Page last updated: 2024-12-04

glycocyamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Occurs in Manufacturing Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

glycocyamine: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

guanidinoacetate : A monocarboxylic acid anion that is the conjugate base of guanidinoacetic acid, obtained by deprotonation of the carboxy group. [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]

guanidinoacetic acid : The N-amidino derivative of glycine. [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 CID763
CHEMBL ID281593
CHEBI ID16344
SCHEMBL ID33970
MeSH IDM0046186

Synonyms (99)

Synonym
2-carbamimidamido-acetic acid
.alpha.-guanidinoacetic acid
acetic acid, [(aminoiminomethyl)amino]-
guanidine, (carboxymethyl)-
betacyamine
guanidylacetic acid
nsc1901 ,
guanidineacetic acid
guanyl glycine
glykocyamin
nsc-1901
glycine, n-(aminoiminomethyl)-
betasyamine
glycine, n-amidino-
n-(carbamimidoyl)glycine
CHEBI:16344 ,
n-carbamimidoylglycine
n-[amino(imino)methyl]glycine
(carbamimidamido)acetic acid
nsc26360
nsc-26360
nsc227847
nsc-227847
2-guanidinoacetic acid
guanidino acetate
NMG ,
guanidinoacetic acid
guanidinoacetate
C00581
352-97-6
guanidoacetic acid
n-amidinoglycine
GUANIDOACETIC_ACID ,
glycocyamine
guanidineacetic acid, 99%
amidinoglycine
n-(aminoiminomethyl)glycine
DB02751
nsc 1901
acetic acid, ((aminoiminomethyl)amino)-
ai3-17119
einecs 206-529-5
CHEMBL281593 ,
BMSE000384
n-guanylglycine
glycine, n-amidino- (8ci)
FT-0669070
G0167
n-amidino-glycine
bdbm50021601
AKOS005363765
STL164350
unii-go52o1a04e
go52o1a04e ,
FT-0626779
glycocyamine [mi]
amidinoglycine [inci]
glycocyamine [who-dd]
2-((amino(imino)methyl)amino)acetic acid
S6340
gtpl5325
n-(aminoiminomethyl)-glycine
SCHEMBL33970
guanidine acetic acid
(diaminomethylenamino)-essigsaure
W-106678
glucocyamine
([amino(imino)methyl]amino)acetic acid #
HMS3604I10
2-carbamimidamidoacetic acid
a-guanidinoacetic acid
b-guanidinoacetate
alpha-guanidinoacetic acid
a-guanidinoacetate
guanidoacetate
[(aminoiminomethyl)amino]-acetate
2-[[amino(imino)methyl]amino]acetic acid
alpha-guanidinoacetate
beta-guanidinoacetate
guanidylacetate
b-guanidinoacetic acid
(carboxymethyl)-guanidine
beta-guanidinoacetic acid
2-[[amino(imino)methyl]amino]acetate
[(aminoiminomethyl)amino]-acetic acid
HY-W021448
CS-0040590
mfcd00004278
SY015122
2-{[amino(imino)methyl]amino}acetic acid
AS-10760
DTXSID50861885
AC2229
Q2740979
gaa; glycocyamine; guanidinoacetate
2-[(diaminomethylidene)amino]acetic acid
EN300-49151
guanidineacetic--d2 acid
Z586248684

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The present study evaluated the effects of orally administered GAA on serum and urinary GAA, creatine and creatinine concentration, and on the occurrence of adverse events in healthy humans."( Creatine metabolism and safety profiles after six-week oral guanidinoacetic acid administration in healthy humans.
Niess, B; Obrenovic, M; Ostojic, SM; Stojanovic, M, 2013
)
0.39

