GLYCOCYAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H7N3O2
Molecular Weight	117.1066
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)NCC(O)=O

InChI

InChIKey=BPMFZUMJYQTVII-UHFFFAOYSA-N

InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)

HIDE SMILES / InChI

Molecular Formula	C3H7N3O2
Molecular Weight	117.1066
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
151.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25622538/	2.4 g single, oral dose: 2.4 g route of administration: Oral experiment type: SINGLE co-administered:		GLYCOCYAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
531.4 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25622538/	2.4 g single, oral dose: 2.4 g route of administration: Oral experiment type: SINGLE co-administered:		GLYCOCYAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.74 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25622538/	2.4 g single, oral dose: 2.4 g route of administration: Oral experiment type: SINGLE co-administered:		GLYCOCYAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
4.8 g 1 times / day multiple, oral Highest studied dose Dose: 4.8 g, 1 times / day Route: oral Route: multiple Dose: 4.8 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26079223/	healthy, mean age 22.5 years Health Status: healthy Age Group: mean age 22.5 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26079223/	Sources: https://pubmed.ncbi.nlm.nih.gov/26079223/
2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	Other AEs: Nausea, Stomach burning sensation of... Other AEs: Nausea (grade 1, 22.2%) Stomach burning sensation of (11.1%) Hyperhomocysteinaemia (55.6%) Creatinine serum increased (33.3%) AST increased (11.1%) ALT increased (11.1%) Creatine kinase increased (11.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27560540/ https://pubmed.ncbi.nlm.nih.gov/26840330/	healthy, mean age 24.3 years Health Status: healthy Age Group: mean age 24.3 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27560540/ https://pubmed.ncbi.nlm.nih.gov/26840330/	Other AEs: Blood homocysteine increased... Other AEs: Blood homocysteine increased (grade 1) Sources: https://pubmed.ncbi.nlm.nih.gov/27560540/ https://pubmed.ncbi.nlm.nih.gov/26840330/
48 mg/kg 1 times / day multiple, oral Studied dose Dose: 48 mg/kg, 1 times / day Route: oral Route: multiple Dose: 48 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/	healthy, mean age 24.8 years Health Status: healthy Age Group: mean age 24.8 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/	Other AEs: Stomach pain, Bloating... Other AEs: Stomach pain Bloating Constipation (grade 2) Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/

AEs

AE	Significance	Dose	Population
ALT increased	11.1%	2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
AST increased	11.1%	2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
Creatine kinase increased	11.1%	2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
Stomach burning sensation of	11.1%	2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
Creatinine serum increased	33.3%	2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
Hyperhomocysteinaemia	55.6%	2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
Nausea	grade 1, 22.2%	2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/	healthy, mean age 23.7 years Health Status: healthy Age Group: mean age 23.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23351309/
Blood homocysteine increased	grade 1	3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27560540/ https://pubmed.ncbi.nlm.nih.gov/26840330/	healthy, mean age 24.3 years Health Status: healthy Age Group: mean age 24.3 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27560540/ https://pubmed.ncbi.nlm.nih.gov/26840330/
Bloating		48 mg/kg 1 times / day multiple, oral Studied dose Dose: 48 mg/kg, 1 times / day Route: oral Route: multiple Dose: 48 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/	healthy, mean age 24.8 years Health Status: healthy Age Group: mean age 24.8 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/
Stomach pain		48 mg/kg 1 times / day multiple, oral Studied dose Dose: 48 mg/kg, 1 times / day Route: oral Route: multiple Dose: 48 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/	healthy, mean age 24.8 years Health Status: healthy Age Group: mean age 24.8 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/
Constipation	grade 2	48 mg/kg 1 times / day multiple, oral Studied dose Dose: 48 mg/kg, 1 times / day Route: oral Route: multiple Dose: 48 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/	healthy, mean age 24.8 years Health Status: healthy Age Group: mean age 24.8 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27497517/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	BGT1 4

