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Chemical Compound Review

Oleandocetin     [(2S,3R,4S,6R)-6- [[(3R,5S,6S,7R,8S,9R,12R...

Synonyms: Triocetin, Triolan, Viamicina, Wytrion, Aovine, ...
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Disease relevance of Triacetyloleandomycin

  • Trial of iloprost versus aspirin treatment for critical limb ischaemia of thromboangiitis obliterans. The TAO Study [1].
  • (2) Toxicity was prevented by pretreatment with a single dose of troleandomycin (a specific inhibitor of cytochromes P4503A) and enhanced by pretreatment with dexamethasone or clotrimazole (two inducers of cytochromes P4503A) [2].
  • Consistently, modulation of the tunnel shape, caused by the binding of the semi-synthetic macrolide troleandomycin to the large ribosomal subunit from Deinococcus radiodurans, was revealed crystallographically [3].
  • In vivo antitumor activity experiments revealed that TAO completely suppressed the ability of 90 microg/kg MMDX i.v., a dose close to the LD10, to delay growth of s.c. M5076 tumors in C57BL/6 mice and to prolong survival of DBA/2 mice with disseminated L1210 leukemia [4].
  • Moreover, TAO administration markedly inhibited the therapeutic efficacy of 90 microg/kg MMDX i.v. in mice bearing experimental M5076 liver metastases; a complete loss of MMDX activity was observed in liver metastases-bearing animals receiving 40 microg/kg MMDX i.v. plus TAO [4].

Psychiatry related information on Triacetyloleandomycin


High impact information on Triacetyloleandomycin


Chemical compound and disease context of Triacetyloleandomycin


Biological context of Triacetyloleandomycin


Anatomical context of Triacetyloleandomycin

  • Cytochrome P-450 isozyme LM3b from rabbit liver microsomes. Induction by triacetyloleandomycin purification and characterization [20].
  • To investigate the mechanism of induction of P-450p, we treated rats for 4 days with these agents and found that dexamethasone and TAO induced the synthesis of P-450p at least 70- and 35-fold over control values, respectively, as estimated from measurements of P-450p mRNA translatable in a cell-free system [21].
  • Prior incubation of microsomes with gestodene (100 microM) or troleandomycin (20 microM), known selective mechanism-based inhibitors of P-4503A enzymes (in the presence of NADPH), led to 75% and 40% reductions in catalytic activity, respectively [22].
  • We tested the latter possibility by studying the interaction of TAO and oleandomycin phosphate (OLEO), the active metabolite of TAO in vivo, with glucocorticoid receptors in dispersed, intact cultured human skin fibroblasts [19].
  • Mast cell stabilizers, anticholinergics, corticosteroids, and troleandomycin [23].

Associations of Triacetyloleandomycin with other chemical compounds


Gene context of Triacetyloleandomycin

  • Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450 [28].
  • In the present study we take advantage of recent advances in cDNA-directed human P450 expression to evaluate directly the P450 form selectivity of TAO, ANF, and DDC, using a panel of 10 individual cDNA-expressed human P450s [28].
  • Triacetyloleandomycin inhibited the reaction by approximately 90%, suggesting that CYP3A7 was primarily responsible for catalyzing the reaction [29].
  • The addition of the CYP3A subfamily selective inhibitor triacetyloleandomycin (1 microM) produced no statistically significant inhibition in reactions catalyzed by CYP1A1 or 1B1 SUPERSOMES [29].
  • Using furafyllin and troleandomycin to inhibit CYP1A2 and CYP3A4 in liver microsomes, it was found that the 2-hydroxylation had been inhibited about the same amount [30].

Analytical, diagnostic and therapeutic context of Triacetyloleandomycin

  • Oral administration of triacetyloleandomycin (TAO), 1 mmol/kg/day for 7 days to mature male New Zealand White rabbit results in a significant increase in the content of liver microsomal cytochrome P-450 [20].
  • High-performance liquid chromatography analysis revealed that RASMC were capable to metabolize CsA to its primary metabolites (AM1, AM9 and AM4N), and that their formation was inhibited by ketoconazole and troleandomycin [31].
  • RESULTS: Treatment with MP and TAO resulted in a clear reduction in respiratory symptoms, asthmatic attacks, corticosteroid and hospitalization requirements, improvement in pulmonary function tests, and a remarkable decrease in peak expiratory flow rate circadian variability when compared with the period before TAO treatment (with corticosteroids) [32].
  • The activities and levels of P450IIIA in hepatic microsomes from maternal rats and fetuses at 15-21 days of gestation were measured by triacetyloleandomycin (TAO) inhibited debenzylation of (benzyloxy)phenoxazone and by immunoassay with defined antiserum specific for P450IIIA [33].
  • The aim of treatment in patients with TAO is to make patients abstain from smoking to prevent ulceration and to shorten the period of healing of trophic lesions without major amputation, as ulceration and gangrene in T AO are limited to the most distal part of the limbs, and seems to have healing potential [34].


