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Chemical Compound Review:

GNF-PF-1199 2-phenylethanamide

Synonyms: PubChem13418, CPD-238, SureCN25676, AGN-PC-0D9X2J, CHEMBL347645, ...

Stiene-Martin, A. et al., Devine, D.P. et al., McDonald, C.E. et al., Utz, J. et al., Karmali, A. et al., et al.

Done, Brannigan, Moody, Hubbard, Tabacova, Kimmel, Wall, Hansen,

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Disease relevance of Phenylacetic acid amide

The effects of the selective kappa opioid receptor agonist U-50488H (trans-3,4-dichloro-N-methyl-N[2-(pyrrolidinyl)-cyclohexyl]- benzeneacetamide) were examined in acute head and spinal injury models [1].
Mutants able to utilize phenylacetamide as sole nitrogen source were isolated from the acetanilide (N-phenylacetamide) - utilizing Pseudomonas aeruginosa mutant strain A13 and from its parent strain L 10 [2].
BACKGROUND: Atenolol, 4-2'-hydroxy-3'-isopropyl-aminopropoxy) phenylacetamide, is a beta-adrenoreceptor blocker used for treatment of hypertension in pregnancy [3].

High impact information on Phenylacetic acid amide

The kappa opioid agonist (5alpha,7alpha,8beta)-(-)-N-methyl-N-(7-(1-pyrrolidinyl)-1-oxaspiro(4,5)dec-8-yl) benzeneacetamide (U69,593) induced Tyr and Ser phosphorylation of EGFR and activation of ERK [4].
Studies have shown that the enzyme is specific for hydrolysis of phenylacetamide derivatives, but is more tolerant of features in the rest of the substrate [5].
Selective mu (PLO 17; H-Tyr-Pro-Phe (N-Me) -D-Pro-NH2, delta ([D-Pen2, D-Pen5] enkephalin), or kappa (U50,488H; trans-(+/-)-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl) cyclohexyl] benzeneacetamide methanesulfonate) opioid receptor agonists increased [Ca2+]i in subpopulations of astrocytes indicating the presence of functional receptors [6].
The influence of substitutions on the phenylacetamide aromatic ring on binding at both the sigma1 and sigma2 receptor has been examined through Hansch-type quantitative structure-activity relationship (QSAR) studies [7].
A 3-h pretreatment with a kappa-selective agonist, (+/-)-trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl] benzeneacetamide (U50,488), caused receptor down-regulation, whereas no receptor down-regulation was found after levorphanol pretreatment [8].

Biological context of Phenylacetic acid amide

Selective and enantiospecific acylation of kappa opioid receptors by (1S,2S)-trans-2-isothiocyanato-N-methyl-N-[2-(1-pyrrolidinyl) cyclohexy l] benzeneacetamide. Demonstration of kappa receptor heterogeneity [9].
BW942C was less efficacious in producing diuresis than the full kappa agonists bremazocine and U50,488H (trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]- benzeneacetamide methanesulfonate, hydrate) [10].
A kappa (kappa) opioid binding site has been characterized on the macrophage cell line, P388d1, using the kappa selective affinity ligand, [3H] (1S,2S)-(-)-trans-2-isothiocyanato-N-methyl-N-[2-(1- pyrrolidinyl) cyclohexyl] benzeneacetamide (-)BD166) [11].

Anatomical context of Phenylacetic acid amide

The only drug that displayed a significant action on hair-cell ionic currents was trans-(+/-)-3,4-dichloro-N-methyl-N-(2-[1-pyrrolidinyl]-cyclohexyl) benzeneacetamide methanesulfonate (U-50488) that reduced the Ca(2+) current in a dose-dependent fashion [12].
In guinea pig ventricular myocytes the kappa-opioid agonist trans(+/-)-3,3-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]- benzeneacetamide methanesulfonate salt (U50488H) inhibited L-type calcium currents (ICa) as measured by the patch clamp technique in a dose-dependent fashion [13].

Associations of Phenylacetic acid amide with other chemical compounds

In the mouse abdominal constriction test, pretreatment with the nitric oxide synthase (NOS) inhibitor L-NG-nitroarginine (L-NOARG) caused dose-related antagonism of the antinociceptive effect of N2O but not of either morphine or trans(+/-)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl] benzeneacetamide methane sulfonate [14].
VTA microinjections of (trans-(dl)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclo-hexyl]- benzeneacetamide) methane sulfonate hydrate (U-50,488H); a kappa agonist) failed to alter ventral striatal DA concentrations at any dose tested, but subsequent systemic injections significantly decreased DA and DA-metabolite concentrations [15].
U-50,488, (trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]- benzeneacetamide hydrochloride), is a selective kappa-opioid receptor agonist [16].
A mutation in a gene designated gmdA has been found to lead to loss of ability of Aspergillus nidulans to use benzamide, phenylacetamide and several other amides as sole nitrogen sources for growth [17].

