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Chemical Compound Review

atabrine     N'-(6-chloro-2-methoxy- acridin-9-yl)-N,N...

Synonyms: Akrichin, Atebrine, Italchin, Metochin, acrichine, ...
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Disease relevance of quinacrine


Psychiatry related information on quinacrine

  • Because quinacrine and chlorpromazine have been used in humans for many years as antimalarial and antipsychotic drugs, respectively, and are known to pass the blood-brain barrier, we suggest that they are immediate candidates for the treatment of Creutzfeldt-Jakob disease and other prion diseases [5].
  • Furthermore, neither LHRH-induced LH release from preprimed tissue nor Ca(2+)-induced LH release were attenuated by quinacrine, indicating that this inhibitor does not interfere with the general Ca(2+)-dependent secretory apparatus of the gonadotroph and that the critical period for its action is in the induction of priming [6].
  • Recovery of the hypoxia-exposed mice to a normal rhythm in T(b), motor activity and feeding was unaffected by mepacrine, a phospholipase A(2) blocker [7].

High impact information on quinacrine


Chemical compound and disease context of quinacrine

  • Medical methods include instillation of antineoplastic agents, antimicrobial agents, or colloidal radioisotopes into the pleural space; quinacrine and tetracycline are moderately to highly effective agents, but the toxicity of the former is substantial [13].
  • We report that quinacrine, chloroquine, and structurally related compounds completely inhibit the antiapoptotic effect of CpG-ODN on WEHI 231 murine B lymphoma cells and inhibit CpG-ODN-induced secretion of IL-6 by WEHI 231 [14].
  • Activation of wild-type as well as F347A, D100N or K333M/K334T/R335L CCK2 receptors by this ligand led to a similar arachidonic acid release which was blocked by pertussis toxin and the phospholipase A2 inhibitor, mepacrine [15].
  • METHODS--Forty patients with carcinoma and pleural effusions refractory to repeated pleural aspirations over the previous 12 weeks were randomised to receive treatment with intrathoracic instillation of mepacrine or bleomycin [16].
  • Activity of picolinic acid in combination with the antiprotozoal drug quinacrine against Mycobacterium avium complex [17].

Biological context of quinacrine


Anatomical context of quinacrine

  • The compound ATP gamma S inhibits agonist-stimulated adenylate cyclase activity in solubilized and in isobutylmethylxanthine (IBMX) and quinacrine pretreated membranes, suggesting that ATP gamma S inhibition occurs independent of AVP and A1 adenosine receptors and of phospholipase A2 activity [23].
  • BK also stimulates the synthesis of PGE2 in rabbit ileal and colonic mucosa and this effect can be blocked by prior addition of either indomethacin or mepacrine [24].
  • Treatment with SC41930 significantly reduced, whereas either WEB2086 or quinacrine completely abolished, the increased leukocyte adherence and emigration induced by L-NAME [25].
  • Labeling the vacuole with either quinacrine or FITC-dextran revealed vacuole fragmentation that was not found in untreated cells or in cells arrested in G2 by unrelated means [26].
  • In support of this hypothesis, the distribution of methylaminoisobutyrate between plasma membrane vesicles and their supporting media was influenced in the predictable way by NADH, quinacrine, and an uncoupling agent, proceeding on the assumption that more of the vesicles had the everted rather than the natural orientation [27].

Associations of quinacrine with other chemical compounds

  • In vitro drug testing showed that (a) W.B.'s organisms were not more drug resistant than three other isolates and that (b) W.B.'s organisms were more sensitive to combined quinacrine and metronidazole than to either drug alone [3].
  • 4. Second, the antral uptake of the fluorescent cyclic amine, quinacrine, from the gastric lumen of pylorus-ligated rats was monitored by fluorescent microscopy and spectrophotometry and was demonstrated to be inhibited in a step-wise fashion as the luminal pH was decreased [28].
  • Instead, we have found that muscarinic or histamine H1 receptor stimulation elicits the release of arachidonic acid through a quinacrine-sensitive mechanism, possibly phospholipase A2 [29].
  • Mepacrine (quinacrine) and hydrocortisone inhibited and a phorbol ester enhanced both chemotaxis and phospholipase A2 activity [30].
  • Eicosatetraynoic acid, an inhibitor of lipoxygenase and cyclooxygenase, and quinacrine, an inhibitor of phospholipase, prevented and reversed acetylcholine-induced relaxation, respectively, and inhibited acetylcholine-induced increased levels of cGMP [31].
  • Although doxorubicin failed to induce TP53 expression or functional activity, quinacrine induced TP53 mRNA and protein expression, increased TP53 reporter activity and p21 protein expression, and induced growth inhibition in these wild-type TP53 cell lines [32].

