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Chemical Compound Review

Beclamid     N-benzyl-3-chloro-propanamide

Synonyms: Beklamid, Neuracen, Posedran, Posedrin, Beclamida, ...
 
 
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Disease relevance of Beclamide

 

Psychiatry related information on Beclamide

 

High impact information on Beclamide

  • Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin [2].
  • Dextran derivatives with various substitution contents in carboxymethyl, benzylamide and sulfate groups were evaluated using a gel mobility shift assay [6].
  • Enantiomers of the alpha-methyl substituted benzylamide of 2-PC showed some ability to reduce seizure severity in amygdala kindled rats [7].
  • Functionalized dextrans (FD) are anionic water-soluble polymers bearing carboxylate, benzylamide and sulfate groups, which exhibit binding capacity to transforming growth factor-beta1 (TGF-beta1) [8].
  • Chemically modified dextrans modulate expression of collagen phenotype by cultured smooth muscle cells in relation to the degree of carboxymethyl, benzylamide, and sulfation substitutions [9].
 

Chemical compound and disease context of Beclamide

 

Biological context of Beclamide

  • Proceedings: Potential tolerance to beclamide and related drug interactions [11].
  • Carboxymethyl benzylamide dextrans inhibit breast cell growth [12].
  • Three CMBD derivatives showing an increasing proportion (5-14%) of benzylamide groups showed inhibition of bacterial adhesion increasing from 33 to 51% at 1 mg/ml [13].
  • In view of the simplicity of assay, beclamide may be a useful tool substance with which to examine factors influencing the xenobiotic metabolic pathways of benzene ring hydroxylation and glucuronide and sulphate conjugation in man [14].
  • The dissolution rate of beclamide from prepared microcapsules was determined by a rotating basket and the dissolution kinetics were investigated according to the zero-order, Hixson-Crowell and Higuchi equations [15].
 

Anatomical context of Beclamide

  • The concentrations of bioamines and their metabolites in the hypothalamus were unaffected by such acute beclamide treatment [16].
  • Several dextran derivatives obtained by substitution of methylcarboxylate (MC), benzylamide (B) and sulphate (Su) groups were used to determine the effects of each compound on fibroblast growth in vitro [17].
  • Water soluble derivatized dextran named E9 with a molecular weight of 45,000 g l-1 containing 58% methyl carboxylic acid unit, 19% benzylamide unit, and 26% sulfonate with a specific anticoagulant activity of 0.29 IU mg-1 was studied for its effects on human osteoblast growth and phenotype expression for short-term treatment [18].
 

Associations of Beclamide with other chemical compounds

 

Gene context of Beclamide

 

Analytical, diagnostic and therapeutic context of Beclamide

  • A simple method for the determination of beclamide in plasma by gas chromatography [24].
  • Following oral administration of 1 g beclamide to a panel of healthy volunteers, less than 0.4% of the dose was excreted unchanged in the 24-h urine and unconjugated 3- and 4-hydroxyphenyl metabolites were not detected [14].
  • A simple reverse phase HPLC assay is described for the determination of the anticonvulsant compound, beclamide and its 3- and 4-hydroxyphenyl metabolites in urine [14].
  • The o-nitrobenzyl tertiary benzylamide that is formed at the ligation junction can be transformed into a native amide group under mild photolysis conditions [25].
  • Studies on the masking of unpleasant taste of beclamide: microencapsulation and tabletting [15].