Gene context of Phenylacetic acid amide

The kappa-opioid receptor agonist, U50,488H (trans-(+-)-3,4-dichloro-N-methyl-[2-(1-pyrrolidinyl)-cyclohexyl]- benzeneacetamide), has recently been reported to induce dystonia after s.c. administration of 5-10 mg/kg in guinea pigs [18].
The wild-type and mutant amidase genes (W138G, T103I-W138G, and T103I) were cloned into an expression vector and these enzymes were purified by affinity chromatography on epoxy-activated Sepharose 6B-acetamide/phenylacetamide followed by gel filtration chromatography [19].

References

Beneficial effects of the kappa opioid receptor agonist U-50488H in experimental acute brain and spinal cord injury. Hall, E.D., Wolf, D.L., Althaus, J.S., Von Voigtlander, P.F. Brain Res. (1987) [Pubmed]
Adaptation to phenylacetamide as a growth substrate by an acetanilide-utilizing mutant of Pseudomonas aeruginosa. Gregoriou, M., Brown, P.R. Arch. Microbiol. (1980) [Pubmed]
Atenolol developmental toxicity: animal-to-human comparisons. Tabacova, S., Kimmel, C.A., Wall, K., Hansen, D. Birth defects research. Part A, Clinical and molecular teratology. (2003) [Pubmed]
Mu opioid transactivation and down-regulation of the epidermal growth factor receptor in astrocytes: implications for mitogen-activated protein kinase signaling. Belcheva, M.M., Tan, Y., Heaton, V.M., Clark, A.L., Coscia, C.J. Mol. Pharmacol. (2003) [Pubmed]
Ligand-induced conformational change in penicillin acylase. Done, S.H., Brannigan, J.A., Moody, P.C., Hubbard, R.E. J. Mol. Biol. (1998) [Pubmed]
Regional, developmental, and cell cycle-dependent differences in mu, delta, and kappa-opioid receptor expression among cultured mouse astrocytes. Stiene-Martin, A., Zhou, R., Hauser, K.F. Glia (1998) [Pubmed]
Synthesis and quantitative structure-activity relationships of N-(1-benzylpiperidin-4-yl)phenylacetamides and related analogues as potent and selective sigma1 receptor ligands. Huang, Y., Hammond, P.S., Whirrett, B.R., Kuhner, R.J., Wu, L., Childers, S.R., Mach, R.H. J. Med. Chem. (1998) [Pubmed]
Differential agonist regulation of the human kappa-opioid receptor. Blake, A.D., Bot, G., Li, S., Freeman, J.C., Reisine, T. J. Neurochem. (1997) [Pubmed]
Selective and enantiospecific acylation of kappa opioid receptors by (1S,2S)-trans-2-isothiocyanato-N-methyl-N-[2-(1-pyrrolidinyl) cyclohexy l] benzeneacetamide. Demonstration of kappa receptor heterogeneity. de Costa, B.R., Rothman, R.B., Bykov, V., Jacobson, A.E., Rice, K.C. J. Med. Chem. (1989) [Pubmed]
Kappa opioid partial agonist activity of the enkephalin-like pentapeptide BW942C based on urination and in vitro studies in humans and animals. Vaupel, D.B., Cone, E.J., Johnson, R.E., Su, T.P. J. Pharmacol. Exp. Ther. (1990) [Pubmed]
Enantioselective kappa opioid binding sites on the macrophage cell line, P388d1. Carr, D.J., DeCosta, B.R., Jacobson, A.E., Rice, K.C., Blalock, J.E. Life Sci. (1991) [Pubmed]
Opioid receptors mediate a postsynaptic facilitation and a presynaptic inhibition at the afferent synapse of axolotl vestibular hair cells. Vega, R., Soto, E. Neuroscience (2003) [Pubmed]
Inhibition of L-type calcium currents in guinea pig ventricular myocytes by the kappa-opioid agonist U50488H does not involve binding to opiate receptors. Utz, J., Eckert, R., Trautwein, W. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
Inhibitors of nitric oxide synthesis antagonize nitrous oxide antinociception in mice and rats. McDonald, C.E., Gagnon, M.J., Ellenberger, E.A., Hodges, B.L., Ream, J.K., Tousman, S.A., Quock, R.M. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
Differential involvement of ventral tegmental mu, delta and kappa opioid receptors in modulation of basal mesolimbic dopamine release: in vivo microdialysis studies. Devine, D.P., Leone, P., Pocock, D., Wise, R.A. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
U-50,488 blocks the development of morphine tolerance and dependence at a very low dose in guinea pigs. Tao, P.L., Hwang, C.L., Chen, C.Y. Eur. J. Pharmacol. (1994) [Pubmed]
Amide utilization in Aspergillus nidulans: evidence for a third amidase enzyme. Hynes, M.J. J. Gen. Microbiol. (1975) [Pubmed]
The kappa-opioid receptor agonist, U50,488H, exerts antidystonic activity in a mutant hamster model of generalized dystonia. Richter, A., Löscher, W. Eur. J. Pharmacol. (1993) [Pubmed]
Substitutions of Thr-103-Ile and Trp-138-Gly in amidase from Pseudomonas aeruginosa are responsible for altered kinetic properties and enzyme instability. Karmali, A., Pacheco, R., Tata, R., Brown, P. Mol. Biotechnol. (2001) [Pubmed]

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