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  2. Hepatotoxicity of germander in mice. Loeper, J., Descatoire, V., Letteron, P., Moulis, C., Degott, C., Dansette, P., Fau, D., Pessayre, D. Gastroenterology (1994) [Pubmed]
  3. Structural insight into the role of the ribosomal tunnel in cellular regulation. Berisio, R., Schluenzen, F., Harms, J., Bashan, A., Auerbach, T., Baram, D., Yonath, A. Nat. Struct. Biol. (2003) [Pubmed]
  4. In vivo antitumor activity and host toxicity of methoxymorpholinyl doxorubicin: role of cytochrome P450 3A. Quintieri, L., Rosato, A., Napoli, E., Sola, F., Geroni, C., Floreani, M., Zanovello, P. Cancer Res. (2000) [Pubmed]
  5. Troleandomycin-triazolam interaction in healthy volunteers: pharmacokinetic and psychometric evaluation. Warot, D., Bergougnan, L., Lamiable, D., Berlin, I., Bensimon, G., Danjou, P., Puech, A.J. Eur. J. Clin. Pharmacol. (1987) [Pubmed]
  6. Cytochrome P450-generated reactive metabolites cause mitochondrial permeability transition, caspase activation, and apoptosis in rat hepatocytes. Haouzi, D., Lekéhal, M., Moreau, A., Moulis, C., Feldmann, G., Robin, M.A., Lettéron, P., Fau, D., Pessayre, D. Hepatology (2000) [Pubmed]
  7. Hepatotoxicity of the herbal medicine germander: metabolic activation of its furano diterpenoids by cytochrome P450 3A Depletes cytoskeleton-associated protein thiols and forms plasma membrane blebs in rat hepatocytes. Lekehal, M., Pessayre, D., Lereau, J.M., Moulis, C., Fouraste, I., Fau, D. Hepatology (1996) [Pubmed]
  8. Hepatic biotransformation of docetaxel (Taxotere) in vitro: involvement of the CYP3A subfamily in humans. Marre, F., Sanderink, G.J., de Sousa, G., Gaillard, C., Martinet, M., Rahmani, R. Cancer Res. (1996) [Pubmed]
  9. TAO (thousand-and-one amino acid) protein kinases mediate signaling from carbachol to p38 mitogen-activated protein kinase and ternary complex factors. Chen, Z., Raman, M., Chen, L., Lee, S.F., Gilman, A.G., Cobb, M.H. J. Biol. Chem. (2003) [Pubmed]
  10. Adrenocorticotrophin-induced hypertension: effects of mineralocorticoid and glucocorticoid receptor antagonism. Li, M., Wen, C., Fraser, T., Whitworth, J.A. J. Hypertens. (1999) [Pubmed]
  11. Biotransformation of 17 beta-hydroxy-11 beta-(4-dimethylaminophenyl)17 alpha-1-propynyl-estra-4,9-dien-3-one (RU486) in rat hepatoma variants. Chasserot-Golaz, S., Beck, G., Venetianer, A. Biochem. Pharmacol. (1993) [Pubmed]
  12. Digitoxin metabolism by liver microsomal cytochrome P-450 and UDP-glucuronosyltransferase and its role in the protection of rats from digitoxin toxicity by pregnenolone-16 alpha-carbonitrile. Arlotto, M.P., Sonderfan, A.J., McKinney, M.M., Parkinson, A. Arch. Biochem. Biophys. (1986) [Pubmed]
  13. Clinically significant drug interactions with agents specific for migraine attacks. Eadie, M.J. CNS drugs. (2001) [Pubmed]
  14. Bioactivation and toxicity in vitro of HCFC-123 and HCFC-141b: role of cytochrome P450. Zanovello, A., Ferrara, R., Tolando, R., Bortolato, S., White, I.N., Manno, M. Toxicol. Lett. (2001) [Pubmed]
  15. Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Chang, T.K., Weber, G.F., Crespi, C.L., Waxman, D.J. Cancer Res. (1993) [Pubmed]
  16. Clinical ergotism with lingual ischemia induced by clarithromycin-ergotamine interaction. Horowitz, R.S., Dart, R.C., Gomez, H.F. Arch. Intern. Med. (1996) [Pubmed]
