A review on the pharmacokinetic properties and toxicity considerations for chloroquine and hydroxychloroquine to potentially treat coronavirus patients |
Askarian, Fatemeh
(Student Research Committee, Faculty of Pharmacy, Kerman University of Medical Sciences)
Firoozi, Zahra (Department of Medical Genetics, School of Medicine, Kerman University of Medical Sciences) Ebadollahi‑Natanzi, Alireza (Medicinal Plants Department, Imam Khomeini Higher Education Center, Agricultural Research, Education and Extension Organization (AREEO)) Bahrami, Solmaz (Department of Institutional Research, Westclif University) Rahimi, Hamid‑Reza (Student Research Committee, Faculty of Pharmacy, Kerman University of Medical Sciences) |
1 | Schaer CA, Laczko E, Schoedon G, Schaer DJ, Vallelian F (2013) Chloroquine interference with hemoglobin endocytic trafficking suppresses adaptive heme and iron homeostasis in macrophages: the paradox of an antimalarial agent. Oxid Med Cell Longev 2013:870472. https://doi.org/10.1155/2013/870472 DOI |
2 | Singhi S, Singhi P, Singh M (1979) Extrapyrbmidal syndrome following chloroquine therapy. Indian J Pediatr 46:58-60. https://doi.org/10.1007/BF02811499 DOI |
3 | Wang C, Fortin P, Li Y, Panaritis T, Gans M, Esdaile J (1999) Discontinuation of antimalarial drugs in systemic lupus erythematosus. J Rheumatol 26:808-815.PMID: 10229401 |
4 | Seckin U, Ozoran K, Ikinciogullari A, Borman P, Bostan EE (2000) Hydroxychloroquineototoxicity in a patient with rheumatoid arthritis. Rheumatol Int 19:203-204. https://doi.org/10.1007/s002960000054 DOI |
5 | Raoult D, Houpikian P, Dupont HT, Riss JM, Arditi-Djiane J, Brouqui P (1999) Treatment of Q fever endocarditis: comparison of 2 regimens containing doxycycline and ofloxacin or hydroxychloroquine. Arch Intern Med 159:167-173. https://doi.org/10.1001/archi nte.159.2.167 DOI |
6 | Boulos A, Rolain J-M, Raoult D (2004) Antibiotic susceptibility of Tropheryma whipplei in MRC5 cells. Antimicrob Agents Chemother 48:747-752. https://doi.org/10.1128/AAC.48.3.747-752.2004 DOI |
7 | Savarino A, Lucia MB, Rastrelli E, Rutella S, Golotta C, Morra E et al (2004) Anti-HIV effects of chloroquine: inhibition of viral particle glycosylation and synergism with protease inhibitors. J Acquir Immune Defic Syndr 35:223-232. https://doi.org/10.1097/00126334-200403010-00002 DOI |
8 | Vandekerckhove S, D'hooghe M (2015) Quinoline-based antimalarial hybrid compounds. Bioorg Med Chem 23:5098-5119. https://doi.org/10.1016/j.bmc.2014.12.018 DOI |
9 | Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG et al (2005) Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virol J 2:69 https://doi.org/10.1186/1743-422X-2-69 DOI |
10 | Devaux CA, Rolain J-M, Colson P, Raoult D (2020) New insights on the antiviral effects of chloroquine against coronavirus: what to expect for COVID-19? Int J Antimicrob Agents 55:105938. https://doi.org/10.1016/j. ijant imicag.2020.105938 DOI |
11 | McChesney EW (1983) Animal toxicity and pharmacokinetics of hydroxychloroquine sulfate. Am J Med 75:11-18. https://doi.org/10.1016/0002-9343(83)91265-2 DOI |
12 | Yogasundaram H, Hung W, Paterson ID, Sergi C, Oudit GY (2018) Chloroquine-induced cardiomyopathy: a reversible cause of heart failure. ESC Heart Fail 5:372-375. https://doi.org/10.1002/ehf2.12276 DOI |
13 | Yam J, Kwok A (2006) Ocular toxicity of hydroxychloroquine. Hong Kong Med J 12:294. PMID: 16912357 |
