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Chemical Compound Review

cinchonine     (5-ethenyl-1- azabicyclo[2.2.2]oct-7-yl)...

Synonyms: CINCHONIDINE, Cinchovatine, Cinchonan-9-ol, GNF-PF-5411, CHEMBL15134, ...
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Disease relevance of NSC5364


High impact information on NSC5364

  • Serum from rats treated with i.v. cinchonine produced greater uptake of doxorubicin in cancer cells (DHD/K12/PROb rat colon cells and K562/ADM human leukemic cells) than did serum from quinine-treated rats (ex vivo assay) [1].
  • In the Pt-catalyzed hydrogenation of 1,1,1-trifluoro-2,4-diketones, addition of trace amounts of cinchonidine, O-methyl-cinchonidine, or (R,R)-pantoyl-naphthylethylamine induces up to 93% ee and enhances the chemoselectivity up to 100% in the hydrogenation of the activated carbonyl group to an OH function [4].
  • Optically active (S)-alpha-amino acids are prepared in 54-95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base [5].
  • Phase I study of cinchonine, a multidrug resistance reversing agent, combined with the CHVP regimen in relapsed and refractory lymphoproliferative syndromes [6].
  • The MTD of cinchonine administered by continuous i.v. infusion was 30 mg/kg/d. Prolonged cardiac repolarization was the main dose-limiting toxicity [6].

Chemical compound and disease context of NSC5364


Biological context of NSC5364

  • This study was conducted to examine the effect of cinchonine on human platelet aggregation [8].
  • Catalytic enantioselective alkylation promoted by a quaternary ammonium salt from cinchonine as a phase transfer catalyst is described [9].
  • The depression induced by cinchonine was noticeable only at 100 mg/l. Chemotaxis was decreased by about 25% (formyl-methionyl-leucyl-phenylalanine) or 39% (serum) for quinine (100 mg/l) only if a constant concentration of the drug was maintained during the assay while cinchonine had no effect on this PMN function [10].
  • Cinchonine was most effective in inhibiting aggregation induced by platelet activating factor and epinephrine with IC50 values of 125 and 180 microM respectively, however, higher concentrations of cinchonine were required to inhibit aggregation mediated by ADP or collagen (IC50; 300 microM) [8].
  • The pharmacokinetics of cinchonine and quinine administered po in rat are shown to be very different [11].