Gene context of quinacrine

  • Interruption of the yeast gene, denoted as VMA8, resulted in the null mutant delta vma8::URA3 that, like all the other V-ATPase null mutants, did not grow on medium buffered at pH 7.5 and showed no accumulation of quinacrine into their vacuoles [33].
  • By screening based on these phenotypes and the inability of vma mutants to accumulate the lysosomotropic dye quinacrine in their vacuoles, five new vma complementation groups (vma41 to vma45) were identified [34].
  • However, no defect in vacuolar acidification is apparent from quinacrine staining, and Gef1p co-localizes with Mnt1p in the medial Golgi [35].
  • Monocyte Chemotactic Protein-1 (MCP-1), a member of the Cys-Cys branch of the chemokine superfamily, induced a mepacrine- and manoalide-sensitive increase in the release of [3H]arachidonic acid from prelabeled human monocytes and monocytic THP-1 leukemic cells [36].
  • PMA elicited an inhibitory effect on PDE4D5 activity in HASMC treated with the cyclooxygenase (COX) inhibitor indomethacin, the COX-2 selective inhibitor NS-398, the phospholipase A(2) inhibitor quinacrine, and the cAMP-dependent protein kinase A (PKA) inhibitor H89 [37].

Analytical, diagnostic and therapeutic context of quinacrine

  • The increased immunogenicity of L1210Ha leukemia occurring at the first transplant generation of DTIC-treated histocompatible (BALB/cCr x DBA/2Cr)F1 male mice or the appearance of strong lymphoma-associated transplantation antigens at transplant generation 6 was prevented by simultaneous administration of quinacrine [38].
  • A recessive nuclear mutation, vph1-1, caused an abnormally high vacuolar pH of 6.9, as assayed by flow cytometry, and eliminated vacuolar uptake of the weak base quinacrine [39].
  • Methaphase chromosomes from karyotypically normal adult humans (three males, six females) and one male with a 13p - chromosome were stained by quinacrine and then by the Ag-AS silver staining method to reveal nucleolus organizer regions (NORs) [40].
  • The streptavidine-horseradish-peroxidase and DAB detection system used permitted the unequivocal identification of sperm heads with zero, one, or two hybridization signals and proved superior to either quinacrine staining or radioactive in situ hybridization [41].
  • Both mutants had prolonged bleeding times accompanied by abnormalities of dense granules as determined by whole mount electron microscopy of platelets and by labeling platelets with mepacrine [42].


