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Chemical Compound Review

Propanamide     propanamide

Synonyms: Propylamide, propioamide, PROPIONAMIDE, ACMC-1BJ8Y, AG-C-18497, ...
 
 
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Psychiatry related information on propanamide

  • The preliminary screening results indicated that omega-phthalimido-N-phenylacetamide and propionamide nuclei have pronounced anticonvulsant activity against maximal electroshock seizure [1].
  • Thirteen amenorrheic patients, two with primary amenorrhea, and eleven with secondary amenorrhea, including five with anorexia nervosa, were treated with an analog of LH-RH, D-Ala-6-desGly-10-LH-RH propylamide (D-Ala-6-LH-RH PA) [2].
 

High impact information on propanamide

  • Calculations show that when Cu(H2O)(4)2+ combines with the model compound 1 (3-(1H-imidazol-5-yl)-N-[2-(1H-imidazol-5-yl)ethyl] propanamide) in the aqueous phase, the most stable binding site involves the Npi atoms of His13 and His14 as well as the carbonyl of the intervening backbone amide group [3].
  • Pharmacokinetics and metabolism of a selective androgen receptor modulator in rats: implication of molecular properties and intensive metabolic profile to investigate ideal pharmacokinetic characteristics of a propanamide in preclinical study [4].
  • N-butyl, N-hexyl, and N,N-dioctyl propanamide derivatives of E2 (IC50 values of 6.4, 2.8, and >20 microM, respectively) were less potent inhibitors than N-octyl analog 15 [5].
  • In this study we have shown that although bombesin cannot stimulate ACTH secretion alone, it potentiates release by ovine CRF, an effect blocked by the GRP receptor antagonist D-Tyr6bombesin (6-13) propylamide [6].
  • The vitamin D3 hydroxylase-associated protein is a propionamide-metabolizing amidase enzyme [7].
 

Biological context of propanamide

 

Anatomical context of propanamide

  • To corroborate these results, we treated brain membranes with the site directed alkylating agent FIT (N-phenyl-N-[1-(2-p-isothiocyanato)phenyl-ethyl)-4-piperidinyl] propanamide), which results in membranes highly enriched with the lower affinity [3H]DADL binding site [8].
  • Propionamide is the best substrate with a Vmax of 16.7 nmol NH4+/min/mg protein and an apparent Km of 7.9 mM in soluble chicken kidney mitochondria [7].
  • Another known inhibitor of transport, colchicine (COL) also caused a significant decrease in the percent of neurites with a GAP-43 accumulation; propionamide (PA), a non-neurotoxic analogue of ACR, had no effect on protein accumulation [9].
  • The PBR ligand [3H]PK 11195 had high affinity for the expressed receptor in COS-1 cells, but the affinities of a pair of isoquinoline propanamide enantiomers differed remarkably in expressed and endogenous human PBR [10].
  • Of the acyl groups, 4-carboxybutyryl appears most advantageous, propylamide is the most suitable of alkylamides for pancreatic elastase, and isobutylamide for leukocyte elastase [11].
 

Associations of propanamide with other chemical compounds

  • The highest acyl transferase activity was detected with hexanoamide, isobutyramide and propionamide [12].
  • Devrinol 50-DF "napropamide" [N,N-diethyl-2-(1-naphthyloxy) propionamide] was applied as a preemergent herbicide, incorporated into the soil surface, and the plots were planted with 60-day-old sweet bell pepper seedlings [13].
  • RESULTS: Pinacidil and its analog P1075 (N-cyano-N'-(1,1-dimethylpropyl)-N"-3-pyridylguanidine), ZD6169 (N-(4-benzoylphenyl)-3,3,3,-trifluoro-2-hydroxy-2-methyl propionamide), and the enantiomers of cromakalim evoked concentration-dependent decreases in DiBAC4(3) fluorescence responses [14].
  • Three of the new compounds, N-[2-(2-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl]acetamide (9), and the respective propionamide 10 and butyramide 11, are as potent as melatonin in the Xenopus laevis melanophore model [15].
  • The pharmacokinetics of 3-(decyldimethylsilyl)-N-[2-(4-methylphenyl)-1- phenylethyl] propanamide (DMPP), an inhibitor of acyl-CoA: cholesterol acyltransferase, have been examined in 18 healthy male volunteers who received an oral dose of either 14C-DMPP or 3H-DMPP immediately following a high-fat meal, or 3H-DMPP in the fasting state [16].
 

Gene context of propanamide

  • Three vitamin B12 (cyanocobalamin) conjugates bearing one nido-carborane molecule or two nido-carborane molecules linked to the propionamide side chains via a four carbon linker have been synthesized [17].
  • In this study, twenty omega-[2-oxo-3H-benzoxazol-3-yl]-N-phenylacetamide and propionamide derivatives having substituents of different lipophilic and electronic nature on the N-phenyl ring were synthesized to evaluate the inhibitory effects on in vitro leukocyte MPO chlorinating activity [18].
 

Analytical, diagnostic and therapeutic context of propanamide

  • Quantitative determination of N-(trans-2-dimethylaminocyclopentyl)-N-(3',4'-dichlorophenyl) propanamide and its N-demethyl metabolite in dog serum by gas chromatography [19].