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BGT1 4	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32781157/	yes [Km 403 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY550479	https://www.001chemical.com/chem/352-97-6
3B Scientific (Wuhan) Corp	3B3-035027	http://www.3bsc.com/index/pro_info.php?id=56960
AA Blocks	AA003QQW	http://www.aablocks.com/goods/Goods/detail?id=AA003QQW
Aaron Chemicals	AR003RIO	http://www.aaronchem.com/352-97-6
abcr GmbH	AB131511	http://www.abcr.com/shop/en/AB131511
abcr GmbH	AB180124	http://www.abcr.de/shop/en/AB180124
AbMole Bioscience	M10153	http://www.abmole.com/products/guanidineacetic-acid.html
Accela ChemBio Inc	SY015122	http://www.accelachem.com/cn/search.html?keyword=SY015122&attname=GoodsCode
Achemica	ACMC-209ifs	http://www.achemica.com/prodinfo/?id=126808
Achemtek	0104-020011	http://www.achemtek.com/352-97-6
AHH Chemical co.,ltd	MT-56471	http://www.ahhchemical.com/product/MT-56471.html
AK Scientific, Inc. (AKSCI)	165002	http://www.aksci.com/item_detail.php?cat=165002
AK Scientific, Inc. (AKSCI)	HTS001798	http://www.aksci.com/item_detail.php?cat=HTS001798
Alfa Aesar	L16281	https://www.alfa.com/en/catalog/L16281/
Alichem	471000805	http://www.alichem.com/en/products/352-97-6.html
Anward	ANW-28166	http://www.anward.com/pro_result/24294
Ark Pharm	AK144672	http://www.arkpharminc.com/products/352-97-6.html
Aurum Pharmatech LLC	M-3558	http://www.Aurumpharmatech.com/Product/ProductDetails/M_3558
Avantor Inc	101184-290	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101184-290
Avantor Inc	TCG0167-025G	https://us.vwr.com/store/product/10049587/glycocyamine-97-0-by-titrimetric-analysis
Avantor Inc	TCG0167-500G	https://us.vwr.com/store/product/10049587/glycocyamine-97-0-by-titrimetric-analysis
BioSynth	W-106678	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-106678.html
BLD Pharm	BD132232	http://www.bldpharm.com/products/352-97-6.html
BOC Sciences	634616-40-3	https://www.bocsci.com/guanidinoacetic-13c2-acid-cas-634616-40-3-item-241471.html
Chem Scene	CS-0040590	http://www.chemscene.com/352-97-6.html
ChemMol	49427027	http://www.chemmol.com/chemmol/49427027.html
Chemspace	CSSB00000742295	https://chem-space.com/CSSB00000742295
Clearsynth	CS-T-25730	https://www.clearsynth.com/en/CST25730.html
Clearsynth	CS-T-55462	https://www.clearsynth.com/en/CST55462.html
DC Chemicals	DC37348	http://www.dcchemicals.com//product_show-Glycocyamine.html
Debye Scientific	DB-069193	http://www.debyesci.com/cas_352-97-6.html
eNovation Chemicals	D388446	http://www.enovationchem.com/productDetails.asp?productID=D388446
eNovation Chemicals	D781345	https://www.enovationchem.com/ProductDetails.asp?ProductID=D781345
Finetech	FT-0626779	http://www.finetechnology-ind.com/prod/detail/pub/352-97-6.html
Finetech	FT-0669070	http://www.finetechnology-ind.com/prod/detail/pub/634616-40-3.html
Hairui	HR123411	http://www.hairuichem.com/en/product/352-97-6.html
Hefei Hirisun Pharmatech Co., Ltd	HR131462	http://hirisunpharm.com/352-97-6.html
iChemical	EBD37910	http://www.ichemical.com/products/352-97-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00198330	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00198330
mcule	MCULE-8327589872	https://mcule.com/MCULE-8327589872/
MedChem Express	HY-W021448	https://www.medchemexpress.com/2-Guanidinoacetic_acid.html
Molcore	MC550479	https://www.molcore.com/product/352-97-6
MuseChem	R012068	https://www.musechem.com/product/R012068.html
Oakwood	450285	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=168982&ExtHyperLink=1
Parchem	50408	https://www.parchem.com/chemical-supplier-distributor/Guanidine-acetic-acid--99%-050408.aspx
Renno Tech	RL03335	http://www.rennotech.com/product_show.asp?id=3584
Selleck Chemicals	S6340	http://www.selleckchem.com/products/guanidinoacetic-acid.html
Sigma-Aldrich	G11608_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/g11608?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S529035	http://www.smolecule.com/products/s529035
Smolecule	S793267	https://www.smolecule.com/products/s793267
TCI (Tokyo Chemical Industry)	G0167	http://www.tcichemicals.com/eshop/en/us/commodity/G0167/index.html
THE BioTek	bt-269331	https://www.thebiotek.com/product/inhibitors/bt-269331
Vitas-M Laboratory	BBL013464	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL013464&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL272669-100G	https://www.vladachem.com/product.php?products=352-97-6
Yuhao Chemical	JZ1558	http://www.chemyuhao.com/352-97-6.html

