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Chemical Compound Review

AC1LA6X6     N-[[(2R,3S,4R,5R,6S)-5-amino- 6-[(1R,2R,3S...

Synonyms: Pyrene carbonyl substituted neamine
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Disease relevance of PCN

  • In this article, we review our experience with rapid intravenous desensitization for patients who gave a history of PCN allergy and who had hypersensitivity demonstrated by skin tests [1].
  • Patients allergic to penicillin (PCN) often require treatment with beta-lactam antibiotics for life-threatening bacterial infections [1].
  • A mutation in the psrA gene (Pseudomonas sigma regulator), the gene product of which is a member of the TetR/AcrR family of transcriptional regulators, resulted in increased production of autoinducer molecules and PCN [2].
  • Since the substantia nigra pars reticulata (SNpr) seems to have an inhibitory action on the ventro-anterior (VA) and ventro-lateral (VL) thalamic nuclei and thalamic neurones send an excitatory influence to the cortex, we undertook an investigation to study nigral influence on cortical epilepsy induced by PCN [3].
  • The results showed that a microinjection of PCN in the AM produced a reliable model of interictal spikes, paroxysms and generalized convulsive seizures [4].

Psychiatry related information on PCN


High impact information on PCN

  • The sequence of NF25 is 77% similar to that reported for a rat cytochrome "P-450PCN" cDNA (PCN = pregnenolone-16 alpha-carbonitrile) [6].
  • AcCho applied directly to PCN somata depolarizes them, indicating that the PCN soma membrane contains AcCho receptors and induces the FMP in the isolated central nervous system preparation [7].
  • Incubation of 4-OH-tam with liver microsomes from PCN-treated rat yielded three detectable metabolites [8].
  • Expression of wild type PXR and various mutants as green fluorescent fusion proteins in mouse livers showed that PXR was retained in the cytoplasm from where PCN treatment translocated PXR into the nucleus [9].
  • We conclude that the CCRP mediates the retention of PXR in the cytosol and modulates the activation of PXR in response to PCN treatment [9].

Chemical compound and disease context of PCN


Biological context of PCN

  • To determine the role of the amide group in biocontrol, the PCN biosynthetic genes of strain PCL1391 were identified and characterized [14].
  • CONCLUSION: Overall, one-week combination regimens of PCA and PCN present similar H. pylori eradication efficacy [15].
  • Our previous work unraveled a cascade of genes regulating the PCN biosynthesis operon, phzABCDEFGH [10].
  • The expression of the PCN biosynthetic gene cluster in PCL1391 is population density-dependent and is regulated by the quorum-sensing genes phzI and phzR via synthesis of the autoinducer N-hexanoyl-L-homoserine lactone (C6-HSL) [2].
  • Two PCL1391 mutants lacking production of PCN were defective in the genes phzI and phzR, respectively, the nucleotide sequences of which were determined completely [16].

Anatomical context of PCN

  • In experiments on seven cats we tested the hypothesis that the epileptogenic effect of penicillin (PCN) on the spinal cord is mediated by a reduction of presynaptic inhibition [17].
  • The authors present a case of papillary and cystic neoplasm of the pancreas (PCN) in which fine-needle aspiration was performed intraoperatively [18].
  • The features most helpful in reaching a diagnosis of PCN were a monotonous population of tumor cells, round to oval bland-appearing nuclei, scanty to moderate ill-defined cytoplasm, and the presence of numerous capillaries [18].
  • Cellular locations, axonal projections, and synaptic effects of inhibitory vestibulocollic (VC) neurons activated by the ampullary nerve of the posterior semicircular canal (PCN) were studied in anesthetized cats [19].
  • PB and PCN treatments increased thyroid weight 80%, and PTU increased thyroid weight 500% [20].

Associations of PCN with other chemical compounds


Gene context of PCN

  • Chromatin immunoprecipitation (ChIP) from liver nuclei showed that aging had no effect on the activity of an IR0 enhancer in the Sult2A1 chromatin to recruit VDR, RXR-alpha (retinoid X receptor) and PXR in mice injected with D(3) or PCN [24].
  • We have used a specific anti-PXR antibody in the Western blotting of mouse liver nuclear extracts to show that PXR is accumulated in the nucleus after treatment with 5-pregnen-3beta-ol-20-one-16alpha-carbonitrile (PCN), followed by an increase in Cyp3a11 mRNA [9].
  • FA does not alter expression of the PCN regulators gacS, rpoS and psrA [26].
  • Taken together, these results indicated that the inhibition of histone deacetylation was required to SXR-mediated increase in CYP3A4 proximal promoter region when rifampicin, or PCN was treated [27].
  • Human fetal and adult liver metabolism of ethylmorphine. Relation to immunodetected cytochrome P-450 PCN and interactions with important fetal corticosteroids [28].

