang, YM; Covey, HL; Elliott, J; Syme, HM, 2019
)
1.24
"Symmetric dimethylarginine (SDMA) has been shown to be an accurate and precise biomarker for calculating estimated glomerular filtration rate (GFR) in humans, as well as a more sensitive biomarker than serum creatinine concentration (sCr) for assessing renal dysfunction."( Comparison of serum concentrations of symmetric dimethylarginine and creatinine as kidney function biomarkers in cats with chronic kidney disease.
Hall, JA; Jewell, DE; Obare, E; Yerramilli, M,
)
1.85
"Asymmetric dimethylarginine (ADMA) has been implicated in the prognosis after acute myocardial infarction (AMI) and heart failure (HF)."( Increased Symmetric Dimethylarginine Level Is Associated with Worse Hospital Outcomes through Altered Left Ventricular Ejection Fraction in Patients with Acute Myocardial Infarction.
Cottin, Y; Guenancia, C; Guilland, JC; Lorin, J; Rochette, L; Stamboul, K; Vergely, C; Zeller, M, 2017
)
1.77
"Asymmetric dimethylarginine (ADMA) has raised considerable interest, as it is an endogenous inhibitor of nitric oxide synthesis. "( Asymmetric and symmetric dimethylarginines are of similar predictive value for cardiovascular risk in the general population.
Egger, G; Holt, DW; Kiechl, S; Lee, T; Mayr, M; Santer, P; Thompson, G; Tsimikas, S; Willeit, J; Xu, Q, 2009
)
1.62
"Asymmetric dimethylarginine (ADMA) has been suggested as a possible marker of endothelial dysfunction, and interest in its use in clinical practice is increasing. "( HPLC determination of plasma dimethylarginines: method validation and preliminary clinical application.
Artusi, C; Boffa, GM; Ivanova, M; Plebani, M; Zaninotto, M, 2010
)
1.27
"Asymmetric dimethylarginine (ADMA) has been reported to affect the synthesis of nitric oxide (NO) in endothelial cells by inhibiting endothelial NO synthase (eNOS) activity and to cause endothelial dysfunction in humans. "( Nebivolol reduces asymmetric dimethylarginine in endothelial cells by increasing dimethylarginine dimethylaminohydrolase 2 (DDAH2) expression and activity.
Boccioletti, V; Cominacini, L; Garbin, U; Manfro, S; Pasini, AF; Stranieri, C, 2007
)
1.58

Actions

ExcerptReferenceRelevance
"Symmetric dimethylarginine was lower (P < .01) in Percherons and Belgians, than in Clydesdales."( Symmetric dimethylarginine and creatinine concentrations in serum of healthy draft horses.
Coyne, M; Cross, J; Gallant, LR; Li, J; Murphy, R; Schott, HC; Strong-Townsend, M; Szlosek, D; Yerramilli, M, 2021
)
2.79

Compound-Compound Interactions

ExcerptReferenceRelevance
"001) or in combination with L-arginine (9."( Asymmetric dimethylarginine determines the improvement of endothelium-dependent vasodilation by simvastatin: Effect of combination with oral L-arginine.
Benndorf, RA; Bierend, A; Böger, GI; Böger, RH; Dumbadze, E; Maas, R; Rudolph, TK; Schwedhelm, E, 2007
)
1.25