PubMed

Title	Date	PubMed
Age related changes in brain metabolites observed by 1H MRS in APP/PS1 mice.	2008-09	17434239
Successful treatment of a guanidinoacetate methyltransferase deficient patient: findings with relevance to treatment strategy and pathophysiology.	2007-07	17466557
Guanidinoacetate inhibits glutamate uptake in rat striatum of rats at different ages.	2007-06	17273928
Evidence that the inhibitory effects of guanidinoacetate on the activities of the respiratory chain, Na+,K+-ATPase and creatine kinase can be differentially prevented by taurine and vitamins E and C administration in rat striatum in vivo.	2007-05	17407807
A prevalent pathogenic GAMT mutation (c.59G>C) in Portugal.	2007-05	17336114
[Cerebral creatine transporter deficiency: an infradiagnosed neurometabolic disease].	2007-03-27	17385170
Treatment monitoring of brain creatine deficiency syndromes: a 1H- and 31P-MR spectroscopy study.	2007-03	17353334
Supervised group Lasso with applications to microarray data analysis.	2007-02-22	17316436
Reactome: a knowledge base of biologic pathways and processes.	2007	17367534
Overexpression of GAMT restores GAMT activity in primary GAMT-deficient fibroblasts.	2006-12	16899382
Reduced intestinal and renal amino acid transport in PDK1 hypomorphic mice.	2006-11	17077298
Influence of hematocrit and localisation of punch in dried blood spots on levels of amino acids and acylcarnitines measured by tandem mass spectrometry.	2006-11	16797519
High cerebral guanidinoacetate and variable creatine concentrations in argininosuccinate synthetase and lyase deficiency: implications for treatment?	2006-11	16580861
Methods for the diagnosis of creatine deficiency syndromes: a comparative study.	2006-09-30	16621013
Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds.	2006-09-11	16460903
[Diagnosis and treatment of brain creatine deficiency syndromes].	2006-08-31	16941429
Presymptomatic treatment of neonatal guanidinoacetate methyltransferase deficiency.	2006-08-22	16924036
GAMT deficiency: features, treatment, and outcome in an inborn error of creatine synthesis.	2006-08-08	16855203
S-adenosylhomocysteine hydrolase deficiency in a 26-year-old man.	2006-08	16736098
Biochemical validation of a rat model for polycystic kidney disease: comparison of guanidino compound profile with the human condition.	2006-06	16641922
Cerebral 1H MR spectroscopy showing elevation of brain guanidinoacetate in argininosuccinate lyase deficiency.	2006-05	16343968
Prenatal diagnosis of guanidinoacetate methyltransferase deficiency: increased guanidinoacetate concentrations in amniotic fluid.	2006-04	16595836
Increased guanidino species in murine and human succinate semialdehyde dehydrogenase (SSADH) deficiency.	2006-04	16504488
Intrastriatal administration of guanidinoacetate inhibits Na+, K+-ATPase and creatine kinase activities in rat striatum.	2006-03	16773469
Assay for the simultaneous determination of guanidinoacetic acid, creatinine and creatine in plasma and urine by capillary electrophoresis UV-detection.	2006-03	16605092
Quantitative short echo time 1H-MR spectroscopy of untreated pediatric brain tumors: preoperative diagnosis and characterization.	2006-03	16551993
Metabolic phenotyping of nude and normal (Alpk:ApfCD, C57BL10J) mice.	2006-02	16457604
Quantitative determination of guanidinoacetate and creatine in dried blood spot by flow injection analysis-electrospray tandem mass spectrometry.	2006-02	16197934
Theoretical study of the methyl transfer in guanidinoacetate methyltransferase.	2006-01-12	16471489
A mutation on exon 6 of guanidinoacetate methyltransferase (GAMT) gene supports a different function for isoform a and b of GAMT enzyme.	2006-01	16293431
Urinary excretion of guanidinoacetic acid in rats with diabetic nephropathy.	2006	16538977
Monitoring the effects of chronic alcohol consumption and abstinence on brain metabolism: a longitudinal proton magnetic resonance spectroscopy study.	2005-12-15	16084857
Folate, homocysteine, and arsenic metabolism in arsenic-exposed individuals in Bangladesh.	2005-12	16330347
1H MR spectroscopy of the brain in Cr transporter defect.	2005-11	16169765
Laboratory diagnosis of defects of creatine biosynthesis and transport.	2005-11	16169544
Phosphagen kinase of the giant tubeworm Riftia pachyptila. Cloning and expression of cytoplasmic and mitochondrial isoforms of taurocyamine kinase.	2005-10-30	16188310
The mimetics of antiadhesive peptides as the inhibitors of Mycobacterium kansasii phagocytosis.	2005-09	16112391
1H chemical shift imaging of the brain in guanidino methyltransferase deficiency, a creatine deficiency syndrome; guanidinoacetate accumulation in the gray matter.	2005-09	15856249
Origin and properties of cytoplasmic and mitochondrial isoforms of taurocyamine kinase.	2005-07	16008553
Urinary creatinine and arsenic metabolism.	2005-07	16002357
Lower force and impaired performance during high-intensity electrical stimulation in skeletal muscle of GAMT-deficient knockout mice.	2005-07	15743892
Creatine synthesis and transport during rat embryogenesis: spatiotemporal expression of AGAT, GAMT and CT1.	2005-05-26	15918910
Use of denaturing HPLC to provide efficient detection of mutations causing guanidinoacetate methyltransferase deficiency.	2005-05-17	16054853
Biochemical and behavioural phenotyping of a mouse model for GAMT deficiency.	2005-04-15	15792821
Creatine metabolism in combined methylmalonic aciduria and homocystinuria.	2005-04	15786446
Kinetic behavior of urea is different from that of other water-soluble compounds: the case of the guanidino compounds.	2005-04	15780113
A comprehensive update of the sequence and structure classification of kinases.	2005-03-16	15771780
[Creatine deficiency syndromes].	2005-03	15800449
Isolation, characterization, and cDNA-derived amino acid sequence of glycocyamine kinase from the tropical marine worm Namalycastis sp.	2005-03	15694586
L-arginine increases plasma homocysteine in apoE-/-/iNOS-/- double knockout mice.	2004-12	15704254