Analytical, diagnostic and therapeutic context of PCN

  • Of seven different MAbs used MAb PCN 2-13-1/C2 was the only one that immunodetected a cytochrome P-450 band with Western blot analyses of human fetal liver microsomes [25].
  • A combination of a phenotypical characterization of a pip mutant, in trans complementation assays of various mutant strains, and electrophoretic mobility shift assays identified Pip as the fifth DNA-binding protein so far involved in regulation of PCN biosynthesis [10].
  • Repeated microinjections of PCN did not produce lasting alterations in sleep onset and organization [4].
  • In addition, we have shown that BICUC and PCN produced membrane depolarization of mouse spinal cord neurons in primary dissociated cell culture by blocking a potassium conductance, a non-synaptic direct effect [29].
  • A retrospective study of a focused history and PCN skin testing was done in a consecutive sample of a suburban allergy population of 319 patients who had a positive history of PCN allergy [30].


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  2. The Pseudomonas chlororaphis PCL1391 sigma regulator psrA represses the production of the antifungal metabolite phenazine-1-carboxamide. Chin-A-Woeng, T.F., van den Broek, D., Lugtenberg, B.J., Bloemberg, G.V. Mol. Plant Microbe Interact. (2005) [Pubmed]
  3. Inhibitory control by substantia nigra of generalized epilepsy in the cat. Sabatino, M., Gravante, G., Ferraro, G., Savatteri, V., La Grutta, V. Epilepsy Res. (1988) [Pubmed]
  4. Repeated penicillin-induced amygdala epileptic focus in freely moving cats. EEG, polysomnographic (23-h recording), and brain mapping study. Fernández-Guardiola, A., Martínez, A., Fernández-Mas, R. Epilepsy Res. (1995) [Pubmed]
  5. Central inhibitory effect of Moringa oleifera root extract: possible role of neurotransmitters. Ray, K., Hazrai, R., Guha, D. Indian J. Exp. Biol. (2003) [Pubmed]
  6. Isolation and sequence determination of a cDNA clone related to human cytochrome P-450 nifedipine oxidase. Beaune, P.H., Umbenhauer, D.R., Bork, R.W., Lloyd, R.S., Guengerich, F.P. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  7. Cholinergic suppression: a postsynaptic mechanism of long-term associative learning. Morielli, A.D., Matera, E.M., Kovac, M.P., Shrum, R.G., McCormack, K.J., Davis, W.J. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  8. Evidence that the catechol 3,4-Dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins. Dehal, S.S., Kupfer, D. Cancer Res. (1996) [Pubmed]
  9. Cytoplasmic localization of pregnane X receptor and ligand-dependent nuclear translocation in mouse liver. Squires, E.J., Sueyoshi, T., Negishi, M. J. Biol. Chem. (2004) [Pubmed]
  10. Pip, a Novel Activator of Phenazine Biosynthesis in Pseudomonas chlororaphis PCL1391. Girard, G., Barends, S., Rigali, S., van Rij, E.T., Lugtenberg, B.J., Bloemberg, G.V. J. Bacteriol. (2006) [Pubmed]
  11. Phenazines and other redox-active antibiotics promote microbial mineral reduction. Hernandez, M.E., Kappler, A., Newman, D.K. Appl. Environ. Microbiol. (2004) [Pubmed]
  12. A survey of antibiotic prescribing and knowledge of penicillin allergy. Puchner, T.C., Zacharisen, M.C. Ann. Allergy Asthma Immunol. (2002) [Pubmed]
  13. Induction of ABCC3 (MRP3) by pregnane X receptor activators. Teng, S., Jekerle, V., Piquette-Miller, M. Drug Metab. Dispos. (2003) [Pubmed]
  14. Introduction of the phzH gene of Pseudomonas chlororaphis PCL1391 extends the range of biocontrol ability of phenazine-1-carboxylic acid-producing Pseudomonas spp. strains. Chin-A-Woeng, T.F., Thomas-Oates, J.E., Lugtenberg, B.J., Bloemberg, G.V. Mol. Plant Microbe Interact. (2001) [Pubmed]