Pharmacokinetics

ExcerptReferenceRelevance
"Guanidinoacetic acid (GAA), the natural precursor of creatine, has potential as a dietary supplement for human nutrition, yet no data are available regarding its dose-dependent pharmacokinetic (PK) behavior."( Single-dose oral guanidinoacetic acid exhibits dose-dependent pharmacokinetics in healthy volunteers.
Ostojic, SM; Vojvodic-Ostojic, A, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
" AGAT patients might benefit from oral GAA due to upgraded bioavailability and convenient utilization of the compound, while possible drawbacks (e."( Benefits and drawbacks of guanidinoacetic acid as a possible treatment to replenish cerebral creatine in AGAT deficiency.
Ostojic, SM, 2019
)
0.51
"The biosynthesis of creatine (Cr) is closely related to the bioavailability of guanidinoacetate (GAA)."( Hydrophilic interaction chromatography coupled to tandem mass spectrometry as a method for simultaneous determination of guanidinoacetate and creatine.
Gadžurić, S; Jovanov, P; Marić, A; Ostojić, S; Panić, J; Sakač, M; Vraneš, M, 2018
)
0.48
"This study assessed the relative bioavailability of guanidinoacetic acid (GAA) in cattle."( Relative bioavailability of guanidinoacetic acid delivered ruminally or abomasally to cattle.
Pearl, KA; Speer, HF; Titgemeyer, EC, 2020
)
0.56

Dosage Studied

ExcerptRelevanceReference
" In the healthy individuals, urinary guanidinoacetic acid excretion increased 5-fold by 2 h after dosing (15."( Clinical test of renal guanidinoacetic acid metabolism by oral citrulline and creatine loading.
Kadono, K; Tetsutani, T; Yamaguchi, T; Yasunaga, K, 1992
)
0.28
" The fact that the concentrations of neither GAA nor Arg changed significantly after the injection of 14C-Arg in either group suggested that the dosage of injected Arg is not sufficient to affect the transformation of Arg to GAA."( Study on impaired metabolism of guanidinoacetic acid in chronic renal failure rabbits with special reference to impaired conversion of arginine to guanidinoacetic acid.
Kuroda, M, 1993
)
0.29
" For this purpose, 16 healthy young volunteers were randomly divided to ingest in a double-blind fashion either creatine monohydrate or placebo (maltodextrine) at a dosage of 20 g/day for the first week (loading phase) and 5 g/day for 19 subsequent wk (maintenance phase)."( Plasma guanidino compounds are altered by oral creatine supplementation in healthy humans.
De Deyn, PP; Derave, W; Eijnde, BO; Hespel, P; Marescau, B; Vanden Eede, E, 2004
)
0.32
"Guanidinoacetic acid (GAA) is an intermediate in the biosynthesis of creatine (Cr), yet its use in human nutrition is limited due to a lack of a clear understanding of its' dose-response effect."( Dose-response effects of oral guanidinoacetic acid on serum creatine, homocysteine and B vitamins levels.
Drid, P; Hoffman, JR; Ostojic, SM; Stojanovic, M, 2014
)
0.4
"5 μmol/L on average at post-administration, yet no dose-response differences were found between trials."( Dose-response effects of oral guanidinoacetic acid on serum creatine, homocysteine and B vitamins levels.
Drid, P; Hoffman, JR; Ostojic, SM; Stojanovic, M, 2014
)
0.4
" The volume of distribution was affected by the dosage of GAA applied (102."( Single-dose oral guanidinoacetic acid exhibits dose-dependent pharmacokinetics in healthy volunteers.
Ostojic, SM; Vojvodic-Ostojic, A, 2015
)
0.42
" No dose-response differences were found between trials."( Six-Week Oral Guanidinoacetic Acid Administration Improves Muscular Performance in Healthy Volunteers.
Hoffman, JR; Ostojic, SM; Stojanovic, MD, 2015
)
0.42
"Volunteers were supplemented daily with 36 mg/kg body weight (BW) of GAA for the first 4 wk of the intervention; afterward GAA dosage was titrated ≤60 mg/kg BW of GAA daily."( Dietary guanidinoacetic acid increases brain creatine levels in healthy men.
Drid, P; Jovanov, P; Ostojic, J; Ostojic, SM; Vranes, M, 2017
)
0.46
" A calibration curve was built based on dose-response association using NutriTech data."( Estimation of Chicken Intake by Adults Using Metabolomics-Derived Markers.
Brennan, L; Flynn, A; Frost, G; Gibbons, H; Gibney, MJ; McNulty, BA; Nugent, AP; Rundle, M; Walton, J; Yin, X, 2017
)
0.46
" Taking all parameters into account, daily supplementation of 1300-1450 mg of GAA/kg diet was estimated as an optimum dosage maximizing the evaluated traits."( Dietary Guanidinoacetic acid modulates testicular histology and expression of c-Kit and STRA8 genes in roosters.
Ansari, M; Deldar, H; Nasirikhah, A; Sadeghi, M; Shakeri, M; Yousefi, AR; Zhandi, M, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Occurs in Manufacturing (2 Product(s))