14 | Marmor MF, Kellner U, Lai TY, Lyons JS, Mieler WF (2011) Revised recommendations on screening for chloroquine and hydroxychloroquine retinopathy. Ophthalmology 118:415-422. https://doi.org/10.1016/j.ophtha.2010.11.017 DOI |
15 | Pukrittayakamee S, Tarning J, Jittamala P, Charunwatthana P, Lawpoolsri S, Lee SJ et al (2014) Pharmacokinetic interactions between primaquine and chloroquine. Antimicrob Agents Chemother 58:3354-3359. https://doi.org/10.1128/AAC.02794-13 DOI |
16 | Olatunde Farombi E, Shyntum YY, Emerole GO (2003) Influence of chloroquine treatment and Plasmodium falciparum malaria infection on some enzymatic and non-enzymatic antioxidant defense indices in humans. Drug Chem Toxicol 26:59-71. https://doi.org/10.1081/DCT-120017558 DOI |
17 | Omotosho O, Adebiyi M, Oyeyemi M (2014) Comparative study of the haematology and serum biochemistry of male wistar rats treated with chloroquine and artesunate. J Physiol Pharmacol Adv 4:413-419. https://doi.org/10.5455/jppa.20140827112119 DOI |
18 | Powrie J, Smith G, Shojaee-Moradie F, Sonksen P, Jones R (1991) Mode of action of chloroquine in patients with noninsulin-dependent diabetes mellitus. Am J Physiol Endocrinol Metab 260:E897-E904. https://doi.org/10.1152/ajpendo.1991.260.6E897 DOI |
19 | Yogasundaram H, Putko BN, Tien J, Paterson DI, Cujec B, Ringrose J et al (2014) Hydroxychloroquine-induced cardiomyopathy: case report, pathophysiology, diagnosis, and treatment. Can J Cardiol 30:1706-1715. https://doi.org/10.1016/j.cjca.2014.08.016 DOI |
20 | Marmor MF, Kellner U, Lai TY, Melles RB, Mieler WF (2016) Recommendations on screening for chloroquine and hydroxychloroquine retinopathy (2016 revision). Ophthalmology 123:1386-1394. https://doi.org/10.1016/j.ophtha.2016.01.058 DOI |
21 | Han Y, Pham HT, Xu H, Quan Y, Mesplede T (2019) Antimalarial drugs and their metabolites are potent Zika virus inhibitors. J Med Virol 91:1182-1190. https://doi.org/10.1002/jmv.25440 DOI |
22 | Kolars JC, Schmiedlin-Ren P, Schuetz JD, Fang C, Watkins PB (1992) Identification of rifampin-inducible P450IIIA4 (CYP3A4) in human small bowel enterocytes. J Clin Investig 90:1871-1878. https://doi.org/10.1172/JCI116064 DOI |
23 | Thorogood N, Atwal S, Mills W, Jenner M, Lewis D, Cavenagh J et al (2007) The risk of antimalarials in patients with renal failure. Postgrad Med J 83:8. https://doi.org/10.1136/pgmj.2007.063735 DOI |
24 | Mohan D, Mohandas E, Rajat R (1981) Chloroquine psychosis: a chemical psychosis? J Natl Med Assoc 73:1073. PMID: 7310924 |
25 | Ge X-Y, Li J-L, Yang X-L, Chmura AA, Zhu G, Epstein JH et al (2013) Isolation and characterization of a bat SARS-like coronavirus that uses the ACE2 receptor. Nature 503:535-538. https://doi.org/10.1038/nature12711 DOI |
26 | Izmirly PM, Costedoat-Chalumeau N, Pisoni CN, Khamashta MA, Kim MY, Saxena A et al (2012) Maternal use of hydroxychloroquine is associated with a reduced risk of recurrent anti- SSA/Ro-antibody-associated cardiac manifestations of neonatal lupus. Circulation 126:76-82. https://doi.org/10.1161/CIRCULATIONAHA.111.089268 DOI |
27 | Zhao X, Jiang Y, Zhao Y, Xi H, Liu C, Qu F et al (2020) Analysis of the susceptibility to COVID-19 in pregnancy and recommendations on potential drug screening. Eur J Clin Microbiol Infect Dis 23:1-12. https://doi.org/10.1007/s10096-020-03897-6 DOI |
