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Chemical Compound Review

GLYCINAMID     2-aminoethanamide

Synonyms: Glycinamide, aminoacetamide, AmbotzHAA6570, CHEMBL86954, Glycine amide, ...
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Disease relevance of Glycine amide hydrochloride


High impact information on Glycine amide hydrochloride

  • The removal of glycinamide from the carboxy terminus of AVP drastically reduces its characteristic vasopressor and antidiuretic activities [6].
  • Asn102 of the gonadotropin-releasing hormone receptor is a critical determinant of potency for agonists containing C-terminal glycinamide [7].
  • These results, together with the sequence of the S. cerevisiae ADE8 gene encoding glycinamide ribotide transformylase, show that the entire Drosophila large polypeptide can be accounted for by the three enzymatic activities [8].
  • As a model for mechanistic comparison with peptidyl transfer within the ribosome, the reaction of aqueous glycinamide with N-formylphenylalanine trifluoroethyl ester (fPhe-TFE) represents an improvement over earlier model reactions involving Tris [9].
  • The transport of glycinamide across Caco-2 cell monolayers occurred via passive diffusion with an apparent permeability coefficient of about 2 x 10(-6) cm s(-1), which suggests that it is absorbed by the oral route in sufficient amounts to be considered for oral administration [10].

Biological context of Glycine amide hydrochloride


Anatomical context of Glycine amide hydrochloride


Associations of Glycine amide hydrochloride with other chemical compounds


Gene context of Glycine amide hydrochloride

  • Syntheses and biological properties are reported for two analogs of oxytocin in which the glycinamide and the leucylglycinamide moiety, respectively, have been deleted from the parent hormone [23].
  • In conclusion, the tripeptide GPG-amide acts as a prodrug that is activated by CD26 to release the orally active antiretroviral compound glycinamide [10].
  • 3. Pretreatment with L-deprenyl (2 mg kg-1), a specific inhibitor of monoamine oxidase type B (MAO-B), almost completely prevented the formation of glycinamide and increased milacemide accumulation in CSF [12].
  • Valproyl glycinamide, a new antiepileptic drug currently undergoing phase II clinical trials and its major metabolite valproyl glycine were weak mEH inhibitors [24].
  • Because the enzyme responsible for the cleavage of glycinamide from AVP was likely to be trypsin, experiments with aprotinin, a trypsin inhibitor, were conducted [25].

