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Guanidinopropionic acid

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Guanidinopropionic acid
Skeletal formula of a guanidinopropionic acid minor tautomer
Names
IUPAC name 3-Carbamimidamidopropanoic acid
Other names 3-(Diaminomethylideneamino)propanoic acid
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference 1705262
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.937 Edit this at Wikidata
EC Number
  • 206-530-0
KEGG
MeSH guanidopropionic+acid
PubChem CID
RTECS number
  • AY3157500
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)Key: KMXXSJLYVJEBHI-UHFFFAOYSA-N
SMILES
  • NC(=N)NCCC(O)=O
Properties
Chemical formula C4H9N3O2
Molar mass 131.135 g·mol
Appearance White crystals
Odor Odourless
log P −1.472
Acidity (pKa) 4.219
Basicity (pKb) 9.778
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P305+P351+P338
Related compounds
Related alkanoic acids
Related compounds Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

β-Guanidinopropionic acid is a white crystalline powder soluble in water (50 mg/ml-clear, colorless solution).

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.

Though the oral availability of β-GPA is well established, the basic uptake mechanism has not been studied yet.

References

  1. "3-guanidinopropanoic acid (CHEBI:15968)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 20 July 2010. Main. Retrieved 26 April 2012.
  2. "Pipeline – Inspirna". inspirna.com. Retrieved 2024-11-12.
  3. Bergeron, R.; Ren, J. M.; Cadman, K. S.; Moore, I. K.; Perret, P.; Pypaert, M.; Young, L. H.; Semenkovich, C. F.; Shulman, G. I. (2001). "Chronic Activation of AMP Kinase Results in NRF-1 Activation and Mitochondrial Biogenesis". American Journal of Physiology. Endocrinology and Metabolism. 281 (6): E1340–E1346. doi:10.1152/ajpendo.2001.281.6.e1340. PMID 11701451. S2CID 21577702.
  4. Meglasson, M. D.; Wilson, J. M.; Yu, J. H.; Robinson, D. D.; Wyse, B. M.; de Souza, C. J. (September 1993). "Antihyperglycemic Action of Guanidinoalkanoic Acids: 3-Guanidinopropionic Acid Ameliorates Hyperglycemia in Diabetic KKAy and C57BL6Job/ob Mice and Increases Glucose Disappearance in Rhesus Monkeys". The Journal of Pharmacology and Experimental Therapeutics. 266 (3): 1454–1462. PMID 8371149.
  5. Metzner, L.; Dorn, M.; Markwardt, F.; Brandsch, M. (April 2009). "The Orally Active Antihyperglycemic Drug β-Guanidinopropionic Acid is Transported by the Human Proton-Coupled Amino Acid Transporter hPAT1". Molecular Pharmaceutics. 6 (3): 1006–1011. doi:10.1021/mp9000684. PMID 19358571.
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