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Chemical Compound Review

Bromadal     N-aminocarbonyl-2-bromo-2- ethyl-butanamide

Synonyms: Bromadel, Parkosed, Pelidorm, CARBROMAL, Carbrital, ...
 
 
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Disease relevance of Somben

  • [reaction: see text] The unique solid-state hydration/dehydration properties of the diacid (+/-)-1e in comparison with other homologues of the same family are studied [1].
  • Structure of Chlorobium vibrioforme 5-aminolaevulinic acid dehydratase complexed with a diacid inhibitor [2].
  • The diacid conjugate was not toxic to A549 cells indicating further oxidation products of the mercapturic acids are not a factor in toxicity [3].
  • In addition, our data provide evidence that uncharged diacid is the species primarily interacting with the membrane as perturbation is favored by acidosis, a condition frequently associated with hyperbilirubinemia in premature and severely ill infants [4].
  • Enalaprilic acid (MK-422), the biologically active diacid of the converting enzyme inhibitor enalapril, was studied in myocardial ischemia (MI) [5].
 

High impact information on Somben

  • Accurate measurements of intracellular calcium activities in salivary gland epithelial cells of the insect Phormia regina were obtained with microelectrodes in which N,N'-di(11-ethoxycarbonyl)undecyl-N,N'-4,5-tetramethyl-3,6-dioxaoctane diacid diamide wsa incorporated in a liquid membrane system [6].
  • As in the case of the well-known aggregates of the related tetra(p-sulfonatophenyl)porphyrin (TSPP) diacid, the concentration of spectroscopically distinguishable aggregates increases with increasing ionic strength or decreasing pH [7].
  • The pharmacokinetic parameters for delapril, delapril diacid, and 5-hydroxy delapril diacid were, respectively: t 1/2 0.30, 1.21, and 1.40 hours; Cmax 489, 635, and 229 ng/ml; AUC 572, 1859, and 948 ng X hr/ml [8].
  • We compared PD 72953 to a structurally similar diacid, PD 69405, that also reduced VLDL and LDL, but had no effect on HDL elevation [9].
  • It is hydrolysed mainly in the gastrointestinal mucosa and liver to the active diacid, fosinoprilat, which has unique pharmacological properties [10].
 

Chemical compound and disease context of Somben

 

Biological context of Somben

  • Evidence in support of the conclusion that the mutase and dehydrogenase reactions are catalyzed at two similar but distinct active sites comes from the following results: (1) A substrate analogue (endo-oxabicyclic diacid) that inhibits competitively the mutase reaction has no effect on the dehydrogenase reaction [13].
  • To explore further structural concepts in drug design employed for the development of 1, several mono(benzyloxy) ketones (3-10) and alcohols (11-15) as well as a diacid (22) were prepared [14].
  • Lisinopril is an exception in that it is an enalaprilat-like diacid but with acceptable oral bioavailability, so that the prodrug route is not employed [15].
  • Similarly, the diacid diamide hydrolysis product of ADR-529 inhibited ferritin- and adriamycin-iron-dependent liposomal lipid peroxidation in a concentration-dependent manner [16].
  • 1. FPL 63547, in its active diacid form, was a potent inhibitor of rabbit lung angiotension converting enzyme (ACE) in vitro (IC50 0.51 nM) [17].
 

Anatomical context of Somben

  • In order to establish if the cytotoxic effect of the diacid is exerted equally in the absence of tyrosinase, lymphoma- and leukemia-derived cell lines were cultured for 72 hr with 10(-3) M, 10(-2) M and 5 X 10(-2) M C9 disodium salt [18].
  • Polarized efflux of mono- and diacid metabolites of ME3229, an ester-type prodrug of a glycoprotein IIb/IIIa receptor antagonist, in rat small intestine [19].
  • After i.v. or i.p. injections both Hoe 498 diacid and its prodrug Hoe 498 monoester (2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2- azabicyclo [3.3.0] octane-3-carboxylic acid) were detected in rat cerebrospinal fluid and the dipeptidyl carboxypeptidase activity in cerebrospinal fluid was inhibited [20].
  • The inhibitor, Hoe 498 diacid (2-[N-[(S)-1-carboxy-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyclo- [3.3.0] octane-3-carboxylic acid), was found to be highly effective in blocking YGGFMRF degradation by a dipeptidyl carboxypeptidase present in a preparation of mouse striatal microsomes [20].
  • We investigated the effects of ADR-529 and its hydrolysis products (the tetraacid and the diacid diamide) on NADPH- and ADP-Fe(3+)-dependent lipid peroxidation of rat liver microsomes and liposomes in the presence of cytochrome P-450 reductase [16].
 