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  2. Quinacrine ochronosis. Tuffanelli, D.L. JAMA (1976) [Pubmed]
  3. Chronic giardiasis: studies on drug sensitivity, toxin production, and host immune response. Smith, P.D., Gillin, F.D., Spira, W.M., Nash, T.E. Gastroenterology (1982) [Pubmed]
  4. 31,781 cases of non-surgical female sterilisation with quinacrine pellets in Vietnam. Hieu, D.T., Tan, T.T., Tan, D.N., Nguyet, P.T., Than, P., Vinh, D.Q. Lancet (1993) [Pubmed]
  5. Acridine and phenothiazine derivatives as pharmacotherapeutics for prion disease. Korth, C., May, B.C., Cohen, F.E., Prusiner, S.B. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  6. Evidence for a role of phospholipase A2 in the mechanism of LHRH priming in rat anterior pituitary tissue. Thomson, F.J., Johnson, M.S., Mitchell, R., Wolbers, B. J. Endocrinol. (1994) [Pubmed]
  7. Hypoxia-induced sickness behaviour. Kozak, W., Wrotek, S., Walentynowicz, K. J. Physiol. Pharmacol. (2006) [Pubmed]
  8. Arachidonic acid metabolites as mediators of somatostatin-induced increase of neuronal M-current. Schweitzer, P., Madamba, S., Siggins, G.R. Nature (1990) [Pubmed]
  9. Y chromosome visibility in quinacrine-stained human spermatozoa. Roberts, A.M., Goodall, H. Nature (1976) [Pubmed]
  10. Quinacrine ochronosis and rheumatoid arthritis. Egorin, M.J., Trump, D.L., Wainwright, C.W. JAMA (1976) [Pubmed]
  11. CD18/ICAM-1-dependent oxidative NF-kappaB activation leading to nitric oxide production in rat Kupffer cells cocultured with syngeneic hepatoma cells. Kurose, I., Saito, H., Miura, S., Ebinuma, H., Higuchi, H., Watanabe, N., Zeki, S., Nakamura, T., Takaishi, M., Ishii, H. J. Clin. Invest. (1997) [Pubmed]
  12. Endothelin's biphasic effect on fluid absorption in the proximal straight tubule and its inhibitory cascade. Garcia, N.H., Garvin, J.L. J. Clin. Invest. (1994) [Pubmed]
  13. Pleural effusion from malignancy. Leff, A., Hopewell, P.C., Costello, J. Ann. Intern. Med. (1978) [Pubmed]
  14. Antagonism of immunostimulatory CpG-oligodeoxynucleotides by quinacrine, chloroquine, and structurally related compounds. Macfarlane, D.E., Manzel, L. J. Immunol. (1998) [Pubmed]
  15. Further evidence that the CCK2 receptor is coupled to two transduction pathways using site-directed mutagenesis. Pommier, B., Marie-Claire, C., Da Nascimento, S., Wang, H.L., Roques, B.P., Noble, F. J. Neurochem. (2003) [Pubmed]
  16. Chemical pleurodesis in malignant pleural effusions: a randomised prospective study of mepacrine versus bleomycin. Koldsland, S., Svennevig, J.L., Lehne, G., Johnson, E. Thorax (1993) [Pubmed]
  17. Activity of picolinic acid in combination with the antiprotozoal drug quinacrine against Mycobacterium avium complex. Shimizu, T., Tomioka, H. Antimicrob. Agents Chemother. (2006) [Pubmed]
  18. Reproducible chromosome changes of polycyclic hydrocarbon-induced rat leukemia: incidence and chromosome banding pattern. Sugiyama, T., Uenaka, H., Ueda, N., Fukuhara, S., Maeda, S. J. Natl. Cancer Inst. (1978) [Pubmed]
  19. Role of prostaglandins and calcium in the effects of Entamoeba histolytica on colonic electrolyte transport. McGowan, K., Piver, G., Stoff, J.S., Donowitz, M. Gastroenterology (1990) [Pubmed]
  20. Transformation and motility of human platelets: details of the shape change and release reaction observed by optical and electron microscopy. Allen, R.D., Zacharski, L.R., Widirstky, S.T., Rosenstein, R., Zaitlin, L.M., Burgess, D.R. J. Cell Biol. (1979) [Pubmed]
  21. Stimulation of tubulin tyrosinolation in rabbit leukocytes evoked by the chemoattractant formyl-methionyl-leucyl-phenylalanine. Nath, J., Flavin, M., Schiffmann, E. J. Cell Biol. (1981) [Pubmed]
  22. Structural effects of quinacrine binding in the open channel of the acetylcholine receptor. Yu, Y., Shi, L., Karlin, A. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  23. ATP receptor regulation of adenylate cyclase and protein kinase C activity in cultured renal LLC-PK1 cells. Anderson, R.J., Breckon, R., Dixon, B.S. J. Clin. Invest. (1991) [Pubmed]