Analytical, diagnostic and therapeutic context of Glycine amide hydrochloride


  1. Transport of amino acid amide sarcosinamide and sarcosinamide chloroethylnitrosourea in human glioma SK-MG-1 cells. Skalski, V., Feindel, W., Panasci, L.C. Cancer Res. (1990) [Pubmed]
  2. N10-Formyltetrahydrofolate is the formyl donor for glycinamide ribotide transformylase in Escherichia coli. Dev, I.K., Harvey, R.J. J. Biol. Chem. (1978) [Pubmed]
  3. Arthrobacter D-xylose isomerase: chemical modification of carboxy groups and protein engineering of pH optimum. Siddiqui, K.S., Loviny-Anderton, T., Rangarajan, M., Hartley, B.S. Biochem. J. (1993) [Pubmed]
  4. Active and inactive L-prolyl-L-leucyl glycinamide synthetic analogs in rat models of levodopa-treated Parkinson's disease. Case, T.C., Snider, S.R., Hruby, V.J., Rockway, T. Life Sci. (1985) [Pubmed]
  5. A potential prebiotic route to adenine from hypoxanthine. Lagoja, I.M., Herdewijn, P. Chem. Biodivers. (2005) [Pubmed]
  6. Carboxy terminus of vasopressin required for activity but not binding. Manning, M., Olma, A., Klis, W., Kolodziejczyk, A., Nawrocka, E., Misicka, A., Seto, J., Sawyer, W.H. Nature (1984) [Pubmed]
  7. Asn102 of the gonadotropin-releasing hormone receptor is a critical determinant of potency for agonists containing C-terminal glycinamide. Davidson, J.S., McArdle, C.A., Davies, P., Elario, R., Flanagan, C.A., Millar, R.P. J. Biol. Chem. (1996) [Pubmed]
  8. The Saccharomyces cerevisiae ADE5,7 protein is homologous to overlapping Drosophila melanogaster Gart polypeptides. Henikoff, S. J. Mol. Biol. (1986) [Pubmed]
  9. The rate enhancement produced by the ribosome: an improved model. Schroeder, G.K., Wolfenden, R. Biochemistry (2007) [Pubmed]
  10. Orally active antiviral tripeptide glycyl-prolyl-glycinamide is activated by CD26 (dipeptidyl peptidase IV) before transport across the intestinal epithelium. Hubatsch, I., Lazorova, L., Vahlne, A., Artursson, P. Antimicrob. Agents Chemother. (2005) [Pubmed]
  11. Degradation of melanotropin inhibiting factor by brain. Hui, K.S., Cheng, K.P., Wong, K.H., Salschutz, M., Lajtha, A. J. Neurochem. (1980) [Pubmed]
  12. Antiepileptic drug pharmacokinetics and neuropharmacokinetics in individual rats by repetitive withdrawal of blood and cerebrospinal fluid: milacemide. Semba, J., Curzon, G., Patsalos, P.N. Br. J. Pharmacol. (1993) [Pubmed]
  13. Comparative pharmacokinetic and pharmacodynamic analysis of phthaloyl glycine derivatives with potential antiepileptic activity. abu Salach, O., Hadad, S., Haj-Yehia, A., Sussan, S., Bialer, M. Pharm. Res. (1994) [Pubmed]
  14. Application of Fourier transform infrared spectroscopy for monitoring hydrolysis and synthesis reactions catalyzed by a recombinant amidase. Pacheco, R., Karmali, A., Serralheiro, M.L., Haris, P.I. Anal. Biochem. (2005) [Pubmed]
  15. Structure-activity relationship study of R396, an NK2 tachykinin antagonist selective for the NK2B receptor subtype. Rovero, P., Astolfi, M., Manzini, S., Jukic, D., Rouissi, N., Maggi, C.A., Regoli, D. Neuropeptides (1992) [Pubmed]
  16. Interaction of L-prolyl-L-leucyl glycinamide with dopamine D2 receptor: evidence for modulation of agonist affinity states in bovine striatal membranes. Srivastava, L.K., Bajwa, S.B., Johnson, R.L., Mishra, R.K. J. Neurochem. (1988) [Pubmed]
  17. Simple and rapid micro-analytical procedures for the estimation of milacemide and its metabolite glycinamide in rat plasma and cerebrospinal fluid by high-performance liquid chromatography. Semba, J., Ratnaraj, N., Patsalos, P.N. J. Chromatogr. (1991) [Pubmed]
  18. Milacemide stimulates deficient glial Na+, K(+)-ATPase in freezing-induced epileptogenic cortex of cats. Laschet, J., Guillaume, D., Vergniolle-Burette, M., Grisar, T. Brain Res. (1990) [Pubmed]
  19. Pancreastatin--a novel regulatory peptide? Schmidt, W.E., Creutzfeldt, W. Acta oncologica (Stockholm, Sweden) (1991) [Pubmed]
  20. Membrane topology of guinea pig cytochrome P450 17 alpha revealed by a combination of chemical modifications and mass spectrometry. Izumi, S., Kaneko, H., Yamazaki, T., Hirata, T., Kominami, S. Biochemistry (2003) [Pubmed]
  21. Overview of phase I trials of multitargeted antifolate (MTA, LY231514). Rinaldi, D.A. Semin. Oncol. (1999) [Pubmed]
  22. Genetic evidence for a repressor of synthesis of cytosine deaminase and purine biosynthesis enzymes in Escherichia coli. Kilstrup, M., Meng, L.M., Neuhard, J., Nygaard, P. J. Bacteriol. (1989) [Pubmed]
  23. Synthetic metabolites of neurohypophyseal hormones. (Des-9-glycinamide)oxytocin and (des-9-glycinamide, des-8-leucine)oxytocin. Walter, R., Havran, R.T., Schwartz, I.L. J. Med. Chem. (1976) [Pubmed]
  24. Structure activity relationship of human microsomal epoxide hydrolase inhibition by amide and acid analogues of valproic acid. Spiegelstein, O., Kroetz, D.L., Levy, R.H., Yagen, B., Hurst, S.I., Levi, M., Haj-Yehia, A., Bialer, M. Pharm. Res. (2000) [Pubmed]
  25. Vasopressin is metabolized by a trypsinlike enzyme in guinea pig amniotic fluid. Uyehara, C.F., Sato, A.K., Claybaugh, J.R. Am. J. Physiol. (1989) [Pubmed]
  26. The structural requirements for the design of antiepileptic-glycine derivatives. Sussan, S., Dagan, A., Blotnik, S., Bialer, M. Epilepsy Res. (1999) [Pubmed]
  27. Recognition of imidazole and histamine derivatives by monoclonal antibodies. Morel, A., Darmon, M., Delaage, M. Mol. Immunol. (1990) [Pubmed]
  28. Pharmacokinetic analysis and antiepileptic activity of two new isomers of N-valproyl glycinamide. Hadad, S., Bialer, M. Biopharmaceutics & drug disposition. (1997) [Pubmed]
  29. Brain endo-oligopeptidase B: inactivation of LH-RH by hydrolysis of the Pro9-Gly-NH2(10) peptide bond. Camargo, A.C., Spadaro, A.C., Martins, A.R., Greene, L.J. Braz. J. Med. Biol. Res. (1982) [Pubmed]
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