Associations of Somben with other chemical compounds

  • The AUC of enalapril diacid increased 13-fold at CLCR values < 30 ml/min, but that of temocapril diacid increased only 2-fold [21].
  • Fosinopril is a prodrug which is converted to the active diacid in vivo, shows a relatively late peak time, a long terminal half-life, and is eliminated partially by the liver [22].
  • The pharmacodynamic profile of the new angiotensin-converting enzyme (ACE) inhibitor moexipril and its active diacid, moexiprilat, was studied in vitro and in vivo [23].
  • Crystals of dimethyl 2,6-cuneanedicarboxylate are disordered; the substitution pattern and structure have been confirmed by determination of the X-ray crystal structure of the corresponding diacid [24].
  • Subsequent addition of an aminoalkane, diaminoalkane, or alkane diacid dihydrazide gave rise to vitamin B(12) derivatives suitable for attachment to various proteins, peptides, or nanospheres to enable oral delivery utilizing the vitamin B(12) uptake system [25].
 

Gene context of Somben

  • These results demonstrate that mono- and diacid metabolites of ME3229 were pumped out into the gut lumen by an energy-dependent transport system located on the mucosal membrane of intestinal tissue and distinct from either P-gp, indomethacin-sensitive efflux pump or canalicular multispecific organic anion transporter/MRP2 [19].
  • Ramipril diacid given alone produced a small, nonsignificant increase in forearm flow, although the response was significantly related to basal plasma renin [26].
  • XPS indicates that diacid chlorides react primarily at one of their ends to create acyl chloride terminated surfaces in a single step [27].
  • Diacid-induced cytotoxicity was not attenuated by BNPP pretreatment [28].
  • This result, in conjunction with those showing a strong inhibitory effect of certain diacid derivatives, such as (+/-)-dimethylsuccinic acid, towards aldehyde reductase I, suggests the presence of two anion sites in or near the substrate binding site [29].
 

Analytical, diagnostic and therapeutic context of Somben

  • Atomic force microscopy (AFM) of porphyrin aggregates formed on silica from acidic aqueous solution is used to investigate the basis for the previously reported counterion dependence of the optical spectra of aggregates of H(2)TCPP(2+), the diacid form of tetra(p-carboxyphenyl)porphyrin (TCPP) [30].
  • The reactions catalyzed by carbapenam synthetase with different diastereomers of the natural substrate and with alternate alpha-amino diacid substrates were studied by HPLC, ESI mass spectrometry, and steady-state kinetic analysis [31].
  • The high-efficiency resolving power of the capillary electrophoresis system (20 microns x 27 cm column) separated the individual labeled drugs, and the antigen-antibody complexes were detected by laser-induced fluorescence (laser: 10 mW He-Ne at 632.8 nm) with Cy5 diacid as internal standard [32].
  • Biochemical analysis revealed that the diacid underwent beta-oxidation in all the cell cultures [18].
  • However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent beta-amino diacid, Ncma [33].