Anatomical context of NSC5364


Associations of NSC5364 with other chemical compounds


Gene context of NSC5364


Analytical, diagnostic and therapeutic context of NSC5364


  1. Cinchonine, a potent efflux inhibitor to circumvent anthracycline resistance in vivo. Genne, P., Dimanche-Boitrel, M.T., Mauvernay, R.Y., Gutierrez, G., Duchamp, O., Petit, J.M., Martin, F., Chauffert, B. Cancer Res. (1992) [Pubmed]
  2. Comparative effects of quinine and cinchonine in reversing multidrug resistance on human leukemic cell line K562/ADM. Genne, P., Duchamp, O., Solary, E., Pinard, D., Belon, J.P., Dimanche-Boitrel, M.T., Chauffert, B. Leukemia (1994) [Pubmed]
  3. Combination of quinine, quinidine and cinchonine for the treatment of acute falciparum malaria: correlation with the susceptibility of Plasmodium falciparum to the cinchona alkaloids in vitro. Sowunmi, A., Salako, L.A., Laoye, O.J., Aderounmu, A.F. Trans. R. Soc. Trop. Med. Hyg. (1990) [Pubmed]
  4. The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum. Diezi, S., Ferri, D., Vargas, A., Mallat, T., Baiker, A. J. Am. Chem. Soc. (2006) [Pubmed]
  5. The enantioselective synthesis of alpha-amino acid derivatives via organoboranes. O'Donnell, M.J., Drew, M.D., Cooper, J.T., Delgado, F., Zhou, C. J. Am. Chem. Soc. (2002) [Pubmed]
  6. Phase I study of cinchonine, a multidrug resistance reversing agent, combined with the CHVP regimen in relapsed and refractory lymphoproliferative syndromes. Solary, E., Mannone, L., Moreau, D., Caillot, D., Casasnovas, R.O., Guy, H., Grandjean, M., Wolf, J.E., André, F., Fenaux, P., Canal, P., Chauffert, B., Wotawa, A., Bayssas, M., Genne, P. Leukemia (2000) [Pubmed]
  7. Intrarectal Quinimax (an association of Cinchona alkaloids) for the treatment of Plasmodium falciparum malaria in children in Niger: efficacy and pharmacokinetics. Barennes, H., Kahiatani, F., Pussard, E., Clavier, F., Meynard, D., Njifountawouo, S., Verdier, F. Trans. R. Soc. Trop. Med. Hyg. (1995) [Pubmed]
  8. The inhibitory effect of cinchonine on human platelet aggregation due to blockade of calcium influx. Shah, B.H., Nawaz, Z., Virani, S.S., Ali, I.Q., Saeed, S.A., Gilani, A.H. Biochem. Pharmacol. (1998) [Pubmed]
  9. Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts. Park, E.J., Kim, M.H., Kim, D.Y. J. Org. Chem. (2004) [Pubmed]
  10. Effect of quinine and cinchonine on human neutrophils functions in vitro. el Benna, J., Labro, M.T. J. Antimicrob. Chemother. (1990) [Pubmed]
  11. Cinchonine per os: efficient circumvention of P-glycoprotein-mediated multidrug resistance. Genne, P., Duchamp, O., Solary, E., Magnette, J., Belon, J.P., Chauffert, B. Anticancer Drug Des. (1995) [Pubmed]
  12. The chemical and immunoglobulin structural features necessary for reactions of quinine-dependent antibodies to neutrophils. Stroncek, D.F., Herr, G.P. Transfusion (1995) [Pubmed]
  13. Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. Furusawa, S., Nakano, S., Wu, J., Sakaguchi, S., Takayanagi, M., Sasaki, K.I., Satoh, S. J. Pharm. Pharmacol. (2001) [Pubmed]
  14. An in situ attenuated total reflection infrared study of a chiral catalytic solid-liquid interface: cinchonidine adsorption on pt. Ferri, D., Bürgi, T. J. Am. Chem. Soc. (2001) [Pubmed]
  15. Activity of a combination of three cinchona bark alkaloids against Plasmodium falciparum in vitro. Druilhe, P., Brandicourt, O., Chongsuphajaisiddhi, T., Berthe, J. Antimicrob. Agents Chemother. (1988) [Pubmed]
  16. Enhanced choline and Rb+ transport in human erythrocytes infected with the malaria parasite Plasmodium falciparum. Kirk, K., Wong, H.Y., Elford, B.C., Newbold, C.I., Ellory, J.C. Biochem. J. (1991) [Pubmed]
  17. Observation of high enantioselectivity for the gas phase hydrogenation of methyl pyruvate using supported Pt catalysts pre-modified with cinchonidine. von Arx, M., Dummer, N., Willock, D.J., Taylor, S.H., Wells, R.P., Wells, P.B., Hutchings, G.J. Chem. Commun. (Camb.) (2003) [Pubmed]
  18. Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone. Röper, S., Franz, M.H., Wartchow, R., Hoffmann, H.M. J. Org. Chem. (2003) [Pubmed]
  19. Michael reactions carried out using a bench-top flow system. Bonfils, F., Cazaux, I., Hodge, P., Caze, C. Org. Biomol. Chem. (2006) [Pubmed]
  20. Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers. Ogawa, T., Hoshina, K., Haginaka, J., Honda, C., Tanimoto, T., Uchida, T. Journal of pharmaceutical sciences. (2005) [Pubmed]
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