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Chemical Compound Review

Phenasal     5-chloro-N-(2-chloro-4-nitro- phenyl)-2...

Synonyms: Cestocid, Devermin, Radewerm, Fenasal, Niclocide, ...
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Disease relevance of niclosamide


High impact information on niclosamide

  • Further studies revealed that HR325 reduced intracellular ATP levels by uncoupling oxidative phosphorylation, albeit with a 1000-fold lower potency than the antihelmintic drug niclosamide [5].
  • The investigation of the niclosamide-DNA interaction using an electrochemical DNA-biosensor showed for the first time clear evidence of interaction with DNA and suggested that niclosamide toxicity can be caused by this interaction, after reductive activation [4].
  • The detection limit was found to be 2.05 x 10(-8) mol dm(-3) niclosamide [6].
  • Potent inhibitors of CYP1A2 were artemisinin, dihydroartemisinin, thiabendazole, primaquine, and niclosamide (K(i) = 0.43, 3.67, 1.54, 0.22, and 2.70 microM, respectively) [7].
  • The subjects assigned to the niclosamide-treated group were comparable with those in the placebo group in age (27.2 versus 27.8 years), total water contact (101.9 versus 109.0 hr), lotion application compliance (93.5% versus 90.6%), and avoidance of whole body water contact (94.7% versus 96.7%) [8].

Chemical compound and disease context of niclosamide


Biological context of niclosamide


Anatomical context of niclosamide

  • The subjects applying the niclosamide lotion were comparable to those applying placebo lotion in age (mean 30 years for both), total water contact (184.5 hr versus 173.8 hr), reported lotion application compliance (88% versus 92%), and reported water contact involving skin exposure other than upper and lower limbs (23% versus 27%) [19].
  • Susceptibility to genotoxic effects of niclosamide in human peripheral lymphocytes exposed in vitro and in vivo [18].
  • The niclosamide group revealed epithelial necrosis in the digestive glands and the gonads [20].
  • 3. During 4-h tests, Malpighian tubules of the chironomid actively transported Bayer 73 and TFM in vitro, and on a per tubule basis, more TFM was transported than Bayer 73 [21].
  • Niclosamide at 160 mg/kg given as single or 2 doses 3 days apart was 91.1% and 92.6% effective, respectively, against the parasites in the small intestine [22].

Associations of niclosamide with other chemical compounds


Gene context of niclosamide

  • Its effects on mouse-sperm morphology were evaluated in CD1 and (BALB/cJ x DBA/2J) F1 mice after 5 daily oral niclosamide doses of either 60, 80, 100 or 120 mg/kg [27].
  • A randomized, double-blind, placebo-controlled field trial of a topical antipenetrant lotion, 1% niclosamide, applied daily to the upper and lower limbs of farmers occupationally exposed to Schistosoma mansoni cercarial-infested water, was conducted in the Nile Delta to assess its safety and efficacy in preventing reinfection [19].
  • 2. Toxicant residues were widely distributed during early hours of exposure, but later and during a 24-h post-exposure period, they became concentrated in the trunk and intestinal tract; the posterior movement of Bayer 73 was more rapid than that of TFM [21].
  • The most promising compound was the pyridothienotriazine 12k, with activity similar to that of the salicylanilides niclosamide and oxiclozanide (MLC 0.8 mg l(-1) in PBS, 1.5 mg l(-1) in seawater; MLC = minimum 24 h lethal concentration) [28].
  • The anemia resolved within days under therapy with niclosamide and temporary vitamin B12 supplements [29].