References

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  2. Structure of Chlorobium vibrioforme 5-aminolaevulinic acid dehydratase complexed with a diacid inhibitor. Coates, L., Beaven, G., Erskine, P.T., Beale, S.I., Wood, S.P., Shoolingin-Jordan, P.M., Cooper, J.B. Acta Crystallogr. D Biol. Crystallogr. (2005) [Pubmed]
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  4. Effects of bilirubin molecular species on membrane dynamic properties of human erythrocyte membranes: a spin label electron paramagnetic resonance spectroscopy study. Brito, M.A., Brondino, C.D., Moura, J.J., Brites, D. Arch. Biochem. Biophys. (2001) [Pubmed]
  5. Preservation of ischemic myocardium by a new converting enzyme inhibitor, enalaprilic acid, in acute myocardial infarction. Hock, C.E., Ribeiro, L.G., Lefer, A.M. Am. Heart J. (1985) [Pubmed]
  6. Calcium regulation during stimulus-secretion coupling: continuous measurement of intracellular calcium activities. O'Doherty, J., Youmans, S.J., Armstrong, W.M., Stark, R.J. Science (1980) [Pubmed]
  7. Counterion-dependent excitonic spectra of tetra(p-carboxyphenyl)porphyrin aggregates in acidic aqueous solution. Choi, M.Y., Pollard, J.A., Webb, M.A., McHale, J.L. J. Am. Chem. Soc. (2003) [Pubmed]
  8. Pharmacokinetics and depressor effect of delapril in patients with essential hypertension. Shionoiri, H., Yasuda, G., Ikeda, A., Ohta, T., Miyajima, E., Kaneko, Y. Clin. Pharmacol. Ther. (1987) [Pubmed]
  9. A novel compound that elevates high density lipoprotein and activates the peroxisome proliferator activated receptor. Bisgaier, C.L., Essenburg, A.D., Barnett, B.C., Auerbach, B.J., Haubenwallner, S., Leff, T., White, A.D., Creger, P., Pape, M.E., Rea, T.J., Newton, R.S. J. Lipid Res. (1998) [Pubmed]
  10. Fosinopril. Clinical pharmacokinetics and clinical potential. Shionoiri, H., Naruse, M., Minamisawa, K., Ueda, S., Himeno, H., Hiroto, S., Takasaki, I. Clinical pharmacokinetics. (1997) [Pubmed]
  11. Single-dose and steady-state pharmacokinetics of fosinopril and fosinoprilat in patients with hepatic impairment. Ford, N.F., Lasseter, K.C., Van Harken, D.R., Hammett, J.L., Raymond, R., Manning, J. Journal of clinical pharmacology. (1995) [Pubmed]
  12. Simultaneous measurement of renal blood flow of the outer and inner cortex by laser-Doppler flowmetry in anesthetized dogs: effect of enalapril diacid. Noguchi, K., Ojiri, Y., Chibana, T., Sakanashi, M. Archives internationales de pharmacodynamie et de thérapie. (1992) [Pubmed]
  13. Chorismate mutase-prephenate dehydrogenase from Escherichia coli. 2. Evidence for two different active sites. Turnbull, J., Morrison, J.F. Biochemistry (1990) [Pubmed]
  14. Synthesis and pharmacological evaluation of indanpropionic acids as uterine relaxants. Witiak, D.T., Hassan, A.M., Del Vecchio, F.R., Brumbaugh, R.J., Rahwan, R.G. J. Med. Chem. (1984) [Pubmed]
  15. Clinical pharmacokinetics of the newer ACE inhibitors. A review. Kelly, J.G., O'Malley, K. Clinical pharmacokinetics. (1990) [Pubmed]
  16. Effects of (+)-1,2-bis(3,5-dioxopiperazin-1-yl)propane (ADR-529) on iron-catalyzed lipid peroxidation. Ryan, T.P., Samokyszyn, V.M., Dellis, S., Aust, S.D. Chem. Res. Toxicol. (1990) [Pubmed]
  17. Pharmacological properties of FPL 63547, a novel inhibitor of angiotensin-converting enzyme. Carr, R.D., Higgs, L., Killingback, P.G., Nicol, A.K., O'Connor, S.E., Robson, A., Wells, E., Simpson, W.T. Br. J. Pharmacol. (1990) [Pubmed]
  18. Activity of azelaic acid on cultures of lymphoma- and leukemia-derived cell lines, normal resting and stimulated lymphocytes and 3T3 fibroblasts. Picardo, M., Passi, S., Sirianni, M.C., Fiorilli, M., Russo, G.D., Cortesi, E., Barile, G., Breathnach, A.S., Nazzaro-Porro, M. Biochem. Pharmacol. (1985) [Pubmed]
  19. Polarized efflux of mono- and diacid metabolites of ME3229, an ester-type prodrug of a glycoprotein IIb/IIIa receptor antagonist, in rat small intestine. Okudaira, N., Komiya, I., Sugiyama, Y. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  20. Inhibition of Met5-enkephalin-Arg6-Phe7 degradation by inhibitors of dipeptidyl carboxypeptidase. Mellstrom, B., Iadarola, M.J., Yang, H.Y., Costa, E. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
  21. Pharmacokinetics of temocapril and enalapril in patients with various degrees of renal insufficiency. Oguchi, H., Miyasaka, M., Koiwai, T., Tokunaga, S., Hora, K., Sato, K., Yoshie, T., Shioya, H., Furuta, S. Clinical pharmacokinetics. (1993) [Pubmed]
  22. Newer ACE inhibitors. A look at the future. Salvetti, A. Drugs (1990) [Pubmed]
  23. Moexipril, a new angiotensin-converting enzyme (ACE) inhibitor: pharmacological characterization and comparison with enalapril. Edling, O., Bao, G., Feelisch, M., Unger, T., Gohlke, P. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  24. Cubane, cuneane, and their carboxylates: a calorimetric, crystallographic, calculational, and conceptual coinvestigation. Roux, M.V., Dávalos, J.Z., Jiménez, P., Notario, R., Castaño, O., Chickos, J.S., Hanshaw, W., Zhao, H., Rath, N., Liebman, J.F., Farivar, B.S., Bashir-Hashemi, A. J. Org. Chem. (2005) [Pubmed]
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  26. Influence of ramipril diacid on the peripheral vascular effects of angiotensin I. Webb, D.J., Collier, J.G. Am. J. Cardiol. (1987) [Pubmed]
  27. First reaction of a bare silicon surface with acid chlorides and a one-step preparation of acid chloride terminated monolayers on scribed silicon. Lua, Y.Y., Fillmore, W.J., Yang, L., Lee, M.V., Savage, P.B., Asplund, M.C., Linford, M.R. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
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  29. The substrate binding site of aldehyde reductase from pig liver. Stereochemical investigations using NADP--2-oxodiacid adducts as probe. Branlant, G. Eur. J. Biochem. (1982) [Pubmed]
  30. Counterion dependent dye aggregates: nanorods and nanorings of tetra(p-carboxyphenyl)porphyrin. Doan, S.C., Shanmugham, S., Aston, D.E., McHale, J.L. J. Am. Chem. Soc. (2005) [Pubmed]
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  33. Total synthesis and absolute configuration of minalemine A, a guanidine peptide from the marine tunicate Didemnum rodriguesi. Expósito, A., Fernández-Suárez, M., Iglesias, T., Muñoz, L., Riguera, R. J. Org. Chem. (2001) [Pubmed]
 
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