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:15 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:15 GMT 2025`
Record UNII	GO52O1A04E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMIDINOGLYCINE

Preferred Name

English

GLYCOCYAMINE

Systematic Name

English

NSC-227847

Code

English

2-((AMINO(IMINO)METHYL)AMINO)ACETIC ACID

Systematic Name

English

GUANIDINOACETIC ACID

Common Name

English

Glycocyamine [WHO-DD]

Common Name

English

GUANIDOACETIC ACID

Common Name

English

NSC-26360

Code

English

N-(AMINOIMINOMETHYL)GLYCINE

Systematic Name

English

GLYCOCYAMINE [MI]

Common Name

English

ACETIC ACID, ((AMINOIMINOMETHYL)AMINO)-

Common Name

English

GLYCINE, N-AMIDINO-

Systematic Name

English

GLYCINE, N-(AMINOIMINOMETHYL)-

Systematic Name

English

GUANIDINE, (CARBOXYMETHYL)-

Systematic Name

English

Guanidinoacetate

Common Name

English

GUANYL GLYCINE

Systematic Name

English

N-AMIDINOGLYCINE

Systematic Name

English

BETACYAMINE

Common Name

English

NSC-1901

Code

English

GUANIDINEACETIC ACID

Common Name

English

Classification Tree Code System Code

DSLD

1111 (Number of products:79)