  17. Cloning of a cDNA coding for P-450 LM3c from rabbit liver microsomes and regulation of its expression. Dalet, C., Blanchard, J.M., Guzelian, P., Barwick, J., Hartle, H., Maurel, P. Nucleic Acids Res. (1986) [Pubmed]
  18. Augmented arterial pressure responses to cyclosporine in spontaneously hypertensive rats. Role of cytochrome P-450 3A. Basu, A.K., Ghosh, S., Mohanty, P.K., Watlington, C.O. Hypertension (1994) [Pubmed]
  19. The effects of triacetyloleandomycin and oleandomycin phosphate on the glucocorticoid receptor in cultured skin fibroblasts. Engler, R.J., Chestnut, R.Y., Borst, G.C., Eil, C. J. Allergy Clin. Immunol. (1985) [Pubmed]
  20. Cytochrome P-450 isozyme LM3b from rabbit liver microsomes. Induction by triacetyloleandomycin purification and characterization. Bonfils, C., Dalet, C., Dalet-Beluche, I., Maurel, P. J. Biol. Chem. (1983) [Pubmed]
  21. Macrolide antibiotics inhibit the degradation of the glucocorticoid-responsive cytochrome P-450p in rat hepatocytes in vivo and in primary monolayer culture. Watkins, P.B., Wrighton, S.A., Schuetz, E.G., Maurel, P., Guzelian, P.S. J. Biol. Chem. (1986) [Pubmed]
  22. Human liver microsomal N-hydroxylation of dapsone by cytochrome P-4503A4. Fleming, C.M., Branch, R.A., Wilkinson, G.R., Guengerich, F.P. Mol. Pharmacol. (1992) [Pubmed]
  23. Mast cell stabilizers, anticholinergics, corticosteroids, and troleandomycin. Wynn, S.R. J. Allergy Clin. Immunol. (1989) [Pubmed]
  24. Taxol metabolism by human liver microsomes: identification of cytochrome P450 isozymes involved in its biotransformation. Cresteil, T., Monsarrat, B., Alvinerie, P., Tréluyer, J.M., Vieira, I., Wright, M. Cancer Res. (1994) [Pubmed]
  25. CYP3A4 is a human microsomal vitamin D 25-hydroxylase. Gupta, R.P., Hollis, B.W., Patel, S.B., Patrick, K.S., Bell, N.H. J. Bone Miner. Res. (2004) [Pubmed]
  26. Steroid-specific and anticonvulsant interaction aspects of troleandomycin-steroid therapy. Szefler, S.J., Ellis, E.F., Brenner, M., Rose, J.Q., Spector, S.L., Yurchak, A.M., Andrews, F., Jusko, W.J. J. Allergy Clin. Immunol. (1982) [Pubmed]
  27. A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans. Phimmasone, S., Kharasch, E.D. Clin. Pharmacol. Ther. (2001) [Pubmed]
  28. Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Chang, T.K., Gonzalez, F.J., Waxman, D.J. Arch. Biochem. Biophys. (1994) [Pubmed]
  29. Catalysis of drug oxidation during embryogenesis in human hepatic tissues using imipramine as a model substrate. Chen, H., Brzezinski, M.R., Fantel, A.G., Juchau, M.R. Drug Metab. Dispos. (1999) [Pubmed]
  30. Role of cytochrome P450 in estradiol metabolism in vitro. Cheng, Z.N., Shu, Y., Liu, Z.Q., Wang, L.S., Ou-Yang, D.S., Zhou, H.H. Acta Pharmacol. Sin. (2001) [Pubmed]
  31. Metabolism-dependent stimulation of reactive oxygen species and DNA synthesis by cyclosporin A in rat smooth muscle cells. Nguyen, N.S., Cottet-Maire, F., Buetler, T.M., Lo Russo, A., Krauskopf, A.S., Armstrong, J.M., Vickers, A.E., Macé, K., Rüegg, U.T. Free Radic. Biol. Med. (1999) [Pubmed]
  32. Troleandomycin in the treatment of difficult asthma. Siracusa, A., Brugnami, G., Fiordi, T., Areni, S., Severini, C., Marabini, A. J. Allergy Clin. Immunol. (1993) [Pubmed]
  33. Occurrence and inducibility of cytochrome P450IIIA in maternal and fetal rats during prenatal development. Hulla, J.E., Juchau, M.R. Biochemistry (1989) [Pubmed]
  34. Fate of the ischaemic limb in Buerger's disease. Ohta, T., Shionoya, S. The British journal of surgery. (1988) [Pubmed]
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