References

  1. Carboxymethyl benzylamide dextran blocks angiogenesis of MDA-MB435 breast carcinoma xenografted in fat pad and its lung metastases in nude mice. Bagheri-Yarmand, R., Kourbali, Y., Rath, A.M., Vassy, R., Martin, A., Jozefonvicz, J., Soria, C., Lu, H., Crépin, M. Cancer Res. (1999) [Pubmed]
  2. Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin. Choi, S.Y., Kim, S., Hwang, J.S., Lee, B.G., Kim, H., Kim, S.Y. Biochem. Pharmacol. (2004) [Pubmed]
  3. Carboxymethyl benzylamide dextran inhibits angiogenesis and growth of VEGF-overexpressing human epidermoid carcinoma xenograft in nude mice. Hamma-Kourbali, Y., Starzec, A., Vassy, R., Martin, A., Kraemer, M., Perret, G., Crépin, M. Br. J. Cancer (2003) [Pubmed]
  4. Regulation of the collagen phenotype expression of gamma-irradiated vascular smooth muscle cells by heparan mimetics (RGTA). Alexakis, C., Strup, C., Mestries, P., Mathé, D., Caruelle, J.P., Barritault, D., Kern, P. Journal of biomedical materials research. Part A. (2004) [Pubmed]
  5. Effects of beclamide on isolation-induced aggression and locomotor activity in mice. Darmani, N.A., Sewell, R.D., Nicholls, P.J. J. Pharm. Pharmacol. (1988) [Pubmed]
  6. Interaction of specifically chemically modified dextrans with transforming growth factor beta1: potentiation of its biological activity. Logeart-Avramoglou, D., Huynh, R., Chaubet, F., Sedel, L., Meunier, A. Biochem. Pharmacol. (2002) [Pubmed]
  7. Anticonvulsant activity of novel derivatives of 2- and 3-piperidinecarboxylic acid in mice and rats. Hinko, C.N., Crider, A.M., Kliem, M.A., Steinmiller, C.L., Seo, T.H., Ho, B., Venkatarangan, P., el-Assadi, A.A., Chang, H., Burns, C.M., Tietz, E.I., Andersen, P.H., Klitgaard, H. Neuropharmacology (1996) [Pubmed]
  8. Retention of transforming growth factor beta1 using functionalized dextran-based hydrogels. Maire, M., Logeart-Avramoglou, D., Degat, M.C., Chaubet, F. Biomaterials (2005) [Pubmed]
  9. Chemically modified dextrans modulate expression of collagen phenotype by cultured smooth muscle cells in relation to the degree of carboxymethyl, benzylamide, and sulfation substitutions. Mestries, P., Borchiellini, C., Barbaud, C., Duchesnay, A., Escartin, Q., Barritault, D., Caruelle, J.P., Kern, P. J. Biomed. Mater. Res. (1998) [Pubmed]
  10. Inhibition of epidermoid carcinoma A431 cell growth and angiogenesis in nude mice by early and late treatment with a novel dextran derivative. Di Benedetto, M., Starzec, A., Vassy, R., Perret, G.Y., Crépin, M., Kraemer, M. Br. J. Cancer (2003) [Pubmed]
  11. Proceedings: Potential tolerance to beclamide and related drug interactions. Luscombe, D.K., Nicholls, P.J. J. Pharm. Pharmacol. (1975) [Pubmed]
  12. Carboxymethyl benzylamide dextrans inhibit breast cell growth. Bagheri-Yarmand, R., Bittoun, P., Champion, J., Letourneur, D., Jozefonvicz, J., Fermandjian, S., Crépin, M. In Vitro Cell. Dev. Biol. Anim. (1994) [Pubmed]
  13. Inhibition by heparin and derivatized dextrans of Staphylococcus aureus adhesion to fibronectin-coated biomaterials. Vaudaux, P., Avramoglou, T., Letourneur, D., Lew, D.P., Jozefonvicz, J. Journal of biomaterials science. Polymer edition. (1992) [Pubmed]
  14. Metabolism of beclamide after a single oral dose in man: quantitative studies. Ahmadi, M., Nicholls, P.J., Smith, H.J., Spencer, P.S., Preet-Ryatt, M.S., Spragg, B.P. J. Pharm. Pharmacol. (1995) [Pubmed]
  15. Studies on the masking of unpleasant taste of beclamide: microencapsulation and tabletting. Ozer, A.Y., Hincal, A.A. Journal of microencapsulation. (1990) [Pubmed]
  16. Acute effects of beclamide on brain regional monoamine concentrations, their metabolites and radioligand binding studies. Darmani, N.A., Sewell, R.D., Nicholls, P.J. J. Pharm. Pharmacol. (1991) [Pubmed]
  17. Dextran derivatives modulate collagen matrix organization in dermal equivalent. Frank, L., Lebreton-Decoster, C., Godeau, G., Coulomb, B., Jozefonvicz, J. Journal of biomaterials science. Polymer edition. (2006) [Pubmed]
  18. Effect of a derivatized dextran on human osteoblast growth and phenotype expression. Berrada, S., Amedee, J., Avramoglou, T., Jozefonvicz, J., Harmand, M.F. Journal of biomaterials science. Polymer edition. (1994) [Pubmed]
  19. Inhibition by heparin and derivatized dextrans of Staphylococcus epidermidis adhesion to in vitro fibronectin-coated or explanted polymer surfaces. Francois, P., Letourneur, D., Lew, D.P., Jozefonwicz, J., Vaudaux, P. Journal of biomaterials science. Polymer edition. (1999) [Pubmed]
  20. Phthaloyl-glycylP-isoleucyl-tryptophan benzylamide is a potent inhibitor of human skin fibroblast collagenase with a Ki of 25 nM. Kortylewicz, Z.P., Galardy, R.E. J. Enzym. Inhib. (1989) [Pubmed]
  21. FGF protection and inhibition of human neutrophil elastase by carboxymethyl benzylamide sulfonate dextran derivatives. Meddahi, A., Lemdjabar, H., Caruelle, J.P., Barritault, D., Hornebeck, W. Int. J. Biol. Macromol. (1996) [Pubmed]
  22. Breast carcinoma cell uptake and biodistribution of technetium-99m-carboxymethyl benzylamide dextran. Bagheri-Yarmand, R., Moretti, J.L., Baba, K., Ozker, K., Jozefonvicz, J., Crepin, M. Anticancer Res. (2001) [Pubmed]
  23. Structurally different RGTAs modulate collagen-type expression by cultured aortic smooth muscle cells via different pathways involving fibroblast growth factor-2 or transforming growth factor-beta1. Alexakis, C., Mestries, P., Garcia, S., Petit, E., Barbier, V., Papy-Garcia, D., Sagot, M.A., Barritault, D., Caruelle, J.P., Kern, P. FASEB J. (2004) [Pubmed]
  24. A simple method for the determination of beclamide in plasma by gas chromatography. Jones, O.P., Leach, H., Luscombe, D.K., Nicholls, P.J. British journal of clinical pharmacology. (1975) [Pubmed]
  25. An o-nitrobenzyl scaffold for peptide ligation: synthesis and applications. Marinzi, C., Offer, J., Longhi, R., Dawson, P.E. Bioorg. Med. Chem. (2004) [Pubmed]
 
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