Bioavailability

ExcerptReferenceRelevance
"Chronic kidney disease (CKD) and hypertension have been associated with decreased bioavailability of nitric oxide (NO) and endothelial dysfunction."( Plasma asymmetric dimethylarginine, symmetric dimethylarginine, l-arginine, and nitrite/nitrate concentrations in cats with chronic kidney disease and hypertension.
Elliott, J; Jepson, RE; Syme, HM; Vallance, C,
)
0.57
" In conclusion, an unfavourable NOS substrate/inhibitor ratio may contribute to the reduced NO bioavailability associated with inflammation."( Systemic inflammation is linked to low arginine and high ADMA plasma levels resulting in an unfavourable NOS substrate-to-inhibitor ratio: the Hoorn Study.
Dekker, JM; Heine, RJ; Scheffer, PG; Stehouwer, CD; Teerlink, T; van der Zwan, LP, 2011
)
0.37
" The higher ADMA level after cesarean birth compared with vaginal birth may contribute to decreased nitric oxide production and bioavailability in neonatal vascular beds."( Birth by cesarean section is associated with elevated neonatal plasma levels of dimethylarginines.
Bode-Böger, SM; Ertl, T; Martens-Lobenhoffer, J; Sulyok, E; Vida, G, 2012
)
0.38
"In hyperhomocysteinemia (HHcy), an independent risk factor for cardiovascular diseases, endothelial dysfunction due to reduced bioavailability of nitric oxide is a consistent finding."( Asymmetric dimethylarginine in adults with cystathionine β-synthase deficiency.
Blom, HJ; Castro, R; Jakobs, C; Janssen, MC; Kluijtmans, LA; Rivera, I; Rocha, MS; Smulders, Y; Tavares de Almeida, I; Teerlink, T, 2012
)
1.29
" Increased oxidative stress impairs NO bioavailability and has been described in plasma of coronary artery disease (CAD) patients."( Nitric oxide synthetic pathway in red blood cells is impaired in coronary artery disease.
Cavalca, V; Chiorino, E; Crisci, M; Eligini, S; Garlaschè, A; Giovannardi, M; Lualdi, A; Porro, B; Squellerio, I; Tremoli, E; Veglia, F; Werba, JP, 2013
)
0.39
" Nebivolol increases the bioavailability of NO."( Digital plethysmography and arginine metabolism in prehypertension: effect of nebivolol therapy.
Delafontaine, P; Egan, P; Fernandez, C; Giles, TD; Kandavar, R; Kim, C; Roffidal, LE; Sander, GE; Sukhanov, S; Velaga, S, 2015
)
0.42
"Pathways of oxidative stress, nitric oxide bioavailability and L-arginine derivatives are hypothesized to be related to atrial fibrillation (AF)."( ADMA, subclinical changes and atrial fibrillation in the general population.
Appelbaum, S; Atzler, D; Bauer, C; Blankenberg, S; Böger, RH; Hoffmann, B; Lackner, KJ; Münzel, T; Ojeda, FM; Ramuschkat, M; Schnabel, RB; Schwedhelm, E; Sinning, CR; Wild, PS; Zeller, T, 2016
)
0.43
"In 71 in-patients with major depression and 48 healthy controls the Global Arginine Bioavailability Ratio (GABR), arginase activity (arginine/ornithine ratio), the L-arginine/ADMA ratio, ADMA, and SDMA were determined by high-pressure liquid chromatography."( Nitric Oxide-Related Biological Pathways in Patients with Major Depression.
Amouzadeh-Ghadikolai, O; Baranyi, A; Baranyi, M; Hlade, P; Koppitz, M; Meinitzer, A; Reicht, G; Robier, C; Rothenhäusler, HB; Theokas, S, 2015
)
0.42
" In addition, after a first improvement of depression at the time of hospital discharge, a significant decrease in arginase activity, an increased L-arginine/ADMA ratio and a trend for increased global arginine bioavailability were observed."( Nitric Oxide-Related Biological Pathways in Patients with Major Depression.
Amouzadeh-Ghadikolai, O; Baranyi, A; Baranyi, M; Hlade, P; Koppitz, M; Meinitzer, A; Reicht, G; Robier, C; Rothenhäusler, HB; Theokas, S, 2015
)
0.42
" Test food contained functional lipids (fish oil), antioxidants (vitamins C and E), L-carnitine, botanicals (vegetables), highly bioavailable protein, and amino acid supplements."( Positive Impact of Nutritional Interventions on Serum Symmetric Dimethylarginine and Creatinine Concentrations in Client-Owned Geriatric Cats.
Hall, JA; Jewell, DE; MacLeay, J; Obare, E; Paetau-Robinson, I; Schiefelbein, H; Yerramilli, M, 2016
)
0.68
" Test food contained functional lipids (fish oil), antioxidants (lipoic acid, vitamins C and E), L-carnitine, botanicals (fruits and vegetables), controlled sodium concentration, and high quality protein sources (high bioavailability and an ideal amino acid composition)."( Positive Impact of Nutritional Interventions on Serum Symmetric Dimethylarginine and Creatinine Concentrations in Client-Owned Geriatric Dogs.