Analytical, diagnostic and therapeutic context of niclosamide


  1. Niclosamide therapy for tapeworm infections. Pearson, R.D., Hewlett, E.L. Ann. Intern. Med. (1985) [Pubmed]
  2. Inhibition of severe acute respiratory syndrome coronavirus replication by niclosamide. Wu, C.J., Jan, J.T., Chen, C.M., Hsieh, H.P., Hwang, D.R., Liu, H.W., Liu, C.Y., Huang, H.W., Chen, S.C., Hong, C.F., Lin, R.K., Chao, Y.S., Hsu, J.T. Antimicrob. Agents Chemother. (2004) [Pubmed]
  3. Anthelmintics. Current concepts in the treatment of helminthic infections. Katz, M. Drugs (1986) [Pubmed]
  4. Detection of the damage caused to DNA by niclosamide using an electrochemical DNA-biosensor. Abreu, F.C., Goulart, M.O., Brett, A.M. Biosensors & bioelectronics. (2002) [Pubmed]
  5. Inhibition of stimulated Jurkat cell adenosine 3',5'-cyclic monophosphate synthesis by the immunomodulatory compound HR325. Curnock, A.P., Thomson, T.A., Westwood, R., Kuo, E.A., Williamson, R.A., Yea, C.M., Ruuthb, E. Biochem. Pharmacol. (2001) [Pubmed]
  6. Voltammetric determination of niclosamide at a glassy carbon electrode. Alemu, H., Wagana, P., Tseki, P.F. The Analyst. (2002) [Pubmed]
  7. Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Bapiro, T.E., Egnell, A.C., Hasler, J.A., Masimirembwa, C.M. Drug Metab. Dispos. (2001) [Pubmed]
  8. Evaluation of a twice-a-week application of 1% niclosamide lotion in preventing Schistosoma haematobium reinfection. Podgore, J.K., Abu-Elyazeed, R.R., Mansour, N.S., Youssef, F.G., Hibbs, R.G., Gere, J.A. Am. J. Trop. Med. Hyg. (1994) [Pubmed]
  9. Mutagenic activity of 2-chloro-4-nitroaniline and 5-chlorosalicylic acid in Salmonella typhimurium: two possible metabolites of niclosamide. Espinosa-Aguirre, J.J., Reyes, R.E., Cortinas de Nava, C. Mutat. Res. (1991) [Pubmed]
  10. Studies on the mechanism of potentiation of the acute toxicity of 2,4-D n-butyl ester and 2',5-dichloro-4'-nitrosalicylanilide in rainbow trout by carbaryl. Statham, C.N., Lech, J.J. Toxicol. Appl. Pharmacol. (1976) [Pubmed]
  11. Mepacrine therapy in niclosamide resistant taeniasis. Koul, P.A., Wahid, A., Bhat, M.H., Wani, J.I., Sofi, B.A. The Journal of the Association of Physicians of India. (2000) [Pubmed]
  12. Cestodes. Gemmell, M.A., Johnstone, P.D. Antibiotics and chemotherapy. (1981) [Pubmed]
  13. The treatment of fasciolopsiasis with niclosamide and dichlorophen. Idris, M., Rahman, K.M., Muttalib, M.A., Azad Khan, A.K. The Journal of tropical medicine and hygiene. (1980) [Pubmed]
  14. Extractive alkylation of 5,2'-dichloro-4'-nitrosalicylanilide (niclosamide) for gas-liquid chromatographic analysis. Churchill, F.C., Ku, D.N. J. Chromatogr. (1980) [Pubmed]
  15. Energy metabolism in Cotugnia digonopora and the effect of anthelmintics. Pampori, N.A., Singh, G., Srivastava, V.M. Mol. Biochem. Parasitol. (1984) [Pubmed]
  16. Genotoxic effects of niclosamide in Aspergillus nidulans. de la Torre, R.A., de la Rúa Barceló, R., Hernández, G., Espinosa, J.J., Cortinas de Nava, C. Mutat. Res. (1989) [Pubmed]
  17. Mutagenicity of antiamebic and anthelmintic drugs in the Salmonella typhimurium microsomal test system. Cortinas de Nava, C., Espinosa, J., García, L., Zapata, A.M., Martínez, E. Mutat. Res. (1983) [Pubmed]