  24. Bradykinin-stimulated electrolyte secretion in rabbit and guinea pig intestine. Involvement of arachidonic acid metabolites. Musch, M.W., Kachur, J.F., Miller, R.J., Field, M., Stoff, J.S. J. Clin. Invest. (1983) [Pubmed]
  25. Mediators of leukocyte adhesion in rat mesenteric venules elicited by inhibition of nitric oxide synthesis. Arndt, H., Russell, J.B., Kurose, I., Kubes, P., Granger, D.N. Gastroenterology (1993) [Pubmed]
  26. Yeast vacuoles fragment when microtubules are disrupted. Guthrie, B.A., Wickner, W. J. Cell Biol. (1988) [Pubmed]
  27. Unexpected additional mode of energization of amino-acid transport into Ehrlich cells. Garcia-Sancho, J., Sanchez, A., Handlogten, M.E., Christensen, H.N. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  28. Amine trapping: physical explanation for the inhibitory effect of gastric acidity on the postprandial release of gastrin. Studies on rats and dogs. Lichtenberger, L.M., Nelson, A.A., Graziani, L.A. Gastroenterology (1986) [Pubmed]
  29. Neurotransmitter receptors mediate cyclic GMP formation by involvement of arachidonic acid and lipoxygenase. Snider, R.M., McKinney, M., Forray, C., Richelson, E. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  30. Chemoattractants stimulate degradation of methylated phospholipids and release of arachidonic acid in rabbit leukocytes. Hirata, F., Corcoran, B.A., Venkatasubramanian, K., Schiffmann, E., Axelrod, J. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  31. Agonist-induced endothelium-dependent relaxation in rat thoracic aorta may be mediated through cGMP. Rapoport, R.M., Murad, F. Circ. Res. (1983) [Pubmed]
  32. Deficient TP53 expression, function, and cisplatin sensitivity are restored by quinacrine in head and neck cancer. Friedman, J., Nottingham, L., Duggal, P., Pernas, F.G., Yan, B., Yang, X.P., Chen, Z., Van Waes, C. Clin. Cancer Res. (2007) [Pubmed]
  33. A bovine cDNA and a yeast gene (VMA8) encoding the subunit D of the vacuolar H(+)-ATPase. Nelson, H., Mandiyan, S., Nelson, N. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  34. Mutations in the yeast KEX2 gene cause a Vma(-)-like phenotype: a possible role for the Kex2 endoprotease in vacuolar acidification. Oluwatosin, Y.E., Kane, P.M. Mol. Cell. Biol. (1998) [Pubmed]
  35. Golgi localization and functionally important domains in the NH2 and COOH terminus of the yeast CLC putative chloride channel Gef1p. Schwappach, B., Stobrawa, S., Hechenberger, M., Steinmeyer, K., Jentsch, T.J. J. Biol. Chem. (1998) [Pubmed]
  36. Rapid induction of arachidonic acid release by monocyte chemotactic protein-1 and related chemokines. Role of Ca2+ influx, synergism with platelet-activating factor and significance for chemotaxis. Locati, M., Zhou, D., Luini, W., Evangelista, V., Mantovani, A., Sozzani, S. J. Biol. Chem. (1994) [Pubmed]
  37. Phorbol 12-myristate 13-acetate triggers the protein kinase A-mediated phosphorylation and activation of the PDE4D5 cAMP phosphodiesterase in human aortic smooth muscle cells through a route involving extracellular signal regulated kinase (ERK). Baillie, G., MacKenzie, S.J., Houslay, M.D. Mol. Pharmacol. (2001) [Pubmed]
  38. Drug-mediated antigenic changes in murine leukemia cells: antagonistic effects of quinacrine, an antimutagenic compound. Giampietri, A., Fioretti, M.C., Goldin, A., Bonmassar, E. J. Natl. Cancer Inst. (1980) [Pubmed]
  39. Assay of vacuolar pH in yeast and identification of acidification-defective mutants. Preston, R.A., Murphy, R.F., Jones, E.W. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  40. Frequency of satellite association of human chromosomes is correlated with amount of Ag-staining of the nucleolus organizer region. Miller, D.A., Tantravahi, R., Dev, V.G., Miller, O.J. Am. J. Hum. Genet. (1977) [Pubmed]
  41. Determination of Y chromosome aneuploidy in human sperm nuclei by nonradioactive in situ hybridization. Guttenbach, M., Schmid, M. Am. J. Hum. Genet. (1990) [Pubmed]
  42. Platelet storage pool deficiency associated with inherited abnormalities of the inner ear in the mouse pigment mutants muted and mocha. Swank, R.T., Reddington, M., Howlett, O., Novak, E.K. Blood (1991) [Pubmed]
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