28 | Saghir SAM, AlGabri NA, Alagawany MM, Attia YA, Alyileili SR, Elnesr SS, Shafi ME, Al-shargi OYA, Al-balagi N, Alwajeeh AS, Alsalahi OS, Patra AK, Khafaga AF, Negida A, Noreldin A, Al-Amarat W, Almaiman AA, El-Tarabily KA, Abd El-Hack ME (2021) Chloroquine and hydroxychloroquine for the prevention and treatment of COVID-19: a fiction, hope or hype? An updated review. Ther Clin Risk Manag 17:371-387. https://doi.org/10.2147/TCRM.S301817 DOI |
29 | Wang L-F, Shi Z, Zhang S, Field H, Daszak P, Eaton BT (2006) Review of bats and SARS. Emerg Infect Dis 12:1834. https://doi.org/10.3201/eid1212.060401 DOI |
30 | Wu F, Zhao S, Yu B, Chen Y-M, Wang W, Song Z-G et al (2020) A new coronavirus associated with human respiratory disease in China. Nature 579:265-269. https://doi.org/10.1038/s41586-020-2008-3 DOI |
31 | Wu Z, McGoogan JM (2020) Characteristics of and important lessons from the coronavirus disease 2019 (COVID-19) outbreak in China: summary of a report of 72,314 cases from the Chinese Center for Disease Control and Prevention. JAMA 323(13):1239-1242. https://doi.org/10.1001/jama.2020.2648 DOI |
32 | Organization WH (2020) Coronavirus disease 2019 (COVID-19): situation report. WHO, p 209 |
33 | Hoffmann M, Kleine-Weber H, Schroeder S, Kruger N, Herrler T, Erichsen S et al (2020) SARS-CoV-2 cell entry depends on ACE2 and TMPRSS2 and is blocked by a clinically proven protease inhibitor. Cell 181:271-280.e8. https://doi.org/10.1016/j.cell.2020.02.052 DOI |
34 | Levy JMM, Towers CG, Thorburn A (2017) Targeting autophagy in cancer. Nat Rev Cancer 17:528-542. https://doi.org/10.1038/nrc.2017.53 DOI |
35 | Accapezzato D, Visco V, Francavilla V, Molette C, Donato T, Paroli M et al (2005) Chloroquine enhances human CD8+ T cell responses against soluble antigens in vivo. J Exp Med 202:817-828. https://doi.org/10.1084/jem.20051106 DOI |
36 | Tiberghien F, Loor F (1996) Ranking of P-glycoprotein substrates and inhibitors by a calcein-AM fluorometry screening assay. Anticancer Drugs 7:568-578. https://doi.org/10.1097/00001813-199607000-00012 DOI |
37 | Furst DE (1996) Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases. Lupus 5:S11-S15. PMID: 8803904 DOI |
38 | Ahmed MH, Ashton N, Balment RJ (2003) Renal function in a rat model of analgesic nephropathy: effect of chloroquine. J Pharmacol Exp Ther 305:123-130. https://doi.org/10.1124/jpet.102.047233 DOI |
39 | Xu Z, Shi L, Wang Y, Zhang J, Huang L, Zhang C et al (2020) Pathological findings of COVID-19 associated with acute respiratory distress syndrome. Lancet Respir Med 8:420-422. https://doi.org/10.1016/S2213-2600(20)30076-X DOI |
40 | Huang C, Wang Y, Li X, Ren L, Zhao J, Hu Y et al (2020) Clinical features of patients infected with 2019 novel coronavirus in Wuhan, China. Lancet 395:497-506. https://doi.org/10.1016/S0140-6736(20)30183-5 DOI |
41 | Yang Y-p, Hu L-f, Zheng H-f et al (2013) Application and interpretation of current autophagy inhibitors and activators. Acta Pharmacol Sin 34:625-635. https://doi.org/10.1038/aps.2013.5 DOI |
42 | Liu J, Cao R, Xu M, Wang X, Zhang H, Hu H, Li Y, Hu Z, Zhong W, Wang M (2020) Hydroxychloroquine, a less toxic derivative of chloroquine, is effective in inhibiting SARS-CoV-2 infection in vitro. Cell Discov 6:16. https://doi.org/10.1038/s41421-020-0156-0 DOI |
43 | Schrezenmeier E, Dorner T (2020) Mechanisms of action of hydroxychloroquine and chloroquine: implications for rheumatology. Nat Rev Rheumatol 16:1-12. https://doi.org/10.1038/s41584-020-0372-x DOI |
44 | Savarino A, Di Trani L, Donatelli I, Cauda R, Cassone A (2006) New insights into the antiviral effects of chloroquine. Lancet Infect Dis 6:67-69. https://doi.org/10.1016/S1473-3099(06)70361-9 DOI |