Product Categories

Product CategoryProducts
Other1
Vitamins & Supplements1

Products

ProductBrandCategoryCompounds Matched from IngredientsDate Retrieved
Aurora NutraScience Active-Liposomal Creatine + GAA & R-ALA Drink Mix -- 30 PacketsAurora NutraScienceVitamins & SupplementsR-Alpha-Lipoic Acid, Guanidinoacetic Acid2024-11-29 10:47:42

Roles (5)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
nutraceuticalA product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
rat metaboliteAny mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
[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 (2)

ClassDescription
zwitterionA neutral compound having formal unit electrical charges of opposite sign on non-adjacent atoms. Sometimes referred to as inner salts, dipolar ions (a misnomer).
guanidinoacetic acids
[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 (11)

PathwayProteinsCompounds
Metabolism14961108
Amino acid and derivative metabolism250260
Creatine metabolism615
Arginine and Proline metabolism ( Arginine and Proline metabolism )4255
L-Arginine + Glycine = L-Ornithine + Guanidino-acetic acid ( Glycine and Serine metabolism )14
Glycine and Serine metabolism ( Glycine and Serine metabolism )3649
Creatine pathway116
Metabolic Epileptic Disorders2589
Biochemical pathways: part I0466
Amino acid metabolism094
Urea cycle and metabolism of amino groups2116

Protein Targets (17)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.505710.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.497310.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.498810.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.504610.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.506510.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.505710.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
GABA theta subunitRattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)IC50 (µMol)2.10000.00010.507510.0000AID72319
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
monoatomic ion transportProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid transportProton-coupled amino acid transporter 1Homo sapiens (human)
taurine transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
proline transportProton-coupled amino acid transporter 1Homo sapiens (human)
alanine transportProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid import across plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
glycine transportProton-coupled amino acid transporter 1Homo sapiens (human)
proline transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
proton transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
L-alanine transportProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
amino acid:proton symporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
proline:proton symporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
taurine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
protein bindingProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
alanine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
L-alanine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
L-proline transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
glycine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
lysosomal membraneProton-coupled amino acid transporter 1Homo sapiens (human)
endoplasmic reticulumProton-coupled amino acid transporter 1Homo sapiens (human)
plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
apical plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
vacuolar membraneProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID72319Inhibition of [3H]GABA binding to Gamma-aminobutyric acid A (GABA-A) receptor of rat brain membranes1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and structure-activity relationships of a series of aminopyridazine derivatives of gamma-aminobutyric acid acting as selective GABA-A antagonists.
AID94679In vivo blood glucose was determined in obese, hyperglycemic, hyperinsulinemic, insulin-resistant KKAy mice after a dose of 500 mg/kg for 4 days2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID630741Inhibition of human PAT1-mediated L-[3H]proline uptake in human Caco2 cells after 10 mins by liquid scintillation counting2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1).
AID94678In vivo blood glucose was determined in obese, hyperglycemic, hyperinsulinemic, insulin-resistant KKAy mice after a dose of 500 mg/kg for 4 days2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent.
AID243684Percentage inhibition against tryptase at 10 uM2005Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6
Combinatorial approaches towards the discovery of new tryptase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (383)

TimeframeStudies, This Drug (%)All Drugs %
pre-199074 (19.32)18.7374
1990's38 (9.92)18.2507
2000's100 (26.11)29.6817
2010's119 (31.07)24.3611
2020's52 (13.58)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.46

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index26.46 (24.57)
Research Supply Index6.10 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index50.07 (26.88)
Search Engine Supply Index3.19 (0.95)

This Compound (26.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials40 (9.93%)5.53%
Reviews17 (4.22%)6.00%
Case Studies24 (5.96%)4.05%
Observational1 (0.25%)0.25%
Other321 (79.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]