Hall, JA; Jewell, DE; MacLeay, J; Obare, E; Paetau-Robinson, I; Schiefelbein, H; Yerramilli, M, 2016
)
0.68
", the global arginine bioavailability ratio (GABR) and related serum amino acids, between MDD patients and non-depressed controls, and between remitted and non-remitted MDD patients."( Global arginine bioavailability ratio is decreased in patients with major depressive disorder.
Ali-Sisto, T; Honkalampi, K; Koivumaa-Honkanen, H; Lehto, SM; Mäntyselkä, P; Nandania, J; Ruusunen, A; Tolmunen, T; Valkonen-Korhonen, M; Velagapudi, V; Viinamäki, H, 2018
)
0.48
"Arginine bioavailability may be decreased in MDD."( Global arginine bioavailability ratio is decreased in patients with major depressive disorder.
Ali-Sisto, T; Honkalampi, K; Koivumaa-Honkanen, H; Lehto, SM; Mäntyselkä, P; Nandania, J; Ruusunen, A; Tolmunen, T; Valkonen-Korhonen, M; Velagapudi, V; Viinamäki, H, 2018
)
0.48
" These data define a role for dysregulation of NO biosynthetic pathways in the pathogenesis of MIP and support the evaluation of interventions to enhance l-arginine bioavailability as strategies to improve birth outcomes."( Malaria in pregnancy alters l-arginine bioavailability and placental vascular development.
Cahill, LS; Conroy, AL; Elphinstone, R; Gamble, JL; Gazdzinski, LM; Kain, KC; Kalilani-Phiri, L; Madanitsa, M; McDonald, CR; Mwapasa, V; Philson, AC; Sled, JG; Ter Kuile, FO; Zhong, KJY, 2018
)
0.48
"Global L-arginine bioavailability was diminished, whereas plasma arginase activity, ADMA, and SDMA levels were elevated, in patients with RA compared with healthy control subjects."( Elevated levels of plasma symmetric dimethylarginine and increased arginase activity as potential indicators of cardiovascular comorbidity in rheumatoid arthritis.
Chandrasekharan, UM; Elaine Husni, M; Hazen, SL; Wang, S; Wang, Z; Wilson Tang, WH; Wu, Y, 2018
)
0.78
" We conclude that arginine bioavailability is important in T2D pathophysiology."( Changes in arginine are inversely associated with type 2 diabetes: A case-cohort study in the PREDIMED trial.
Arós, F; Bullo, M; Clish, C; Cofán, M; Corella, D; Dennis, C; Estruch, R; Fitó, M; Guasch-Ferré, M; Gutiérrez-Bedmar, M; Hu, FB; Lapetra, J; Liang, L; Martínez-González, MA; Papandreou, C; Razquin, C; Romaguera, D; Ros, E; Ruiz-Canela, M; Salas-Salvadó, J; Serra-Majem, L; Sorlí, JV; Toledo, E; Wang, DD; Yu, E, 2019
)
0.51
" Hence they affect production and bioavailability of eNOS-derived nitric oxide (NO) and consequently healthy blood vessels."( AGXT2 and DDAH-1 genetic variants are highly correlated with serum ADMA and SDMA levels and with incidence of coronary artery disease in Egyptians.
Abdel Rahman, MF; Amir, M; Gad, MZ; Hassanein, SI, 2018
)
0.48
" Wound character seems to affect NO bioavailability and wound etiology-arginine bioavailability."( Metabolites of the Nitric Oxide (NO) Pathway Are Altered and Indicative of Reduced NO and Arginine Bioavailability in Patients with Cardiometabolic Diseases Complicated with Chronic Wounds of Lower Extremities: Targeted Metabolomics Approach (LC-MS/MS).
Bednarz-Misa, I; Bronowicka-Szydełko, A; Fleszar, MG; Gacka, M; Gamian, A; Kędzior, K; Krzystek-Korpacka, M; Masłowski, L; Wiśniewski, J; Witkiewicz, W, 2019
)
0.51
" Impaired bioavailability of the nitric oxide precursor molecule L-arginine and higher concentrations of methylarginines (endogenous inhibitors of nitric oxide synthesis) are known to impair nitric oxide synthesis in numerous gastrointestinal cell types."( Serum L-arginine and endogenous methylarginine concentrations predict irritable bowel syndrome in adults: A nested case-control study.
Attia, JR; Hancock, SJ; Holliday, E; Mangoni, AA; McEvoy, MA; Oldmeadow, C; Peel, R; Smith, WT; Talley, NJ; Walker, MM, 2021
)
0.62
" Increased plasma ADMA has been widely recognized as a "trigger" initiating impaired NO bioavailability and vascular dysfunction, which ultimately leads to oxidative stress."( Asymmetric and symmetric dimethylarginine gingival crevicular fluid levels in periodontitis.
Güney, Z; Günhan, M; Kurgan, S; Mammadov, C; Önder, C; Serdar, MA, 2023
)
1.26