45 | Seitz M, Valbracht J, Quach J, Lotz M (2003) Gold sodium thiomalate and chloroquine inhibit cytokine production in monocytic THP-1 cells through distinct transcriptional and posttranslational mechanisms. J Clin Immunol 23:477-484. https://doi.org/10.1023/B:JOCI.0000010424.41475.17 DOI |
46 | Brumlik MJ, Nkhoma S, Kious MJ, Thompson GR 3rd, Patterson TF, Siekierka JJ, Anderson TJ, Curiel TJ (2011) Human p38 mitogen-activated protein kinase inhibitor drugs inhibit Plasmodium falciparum replication. Exp Parasitol 128:170-175. https://doi.org/10.1016/j.exppara.2011.02.016 DOI |
47 | Grundmann M, Mikulikova I, Vrublovsky P (1971) Tissue distribution of subcutaneously administered chloroquine in the rat. Arzneimittelforschung 21:573. PMID: 5108164 |
48 | Cortegiani A, Ingoglia G, Ippolito M, Giarratano A, Einav S (2020) A systematic review on the efficacy and safety of chloroquine for the treatment of COVID-19. J Crit Care 27:279-283. https://doi.org/10.1016/j.jcrc.2020.03.005 DOI |
49 | Lisney AR, Szelinski F, Reiter K, Burmester GR, Rose T, Dorner T (2017) High maternal expression of SIGLEC1 on monocytes as a surrogate marker of a type I interferon signature is a risk factor for the development of autoimmune congenital heart block. Ann Rheum Dis 76:1476-1480. https://doi.org/10.1136/annrheumdis-2016-210927 DOI |
50 | Lacroix I, Benevent J, Damase-Michel C (2020) Chloroquine and hydroxychloroquine during pregnancy: what do we know? Therapie 75:384-385. https://doi.org/10.1016/j.jinf.2020.05.004 DOI |
51 | Huang M, Tang T, Pang P, Li M, Ma R, Lu J et al (2020) Treating COVID-19 with chloroquine. J Mol Cell Biol 12:322-325. https://doi.org/10.1093/jmcb/mjaa014 DOI |
52 | Bessiere F, Roccia H, Deliniere A, Charriere R, Chevalier P, Argaud L et al (2020) Assessment of QT intervals in a case series of patients with Coronavirus disease 2019 (COVID-19) infection treated with hydroxychloroquine alone or in combination with azithromycin in an intensive care Unit. JAMA Cardiol 5:1067-1069. https://doi.org/10.1001/jamac ardio.2020.1787 DOI |
53 | Wang M, Cao R, Zhang L, Yang X, Liu J, Xu M et al (2020) Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Res 30:269-271. https://doi.org/10.1038/s41422-020-0282-0 DOI |
54 | Mingo RM, Simmons JA, Shoemaker CJ et al (2015) Ebola virus and severe acute respiratory syndrome coronavirus display late cell entry kinetics: evidence that transport to NPC1+ endolysosomes is a rate-defining step. J Virol 89:2931-2943. https://doi.org/10.1128/JVI.03398-14 DOI |
55 | McChesney E-W, Conway W, Banks W, Rogers J, Shekosky J, Grace A et al (1966) Studies of the metabolism of some compounds of the 4-amino-7-chloroquinoline series. J Pharmacol Exp Ther 151:482-493. PMID: 4957157 |
56 | Chen J, Liu D, Liu L, Liu P, Xu Q, Xia L et al (2020) A pilot study of hydroxychloroquine in treatment of patients with common coronavirus disease-19 (COVID-19). J Zhejiang Univ (Med Sci) 49:215-219. https://doi.org/10.3785/j.issn.1008-9292.2020.03.03 DOI |
57 | Mercuro NJ, Yen CF, Shim DJ, Maher TR, McCoy CM, Zimetbaum PJ et al (2020) Risk of QT interval prolongation associated with use of hydroxychloroquine with or without concomitant azithromycin among hospitalized patients testing positive for Coronavirus Disease 2019 (COVID-19). JAMA Cardiol 5:1036-1041. PMID: 32936252 DOI |
58 | Mackenzie AH (1983) Pharmacologic actions of 4-aminoquinoline compounds. Am J Med 75:5-10. https://doi.org/10.1016/0002-9343(83)91264-0 DOI |