References

  1. The synthesis and anticonvulsant activity of some omega-phthalimido-N-phenylacetamide and propionamide derivatives. Soyer, Z., Kilic, F.S., Erol, K., Pabuccuoglu, V. Arch. Pharm. (Weinheim) (2004) [Pubmed]
  2. Attempts to induce ovulation in amenorrheic patients using D-Ala-6-LH-RH propylamide. Cortés-Prieto, J., Arencibia-Rocha, J., Aranda, A., García-García, M.D., Coy, D.H., Schally, A.V. Int. J. Fertil. (1979) [Pubmed]
  3. Ab initio model studies of copper binding to peptides containing a His-His sequence: relevance to the beta-amyloid peptide of Alzheimer's disease. Raffa, D.F., Gómez-Balderas, R., Brunelle, P., Rickard, G.A., Rauk, A. J. Biol. Inorg. Chem. (2005) [Pubmed]
  4. Pharmacokinetics and metabolism of a selective androgen receptor modulator in rats: implication of molecular properties and intensive metabolic profile to investigate ideal pharmacokinetic characteristics of a propanamide in preclinical study. Wu, D., Wu, Z., Yang, J., Nair, V.A., Miller, D.D., Dalton, J.T. Drug Metab. Dispos. (2006) [Pubmed]
  5. 17Alpha-alkan (or alkyn) amide derivatives of estradiol as inhibitors of steroid-sulfatase activity. Boivin, R.P., Labrie, F., Poirier, D. Steroids (1999) [Pubmed]
  6. Bombesin regulation of adrenocorticotropin release from ovine anterior pituitary cells. Au, C.L., Canny, B.J., Farnworth, P.G., Giraud, A.S. Peptides (1997) [Pubmed]
  7. The vitamin D3 hydroxylase-associated protein is a propionamide-metabolizing amidase enzyme. Ettinger, R.A., DeLuca, H.F. Arch. Biochem. Biophys. (1995) [Pubmed]
  8. Morphine tolerance increases mu-noncompetitive delta binding sites. Rothman, R.B., Danks, J.A., Jacobson, A.E., Burke, T.R., Rice, K.C., Tortella, F.C., Holaday, J.W. Eur. J. Pharmacol. (1986) [Pubmed]
  9. Decreased GAP-43 accumulation in neurite tips of cultured hippocampal neurons by acrylamide. Clarke, C.H., Sickles, D.W. Neurotoxicology (1996) [Pubmed]
  10. The human "peripheral-type" benzodiazepine receptor: regional mapping of the gene and characterization of the receptor expressed from cDNA. Chang, Y.J., McCabe, R.T., Rennert, H., Budarf, M.L., Sayegh, R., Emanuel, B.S., Skolnick, P., Strauss, J.F. DNA Cell Biol. (1992) [Pubmed]
  11. Anionic inhibitors of pancreatic and leukocyte elastase. Alkylamides of 3-carboxypropionyl- and 4-carboxybutyrylalanine peptides. Kasafírek, E., Fric, P., Slabý, J. Biol. Chem. Hoppe-Seyler (1985) [Pubmed]
  12. Purification and properties of an enantioselective and thermoactive amidase from the thermophilic actinomycete Pseudonocardia thermophila. Egorova, K., Trauthwein, H., Verseck, S., Antranikian, G. Appl. Microbiol. Biotechnol. (2004) [Pubmed]
  13. Napropamide residues in runoff and infiltration water from pepper production. Antonious, G.F., Patterson, M.A. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. (2005) [Pubmed]
  14. Fluorescence-based functional assay for sarcolemmal ATP-sensitive potassium channel activation in cultured neonatal rat ventricular myocytes. Whiteaker, K.L., Davis-Taber, R., Scott, V.E., Gopalakrishnan, M. Journal of pharmacological and toxicological methods. (2001) [Pubmed]
  15. Synthesis of new tricyclic melatoninergic ligands. Tsotinis, A., Panoussopoulou, M., Sivananthan, S., Sugden, D. Farmaco (2001) [Pubmed]
  16. Influence of high-fat meal on the absorption of a silicon-containing amide, an inhibitor of acyl-CoA: cholesterol acyltransferase, in man. Tse, F.L., Jaffe, J.M. Biopharmaceutics & drug disposition. (1988) [Pubmed]
  17. Synthesis and characterization of nido-carborane-cobalamin conjugates. Hogenkamp, H.P., Collins, D.A., Live, D., Benson, L.M., Naylor, S. Nucl. Med. Biol. (2000) [Pubmed]
  18. Synthesis of some 2(3H)-benzoxazolone derivatives and their in-vitro effects on human leukocyte myeloperoxidase activity. Soyer, Z., Bas, M., Pabuccuoglu, A., Pabuccuoglu, V. Arch. Pharm. (Weinheim) (2005) [Pubmed]
  19. Quantitative determination of N-(trans-2-dimethylaminocyclopentyl)-N-(3',4'-dichlorophenyl) propanamide and its N-demethyl metabolite in dog serum by gas chromatography. Lakings, D.B., Stryd, R.P., Gilbertson, T.J. Journal of pharmaceutical sciences. (1984) [Pubmed]
 
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