  15. Proton pump inhibitor, clarithromycin and either amoxycillin or nitroimidazole: a meta-analysis of eradication of Helicobacter pylori. Gisbert, J.P., González, L., Calvet, X., García, N., López, T., Roqué, M., Gabriel, R., Pajares, J.M. Aliment. Pharmacol. Ther. (2000) [Pubmed]
  16. Phenazine-1-carboxamide production in the biocontrol strain Pseudomonas chlororaphis PCL1391 is regulated by multiple factors secreted into the growth medium. Chin-A-Woeng, T.F., van den Broek, D., de Voer, G., van der Drift, K.M., Tuinman, S., Thomas-Oates, J.E., Lugtenberg, B.J., Bloemberg, G.V. Mol. Plant Microbe Interact. (2001) [Pubmed]
  17. Presynaptic and long-lasting postsynaptic inhibition during penicillin-induced spinal seizures. Davenport, J., Schwindt, P.C., Crill, W.E. Neurology (1978) [Pubmed]
  18. Aspiration cytology of papillary cystic neoplasm of the pancreas. Katz, L.B., Ehya, H. Am. J. Clin. Pathol. (1990) [Pubmed]
  19. Localization and synaptic effects of inhibitory vestibulocollic neurons activated by the posterior semicircular canal nerve in the cat. Isu, N., Sakuma, A., Hiranuma, K., Ichikawa, T., Uchino, Y. Neurosci. Lett. (1990) [Pubmed]
  20. Effects of phenobarbital, pregnenolone-16alpha-carbonitrile, and propylthiouracil on thyroid follicular cell proliferation. Hood, A., Liu, J., Klaassen, C.D. Toxicol. Sci. (1999) [Pubmed]
  21. The effects of roxatidine acetate on 24-hour intragastric acidity. Investigations in healthy volunteers and comparison with ranitidine and placebo. Merki, H.S., Witzel, L., Kaufmann, D., Kempf, M., Neumann, J., Scheurle, E., Röhmel, J., Walt, R.P. Drugs (1988) [Pubmed]
  22. Interactions in the tomato rhizosphere of two Pseudomonas biocontrol strains with the phytopathogenic fungus Fusarium oxysporum f. sp. radicis-lycopersici. Bolwerk, A., Lagopodi, A.L., Wijfjes, A.H., Lamers, G.E., Chin-A-Woeng, T.F., Lugtenberg, B.J., Bloemberg, G.V. Mol. Plant Microbe Interact. (2003) [Pubmed]
  23. Influence of environmental conditions on the production of phenazine-1-carboxamide by Pseudomonas chlororaphis PCL1391. van Rij, E.T., Wesselink, M., Chin-A-Woeng, T.F., Bloemberg, G.V., Lugtenberg, B.J. Mol. Plant Microbe Interact. (2004) [Pubmed]
  24. Xenobiotic- and vitamin D-responsive induction of the steroid/bile acid-sulfotransferase Sult2A1 in young and old mice: The role of a gene enhancer in the liver chromatin. Seo, Y.K., Chung, Y.T., Kim, S., Echchgadda, I., Song, C.S., Chatterjee, B. Gene (2007) [Pubmed]
  25. Monoclonal antibody directed detection of cytochrome P-450 (PCN) in human fetal liver. Ladona, M.G., Park, S.S., Gelboin, H.V., Hammar, L., Rane, A. Biochem. Pharmacol. (1988) [Pubmed]
  26. Influence of fusaric acid on phenazine-1-carboxamide synthesis and gene expression of Pseudomonas chlororaphis strain PCL1391. van Rij, E.T., Girard, G., Lugtenberg, B.J., Bloemberg, G.V. Microbiology (Reading, Engl.) (2005) [Pubmed]
  27. Trichostatin A, a histone deacetylase inhibitor stimulate CYP3A4 proximal promoter activity in Hepa-I cells. Ahn, M.R., Kim, D.K., Sheen, Y.Y. Arch. Pharm. Res. (2004) [Pubmed]
  28. Human fetal and adult liver metabolism of ethylmorphine. Relation to immunodetected cytochrome P-450 PCN and interactions with important fetal corticosteroids. Ladona, M.G., Spalding, D.J., Ekman, L., Linström, B., Rane, A. Biochem. Pharmacol. (1989) [Pubmed]
  29. Membrane depolarization and prolongation of calcium-dependent action potentials of mouse neurons in cell culture by two convulsants: bicuculline and penicillin. Heyer, E.J., Nowak, L.M., Macdonald, R.L. Brain Res. (1982) [Pubmed]
  30. Prevalence of skin test reactivity in patients with convincing, vague, and unacceptable histories of penicillin allergy. Stember, R.H. Allergy and asthma proceedings : the official journal of regional and state allergy societies. (2005) [Pubmed]
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