59 | Wetsteyn J, De Vries P, Oosterhuis B, Van Boxtel C (1995) The pharmacokinetics of three multiple dose regimens of chloroquine: implications for malaria chemoprophylaxis. Br J Clin Pharmacol 39:696-699. https://doi.org/10.1111/j.1365-2125.1995.tb05731.x DOI |
60 | Costedoat-Chalumeau N, Dunogue B, Leroux G, Morel N, Jallouli M, Le Guern V et al (2015) A critical review of the effects of hydroxychloroquine and chloroquine on the eye. Clin Rev Allergy Immunol 49:317-326. https://doi.org/10.1007/s12016-015-8469-8 DOI |
61 | Gay B, Bernard E, Solignat M, Chazal N, Devaux C, Briant L (2012) pH-dependent entry of chikungunya virus into Aedes albopictus cells. Infect Genet Evol 12:1275-1281. https://doi.org/10.1016/j.meegid.2012.02.003 DOI |
62 | Ksiazek TG, Erdman D, Goldsmith CS, Zaki SR, Peret T, Emery S et al (2003) A novel coronavirus associated with severe acute respiratory syndrome. N Engl J Med 348:1953-1966. https://doi.org/10.1056/NEJMoa030781 DOI |
63 | Yu IT-S, Qiu H, Tse LA, Wong TW (2014) Severe acute respiratory syndrome beyond Amoy Gardens: completing the incomplete legacy. Clin Infect Dis 58:683-686. https://doi.org/10.1093/cid/cit797 DOI |
64 | Li C, Zhu X, Ji X, Quanquin N, Deng Y-Q, Tian M et al (2017) Chloroquine, a FDA-approved drug, prevents Zika virus infection and its associated congenital microcephaly in mice. EBio-Medicine 24:189-194. https://doi.org/10.1016/j.ebiom.2017.09.034 DOI |
65 | Tsiang H, Superti F (1984) Ammonium chloride and chloroquine inhibit rabies virus infection in neuroblastoma cells. Adv Virol 81:377-382. https://doi.org/10.1007/BF01310010 DOI |
66 | Kwiek JJ, Haystead TA, Rudolph J (2004) Kinetic mechanism of quinone oxidoreductase 2 and its inhibition by the antimalarial quinolines. Biochemistry 43:4538-4547. https://doi.org/10.1021/bi035923w DOI |
67 | Olofsson S, Kumlin U, Dimock K, Arnberg N (2005) Avian influenza and sialic acid receptors: more than meets the eye? Lancet Infect Dis 5(3):184-188. https://doi.org/10.1016/S1473-3099(05)01311-3 DOI |
68 | Zhuang M-W, Cheng Y, Zhang J, Jiang X-M, Wang L, Deng J, Wang P-H (2020) Increasing host cellular receptor-angiotensin-converting enzyme 2 expression by coronavirus may facilitate 2019-nCoV (or SARS-CoV-2) infection. J Med Virol 92:2693-2701. https://doi.org/10.1002/jmv.26139 DOI |
69 | Savarino A, Gennero L, Sperber K, Boelaert J (2001) The anti-HIV-1 activity of chloroquine. J Clin Virol 20:131-135. https://doi.org/10.1016/S1386-6532(00)00139-6 DOI |
70 | Seferovic P, Ristic A, Maksimovic R, Simeunovic D, Ristic G, Radovanovic G et al (2006) Cardiac arrhythmias and conduction disturbances in autoimmune rheumatic diseases. Rheumatology 45:iv39-iv42. https://doi.org/10.1093/rheumatology/kel315 DOI |
71 | Bhatia M (1991) Chloroquine-induced psychiatric complications. Br J Psychiatry 159:735. https://doi.org/10.1192/bjp.159.5.735 DOI |
72 | Das P, Rai A, Chopra A, Philbrick K (2014) Psychosis likely induced by hydroxychloroquine in a patient with chronic Q fever: a case report and clinically relevant review of pharmacology. Psychosomatics 55:409-413. https://doi.org/10.1016/j.psym.2013.06.017 DOI |
73 | Hsu W, Chiu N, Huang S (2011) Hydroxychloroquine-induced acute psychosis in a systemic lupus erythematosus female. Acta Neuropsychiatr 23:318-319. https://doi.org/10.1111/j.1601-5215.2011.00575.x DOI |
