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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

ISONICOTINIC ACID     pyridine-4-carboxylic acid

Synonyms: PubChem2595, CHEMBL1203, SureCN1108, SureCN870989, NSC-1483, ...
 
 
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Disease relevance of isonicotinic acid

  • Quantitative structure-activity studies have been performed for a series of 2-substituted isonicotinic acid hydrazides by correlating electronic, steric, and lipophilic properties of the substituents with the biological activity date (MIC) from serial dilution tests with Mycobacterium tuberculosis (strain H 37 Rv) [1].
  • Mutagenic effects of isonicotinic acid hydracide in Fanconi's anemia [2].
  • The analysis of GC-MS showed that the katG I from M. bovis BCG directly converted INH (M(r), 137) to isonicotinamide (M(r), 122), not to isonicotinic acid (M(r), 123), in the presence or absence of H(2)O(2) [3].
  • 5. Neither the uninduced MAS nor the Aroclor 1254-induced MAS had an effect on any of the compounds tested and none of the MAS affected the developmental toxicity of INA [4].
 

High impact information on isonicotinic acid

 

Chemical compound and disease context of isonicotinic acid

 

Biological context of isonicotinic acid

 

Anatomical context of isonicotinic acid

  • Evidence for LT release was found in five out of six patients, following stimulation of the peripheral blood lymphocytes with INH or isonicotinic acid (INA) conjugated to human serum albumin [15].
  • The quaternary isonicotinic acid 2-butyne-1,4-diyl bisester (10b) displayed some functional selectivity for M2 receptors (-log EC50 = 5.78) [6- to 9-fold over M1/M4 (-log EC50/vas deferens = 5.03) and M3 receptors (-log EC50 = 4.83)] without showing nicotinic effects.(ABSTRACT TRUNCATED AT 250 WORDS)[16]
  • Late Xenopus laevis blastulae were exposed to INH, AH, and INA for 96 h in two separate static-renewal tests with and without the presence of three differently induced metabolic activation systems (MAS) [4].
 

Associations of isonicotinic acid with other chemical compounds

 

Gene context of isonicotinic acid

  • Renin inhibitors containing nicotinic or isonicotinic acid at the N-terminus. Part V [22].
  • We present an ab initio molecular dynamics study of the complex between acyl carrier protein reductase InhA from M. tuberculosis and isonicotinic acid hydrazide-NADH [23].
 