  18. Susceptibility to genotoxic effects of niclosamide in human peripheral lymphocytes exposed in vitro and in vivo. Ostrosky-Wegman, P., García, G., Montero, R., Pérez Romero, B., Alvarez Chacón, R., Cortinas de Nava, C. Mutat. Res. (1986) [Pubmed]
  19. Field trial of 1% niclosamide as a topical antipenetrant to Schistosoma mansoni cercariae. Abu-Elyazeed, R.R., Podgore, J.K., Mansour, N.S., Kilpatrick, M.E. Am. J. Trop. Med. Hyg. (1993) [Pubmed]
  20. The development of tissue lesions in the snail Lymnaea glabra exposed to a sublethal dose of molluscicide. Rondelaud, D., Dreyfuss, G. Vet. Res. (1996) [Pubmed]
  21. Whole-body distribution an Malpighian tubule transport of 2',5-dichloro-4'-nitrosalicylanilide (Bayer 73) and 3-trifluoromethyl-4-nitrophenol in larvae of the aquatic midge Chironomus tentans. Hansen, C.R., Gauss, J.D., Kawatski, J.A. Xenobiotica (1980) [Pubmed]
  22. Chemotherapy of paramphistomosis in cattle. Rolfe, P.F., Boray, J.C. Aust. Vet. J. (1987) [Pubmed]
  23. Preliminary trials against Biomphalaria glabrata of a new molluscicide formulation: geletin granules containing Bayluscide wettable powder. Upatham, E.S., Sturrock, R.F. Ann. Trop. Med. Parasitol. (1977) [Pubmed]
  24. Comparative effects of uredofos, niclosamide, and bunamidine hydrochloride against tapeworm infections in dogs. Roberson, E.L. Am. J. Vet. Res. (1976) [Pubmed]
  25. Treatment of fish parasites. 2. Effects of praziquantel, niclosamide, levamisole-HCl, and metrifonate on monogenea (Gyrodactylus aculeati, Diplozoon paradoxum). Schmahl, G., Taraschewski, H. Parasitol. Res. (1987) [Pubmed]
  26. Hymenolepis diminuta: catalysis of transmembrane proton translocation by mitochondrial NADPH-->NAD transhydrogenase. Mercer, N.A., McKelvey, J.R., Fioravanti, C.F. Exp. Parasitol. (1999) [Pubmed]
  27. Sperm shape abnormality and urine mutagenicity in mice treated with niclosamide. Vega, S.G., Guzmán, P., García, L., Espinosa, J., Cortinas de Nava, C. Mutat. Res. (1988) [Pubmed]
  28. In vitro efficacy of new antiprotozoals against Philasterides dicentrarchi (Ciliophora, Scuticociliatida). Paramá, A., Iglesias, R., Alvarez, F., Leiro, J.M., Quintela, J.M., Peinador, C., González, L., Riguera, R., Sanmartín, M.L. Dis. Aquat. Org. (2004) [Pubmed]
  29. Case of megaloblastic anemia caused by intestinal taeniasis. Vuylsteke, P., Bertrand, C., Verhoef, G.E., Vandenberghe, P. Ann. Hematol. (2004) [Pubmed]
  30. The USAID/Government of Egypt's Schistosomiasis Research Project (SRP). El Khoby, T., Galal, N., Fenwick, A. Parasitol. Today (Regul. Ed.) (1998) [Pubmed]
  31. Epidemiology of taeniasis and cysticercosis in a Peruvian village. The Cysticercosis Working Group in Peru. Diaz, F., Garcia, H.H., Gilman, R.H., Gonzales, A.E., Castro, M., Tsang, V.C., Pilcher, J.B., Vasquez, L.E., Lescano, M., Carcamo, C. Am. J. Epidemiol. (1992) [Pubmed]
  32. Epidemiology and control of schistosomiasis mansoni in communities living on the Cuando River floodplain of East Caprivi, Namibia. Schutte, C.H., Evans, A.C., Pammenter, M.D., Cooppan, R.M., Pretorius, S.J., Joubert, P.H., Gouws, E., Jooste, P.L., Badenhorst, C.J., Joubert, J.J. Ann. Trop. Med. Parasitol. (1995) [Pubmed]
  33. Taeniacidal efficacy of SQ 21,704 in dogs by various types of oral administration and in comparison with niclosamide and bunamidine hydrochloride. Cruthers, L.R., Linkenheimer, W.H., Maplesden, D.C. Am. J. Vet. Res. (1979) [Pubmed]
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