74 | de Olano J, Howland MA, Su MK, Hoffman RS, Biary R (2019) Toxicokinetics of hydroxychloroquine following a massive overdose. Am J Emerg Med 37:2264.e5-2264.e8. https://doi.org/10.1016/j.ajem.2019.158387 DOI |
75 | Hughes JT, Esiri M, Oxbury J, Whitty C (1971) Chloroquine myopathy. QJM Int J Med 40:85-93. PMID: 4253656 |
76 | Sanghvi L, Mathur B (1965) Electrocardiogram after chloroquine and emetine. Circulation 32:281-289. https://doi.org/10.1161/01.CIR.32.2.281 DOI |
77 | Ooi EE, Chew JSW, Loh JP, Chua RC (2006) In vitro inhibition of human influenza A virus replication by chloroquine. Virol J 3:39. https://doi.org/10.1186/1743-422X-3-39 DOI |
78 | Riou B, Barriot P, Rimailho A, Baud FJ (1988) Treatment of severe chloroquine poisoning. N Engl J Med 318:1-6. https://doi.org/10.1056/NEJM198801073180101 DOI |
79 | Juurlink DN (2020) Safety considerations with chloroquine, hydroxychloroquine and azithromycin in the management of SARS-CoV-2 infection. CMAJ 192:E450-E453. https://doi.org/10.1503/cmaj.200528 DOI |
80 | Maxwell NM, Nevin RL, Stahl S, Block J, Shugarts S, Wu AH et al (2015) Prolonged neuropsychiatric effects following management of chloroquine intoxication with psychotropic polypharmacy. Clin Case Rep 3:379. https://doi.org/10.1002/ccr3.238 DOI |
81 | Kim K-A, Park J-Y, Lee J-S, Lim S (2003) Cytochrome P450 2C8 and CYP3A4/5 are involved in chloroquine metabolism in human liver microsomes. Arch Pharmacal Res 26:631-637. https://doi.org/10.1007/BF02976712 DOI |
82 | Tulpule A, Krishnaswamy K (1982) Effect of food on bioavailability of chloroquine. Eur J Clin Pharmacol 23:271-273. https://doi.org/10.1007/BF00547567 DOI |
83 | Tricou V, Minh NN, Van TP, Lee SJ, Farrar J, Wills B et al (2010) A randomized controlled trial of chloroquine for the treatment of dengue in Vietnamese adults. PLoS Negl Trop Dis 4:e785. https://doi.org/10.1371/journ al. pntd. 00007 85 DOI |
84 | Giovanella F, Ferreira GK, Pra SDD, Carvalho-Silva M, Gomes LM, Scaini G et al (2015) Effects of primaquine and chloroquine on oxidative stress parameters in rats. An Acad Bras Cienc 87:1487-1496.https://doi.org/10.1590/0001-3765201520140637 DOI |
85 | Shadnia S, Ebadollahi-Natanzi A, Ahmadzadeh S, Karami- Mohajeri S, Pourshojaei Y, Rahimi HR (2018) Delayed death following paraquat poisoning: three case reports and a literature review. Toxicol Res 7:745-753. https://doi.org/10.1039/c8tx00120k.3 DOI |
86 | Reghunathan R, Jayapal M, Hsu L-Y, Chng H-H, Tai D, Leung BP et al (2005) Expression profile of immune response genes in patients with severe acute respiratory syndrome. BMC Immunol 6:2. https://doi.org/10.1186/1471-2172-6-2 DOI |
87 | Ofori-Adjei D, Ericsson O (1985) Chloroquine in nail clippings. Lancet 2:331. https://doi.org/10.1016/S0140-6736(85)90377-0 DOI |
88 | Briant L, Robert-Hebmann V, Acquaviva C, Pelchen-Matthews A, Marsh M, Devaux C (1998) The protein tyrosine kinase p56 lck is required for triggering NF-κB activation upon interaction of human immunodeficiency virus type 1 envelope glycoprotein gp120 with cell surface CD4. J Virol 72:6207-6214. https://doi.org/10.1128/JVI.72.7.6207-6214.1998 DOI |
89 | Gustafsson L, Lindstrom B, Grahnen A, Alvan G (1987) Chloroquine excretion following malaria prophylaxis. Br J Clin Pharmacol 24:221-224. https://doi.org/10.1111/j.1365-2125.1987.tb03165.x DOI |
90 | Ette EI, Essien EE, Thomas WO, Brown-Awala EA (1989) Pharmacokinetics of chloroquine and some of its metabolites in healthy volunteers: a single dose study. J Clin Pharmacol 29:457-462. https://doi.org/10.1128/AAC.01269-09 DOI |