Analytical, diagnostic and therapeutic context of isonicotinic acid

References

  1. Mode of action and quantitative structure-activity correlations of tuberculostatic drugs of the isonicotinic acid hydrazide type. Seydel, J.K., Schaper, K.J., Wempe, E., Cordes, H.P. J. Med. Chem. (1976) [Pubmed]
  2. Mutagenic effects of isonicotinic acid hydracide in Fanconi's anemia. Schroeder, T.M., Stahl-Maugé, C. Hum. Genet. (1979) [Pubmed]
  3. Catalase-peroxidase of Mycobacterium bovis BCG converts isoniazid to isonicotinamide, but not to isonicotinic acid: Differentiation parameter between enzymes of Mycobacterium bovis BCG and Mycobacterium tuberculosis. Kang, S.K., Lee, J.H., Lee, Y.C., Kim, C.H. Biochim. Biophys. Acta (2006) [Pubmed]
  4. Analysis of the mechanism of isoniazid-induced developmental toxicity with frog embryo teratogenesis assay: Xenopus (FETAX). Fort, D.J., Bantle, J.A. Teratog., Carcinog. Mutagen. (1990) [Pubmed]
  5. Isoniazid hepatoxicity: the relationship between covalent binding and metabolism in vivo. Timbrell, J.A., Mitchell, J.R., Snodgrass, W.R., Nelson, S.D. J. Pharmacol. Exp. Ther. (1980) [Pubmed]
  6. Bioactive 1,4-dihydroisonicotinic acid derivatives prevent oxidative damage of liver cells. Borovic, S., Tirzitis, G., Tirzite, D., Cipak, A., Khoschsorur, G.A., Waeg, G., Tatzber, F., Scukanec-Spoljar, M., Zarkovic, N. Eur. J. Pharmacol. (2006) [Pubmed]
  7. Spontaneously Resolved Homochiral 3D Lanthanide-Silver Heterometallic Coordination Framework with Extended Helical Ln-O-Ag Subunits. Gu, X., Xue, D. Inorganic chemistry (2006) [Pubmed]
  8. Anticlastogenicity of two derivatives of 1,4-dihydroisonicotinic acid in mouse micronucleus test. Goncharova, R., Zabrejko, S., Dalivelya, O., Kuzhir, T. Mutat. Res. (2001) [Pubmed]
  9. Metabolism of isoniazid by activated leukocytes. Possible role in drug-induced lupus. Hofstra, A.H., Li-Muller, S.M., Uetrecht, J.P. Drug Metab. Dispos. (1992) [Pubmed]
  10. Acetylator phenotyping of tuberculosis patients using matrix isoniazid or sulphadimidine and its prognostic significance for treatment with several intermittent isoniazid-containing regimens. Ellard, G.A., Gammon, P.T. British journal of clinical pharmacology. (1977) [Pubmed]
  11. Some effects of 1,4-dihydroisonicotinic acid derivatives on repair pathways involved in chemical mutagenesis. Kuzhir, T.D., Goncharova, R.I. Biochem. Soc. Trans. (1997) [Pubmed]
  12. Usefulness of graphical invariants in quantitative structure-activity correlations of tuberculostatic drugs of the isonicotinic acid hydrazide type. Bagchi, M.C., Maiti, B.C., Mills, D., Basak, S.C. Journal of molecular modeling (Online) (2004) [Pubmed]
  13. Carbonic anhydrase inhibitors. Water-soluble, topically effective intraocular pressure lowering agents derived from isonicotinic acid and aromatic/heterocyclic sulfonamides: is the tail more important than the ring? Menabuoni, L., Scozzafava, A., Mincione, F., Briganti, F., Mincione, G., Supuran, C.T. J. Enzym. Inhib. (1999) [Pubmed]
  14. Induction of differentiation in human promyelocytic leukemia HL-60 cell line by niacin-related compounds. Iwata, K., Ogata, S., Okumura, K., Taguchi, H. Biosci. Biotechnol. Biochem. (2003) [Pubmed]
  15. Lymphocyte-mediated cytotoxicity in isoniazid-associated hepatitis. Warrington, R.J., Olivier, S.L. Clin. Exp. Immunol. (1979) [Pubmed]
  16. Aliphatic and heterocyclic analogues of arecaidine propargyl ester. Structure-activity relationships of mono- and bivalent ligands at muscarinic M1 (M4), M2 and M3 receptor subtypes. Moser, U., Gubitz, C., Galvan, M., Immel-Sehr, A., Lambrecht, G., Mutshcler, E. Arzneimittel-Forschung. (1995) [Pubmed]
  17. An investigation of the surface-enhanced Raman scattering (SERS) effect from a new substrate of silver-modified silver electrode. Wen, R., Fang, Y. Journal of colloid and interface science. (2005) [Pubmed]
  18. Niacin. II: Identification of isonicotinic acid in niacin by liquid chromatography with diode array detection. Kirchhoefer, R.D. Journal of AOAC International. (1994) [Pubmed]
  19. Identification of a cytochrome P450 cDNA (CYP98A5) from Phaseolus vulgaris, inducible by 3,5-dichlorosalicylic acid and 2,6-dichloro isonicotinic acid. Basson, A.E., Dubery, I.A. J. Plant Physiol. (2007) [Pubmed]
  20. Synthesis of pyridine nucleotide analogs consisting of nicotinoylamino acids by means of transglycosidation reactions catalyzed by mammalian pyridine nucleotide transglycosidases. Imai, T., Hatori, M. J. Nutr. Sci. Vitaminol. (2002) [Pubmed]
  21. Carrier-mediated uptake of nicotinic acid by rat intestinal brush-border membrane vesicles and relation to monocarboxylic acid transport. Simanjuntak, M.T., Tamai, I., Terasaki, T., Tsuji, A. J. Pharmacobio-dyn. (1990) [Pubmed]
  22. Renin inhibitors containing nicotinic or isonicotinic acid at the N-terminus. Part V. Paruszewski, R., Jaworski, P., Tautt, J., Dudkiewicz, J. Bollettino chimico farmaceutico. (1995) [Pubmed]
  23. NADH interactions with WT- and S94A-acyl carrier protein reductase from Mycobacterium tuberculosis: an ab initio study. Pantano, S., Alber, F., Lamba, D., Carloni, P. Proteins (2002) [Pubmed]
  24. Isoniazid induces expression of the antigen 85 complex in Mycobacterium tuberculosis. Garbe, T.R., Hibler, N.S., Deretic, V. Antimicrob. Agents Chemother. (1996) [Pubmed]
  25. Use of a long-lifetime Re(I) complex in fluorescence polarization immunoassays of high-molecular-weight analytes. Guo, X.Q., Castellano, F.N., Li, L., Lakowicz, J.R. Anal. Chem. (1998) [Pubmed]
  26. Detection of IgE antibodies specific to isonicotinic acid hydrazide and its metabolite by enzyme-linked immunosorbent assay and the mechanism of sensitization by inhalation or ingestion of this compound. Shimoda, T. Arerugi (1990) [Pubmed]
 
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