:Guanidinopropionic acid

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 431475088

| ImageFile = Guanidinopropionic acid.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 160

| ImageName = Skeletal formula of a guanidinopropionic acid minor tautomer

| IUPACName = 3-Carbamimidamidopropanoic acid{{cite web|title=3-guanidinopropanoic acid (CHEBI:15968)|url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15968|work=Chemical Entities of Biological Interest|publisher=European Bioinformatics Institute|accessdate=26 April 2012|location=UK|date=20 July 2010|at=Main}}

| OtherNames = 3-(Diaminomethylideneamino)propanoic acid{{citation needed|date=July 2012}}

|Section1={{Chembox Identifiers

| CASNo = 353-09-3

| CASNo_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UL1984YRKA

| PubChem = 67701

| ChemSpiderID = 61020

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| EINECS = 206-530-0

| KEGG = C03065

| KEGG_Ref = {{keggcite|changed|kegg}}

| MeSHName = guanidopropionic+acid

| ChEBI = 15968

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 20489

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| RTECS = AY3157500

| Beilstein = 1705262

| 3DMet = B00534

| SMILES = NC(=N)NCCC(O)=O

| StdInChI = 1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KMXXSJLYVJEBHI-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

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|Section2={{Chembox Properties

| C=4 | H=9 | N=3 | O=2

| Appearance = White crystals

| Odor = Odourless

| LogP = −1.472

| pKa = 4.219

| pKb = 9.778

}}

|Section3={{Chembox Hazards

| GHSPictograms = {{gHS exclamation mark}}

| GHSSignalWord = WARNING

| HPhrases = {{h-phrases|315|319|335}}

| PPhrases = {{p-phrases|261|305+351+338}}

}}

|Section4={{Chembox Related

| OtherFunction_label = alkanoic acids

| OtherFunction = {{unbulleted list|Sarcosine|Dimethylglycine|Glycocyamine|Creatine|N-Methyl-D-aspartic acid|beta-Methylamino-L-alanine|Arginine}}

| OtherCompounds = Dimethylacetamide

}}

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β-Guanidinopropionic acid, also referred to as guanidinopropionic acid, beta-guanidinopropionic acid or β-GPA, is a dietary supplement.

β-Guanidinopropionic acid, also known as Ompenaclid (RGX-202), is being investigated in colorectal cancer by Inspirna and Merck{{Cite web |title=Pipeline – Inspirna |url=https://inspirna.com/pipeline/ |access-date=2024-11-12 |website=inspirna.com}}

β-Guanidinopropionic acid is a white crystalline powder soluble in water (50 mg/ml-clear, colorless solution).{{ cite journal |author1=Bergeron, R. |author2=Ren, J. M. |author3=Cadman, K. S. |author4=Moore, I. K. |author5=Perret, P. |author6=Pypaert, M. |author7=Young, L. H. |author8=Semenkovich, C. F. |author9=Shulman, G. I. | year = 2001 | title = Chronic Activation of AMP Kinase Results in NRF-1 Activation and Mitochondrial Biogenesis | journal = American Journal of Physiology. Endocrinology and Metabolism | volume = 281 | issue = 6 | pages = E1340–E1346 | pmid = 11701451 | doi = 10.1152/ajpendo.2001.281.6.e1340 | s2cid = 21577702 }}

Studies on animals (rats, monkeys, hamsters) show that acidic guanidine derivatives such as β-GPA can ameliorate hyperglycemia in animal models of noninsulin-dependent diabetes.{{ cite journal |author1=Meglasson, M. D. |author2=Wilson, J. M. |author3=Yu, J. H. |author4=Robinson, D. D. |author5=Wyse, B. M. |author6=de Souza, C. J. |date=September 1993 | title = Antihyperglycemic Action of Guanidinoalkanoic Acids: 3-Guanidinopropionic Acid Ameliorates Hyperglycemia in Diabetic KKAy and C57BL6Job/ob Mice and Increases Glucose Disappearance in Rhesus Monkeys | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 266 | issue = 3 | pages = 1454–1462 |doi=10.1016/S0022-3565(25)39416-4 | pmid = 8371149 }}

Though the oral availability of β-GPA is well established, the basic uptake mechanism has not been studied yet.{{ cite journal |author1=Metzner, L. |author2=Dorn, M. |author3=Markwardt, F. |author4=Brandsch, M. |date=April 2009 | title = The Orally Active Antihyperglycemic Drug β-Guanidinopropionic Acid is Transported by the Human Proton-Coupled Amino Acid Transporter hPAT1 | journal = Molecular Pharmaceutics | volume = 6 | issue = 3 | pages = 1006–1011 | doi = 10.1021/mp9000684 | pmid = 19358571 }}