91 | Wellems TE, Plowe CV (2001) Chloroquine-resistant malaria. J Infect Dis 184:770-776. https://doi.org/10.1086/322858 DOI |
92 | Musabayane C, Cooper R, Osim E, Balment R (2000) Renal electrolyte and fluid handling in the rat following chloroquine and/or ethanol administration. Gen Pharmacol Vasc Syst 34:43-51. https://doi.org/10.1016/S0306-3623(00)00045-8 DOI |
93 | Musabayane CT, Cooper RG, Rao PVVP, Balment RJ (2000) Effects of ethanol on the changes in renal fluid and electrolyte handling and kidney morphology induced by long-term chloroquine administration to rats. Alcohol 22:129-138. https://doi.org/10.1016/S0741-8329(00)00110-5 DOI |
94 | Melles RB, Marmor MF (2014) The risk of toxic retinopathy in patients on long-term hydroxychloroquine therapy. JAMA Ophthalmol 132:1453-1460. https://doi.org/10.1001/jamaophthalmol.2014.3459 DOI |
95 | Becker K, Tilley L, Vennerstrom JL, Roberts D, Rogerson S, Ginsburg H (2004) Oxidative stress in malaria parasite-infected erythrocytes: host-parasite interactions. Int J Parasitol 34:163-189. https://doi.org/10.1016/j.ijpara.2003.09.011 DOI |
96 | Wallace DJ, Trobe J (2020) Antimalarial drugs in the treatment of rheumatic disease. UpToDate, Waltham |
97 | Ducharme J, Farinotti R (1996) Clinical pharmacokinetics and metabolism of chloroquine. Clin Pharmacokinet 31:257-274. https://doi.org/10.2165/00003 088-19963 1040-00003 DOI |
98 | Frisk-Holmberg M, Bergqvist Y, Englund U (1983) Chloroquine intoxication. Br J Clin Pharmacol 15:502. https://doi.org/10.1111/j.1365-2125.1983.tb01540.x DOI |
99 | Yan Y, Zou Z, Sun Y, Li X, Xu K-F, Wei Y et al (2013) Antimalaria drug chloroquine is highly effective in treating avian influenza A H5N1 virus infection in an animal model. Cell Res 23:300-302. https://doi.org/10.1038/cr.2012.165 DOI |
100 | Roques P, Thiberville S-D, Dupuis-Maguiraga L, Lum F-M, Labadie K, Martinon F et al (2018) Paradoxical effect of chloroquine treatment in enhancing chikungunya virus infection. Viruses 10:268. https://doi.org/10.3390/v10050268 DOI |
101 | Akpovwa H (2016) Chloroquine could be used for the treatment of filoviral infections and other viral infections that emerge or emerged from viruses requiring an acidic pH for infectivity. Cell Biochem Funct 34:191-196. https://doi.org/10.1002/cbf.3182 DOI |
102 | Peymani P, Yeganeh B, Sabour S, Geramizadeh B, Fattahi MR, Keyvani H et al (2016) New use of an old drug: chloroquine reduces viral and ALT levels in HCV non-responders (a randomized, triple-blind, placebo-controlled pilot trial). Can J Physiol Pharmacol 94:613-619. https://doi.org/10.1139/cjpp-2015-0507 DOI |
103 | Gao J, Tian Z, Yang X (2020) Breakthrough: chloroquine phosphate has shown apparent efficacy in treatment of COVID-19 associated pneumonia in clinical studies. Biosci Trends 14:72-73. https://doi.org/10.5582/BST.2020.01047 DOI |
104 | Plantone D, Koudriavtseva T (2018) Current and future use of chloroquine and hydroxychloroquine in infectious, immune, neoplastic, and neurological diseases: a mini-review. Clin Drug Investig 38:653-671. https://doi.org/10.1007/s40261-018-0656-y DOI |
105 | Sriboonvorakul N, Ghose A, Hassan MMU, Hossain MA, Faiz MA, Pukrittayakamee S et al (2018) Acidosis and acute kidney injury in severe malaria. Malar J 17:128. https://doi.org/10.1186/s12936-018-2274-9 DOI |
106 | Cabral RTS, Klumb EM, Couto MINN, Carneiro S (2019) Evaluation of toxic retinopathy caused by antimalarial medications with spectral domain optical coherence tomography. Arq Bras Oftalmol 82:12-17. https://doi.org/10.5935/0004-2749.20190002 DOI |