Dosage Studied

ExcerptRelevanceReference
" Dose-response relations were assessed by restricted cubic spline regression models and potential non-linearity was evaluated using a likelihood ratio test."( Asymmetric and Symmetric Dimethylarginine as Risk Markers for Total Mortality and Cardiovascular Outcomes: A Systematic Review and Meta-Analysis of Prospective Studies.
Lieb, W; Maas, R; Schlesinger, S; Sonntag, SR, 2016
)
0.79
" Rats were randomly assigned to one of three dose levels of gentamicin (20, 50, or 100 mg/kg) or a vehicle control group and dosed once daily by subcutaneous injection for either four or ten days."( Evaluation of Renal Biomarkers, Including Symmetric Dimethylarginine, following Gentamicin-Induced Proximal Tubular Injury in the Rat.
Coyne, MJ; Cross, J; Drake, C; Hamlin, DM; Leissinger, MK; Mack, R; McCrann, DJ; Murphy, RE; Schultze, AE; Strong-Townsend, M; Yerramilli, M, 2022
)
0.99
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
EC 1.14.13.39 (nitric oxide synthase) inhibitorAn EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
guanidinesAny organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
L-arginine derivativeA proteinogenic amino acid derivative resulting from reaction of L-arginine at the amino group, the carboxy group, or the guanidyl group, or from the replacement of any hydrogen of L-arginine by a heteroatom.
dimethylarginineAn arginine derivative that is arginine substituted by two methyl groups. A "closed" class.
amino acid zwitterionThe zwitterionic form of an amino acid having a negatively charged carboxyl group and a positively charged amino group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
eNOS activation and regulation1326
Nitric oxide metabolism in cystic fibrosis06

Research

Studies (408)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (0.98)18.7374
1990's4 (0.98)18.2507
2000's72 (17.65)29.6817
2010's239 (58.58)24.3611
2020's89 (21.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 48.84

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index48.84 (24.57)
Research Supply Index6.12 (2.92)
Research Growth Index5.87 (4.65)
Search Engine Demand Index74.48 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (48.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials27 (6.31%)5.53%
Reviews29 (6.78%)6.00%
Case Studies3 (0.70%)4.05%
Observational13 (3.04%)0.25%
Other356 (83.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]