107 | Jorge A, Ung C, Young LH, Melles RB, Choi HK (2018) Hydroxychloroquine retinopathy-implications of research advances for rheumatology care. Nat Rev Rheumatol 14:693-703. https://doi.org/10.1038/s41584-018-0111-8 DOI |
108 | Page F (1951) Treatment of lupus erythematosus with mepacrine. Lancet 258:755-758. https://doi.org/10.1016/S0140-6736(51)91643-1 DOI |
109 | Abdulaziz N, Shah AR, McCune WJ (2018) Hydroxychloroquine: balancing the need to maintain therapeutic levels with ocular safety an update. Curr Opin Rheumatol 30:249-255. https://doi.org/10.1097/BOR.0000000000000500 DOI |
110 | Lee JY, Vinayagamoorthy N, Han K, Kwok SK, Ju JH, Park KS et al (2016) Association of polymorphisms of cytochrome P450 2D6 with blood hydroxychloroquine levels in patients with systemic lupus erythematosus. Arthritis Rheumatol 68:184-190. https://doi.org/10.1002/art.39402 DOI |
111 | Leppert W (2011) CYP2D6 in the metabolism of opioids for mild to moderate pain. Pharmacology 87:274-285. https://doi.org/10.1159/000326085 DOI |
112 | Projean D, Baune B, Farinotti R, Flinois JP, Beaune P, Taburet AM, Ducharme J (2003) In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos 31:748-754. https://doi.org/10.1124/dmd.31.6.748 DOI |
113 | Back DJ, Purba HS, Staiger C, Orme MLE, Breckenridge AM (1983) Inhibition of drug metabolism by the antimalarial drugs chloroquine and primaquine in the rat. Biochem Pharmacol 32:257-263. https://doi.org/10.1007/BF03188819 DOI |
114 | Rainsford K, Parke AL, Clifford-Rashotte M, Kean W (2015) Therapy and pharmacological properties of hydroxychloroquine and chloroquine in treatment of systemic lupus erythematosus, rheumatoid arthritis and related diseases. Inflammopharmacology 23:231-269. https://doi.org/10.1007/s10787-015-0239-y DOI |
115 | Keyaerts E, Vijgen L, Maes P, Neyts J, Van Ranst M (2004) In vitro inhibition of severe acute respiratory syndrome coronavirus by chloroquine. Biochem Biophys Res Commun 323:264-268. https://doi.org/10.1016/j.bbrc.2004.08.085 DOI |
116 | Tan YW, Yam WK, Sun J, Chu JJH (2018) An evaluation of chloroquine as a broad-acting antiviral against hand, foot and mouth disease. Antivir Res 149:143-149. https://doi.org/10.1016/j.antiviral.2017.11.017 DOI |
117 | Zhou P, Yang X-L, Wang X-G, Hu B, Zhang L, Zhang W et al (2020) A pneumonia outbreak associated with a new coronavirus of probable bat origin. Nature 579:270-273. https://doi.org/10.1038/s41586-020-2012-7 DOI |
118 | Tse EG, Korsik M, Todd MH (2019) The past, present and future of anti-malarial medicines. Malar J 18:93. https://doi.org/10.1186/s12936-019-2724-z DOI |
119 | Murugavel P, Pari L (2004) Attenuation of chloroquine-induced renal damage by α-lipoic acid: possible antioxidant mechanism. Ren Fail 26:517-524. https://doi.org/10.1081/JDI-200031761 DOI |
120 | Boyle PJ, Justice K, Krentz AJ, Nagy RJ, Schade DS (1993) Octreotide reverses hyperinsulinemia and prevents hypoglycemia induced by sulfonylurea overdoses. J Clin Endocrinol Metab 76:752-756. https://doi.org/10.1210/jcem.76.3.8445035 DOI |
121 | Paton NI, Lee L, Xu Y, Ooi EE, Cheung YB, Archuleta S et al (2011) Chloroquine for influenza prevention: a randomised, double- blind, placebo controlled trial. Lancet Infect Dis 11:677-683. https://doi.org/10.1016/s1473-3099(11)70065-2 DOI |
122 | Gautret P, Lagier J-C, Parola P, Meddeb L, Mailhe M, Doudier B et al (2020) Hydroxychloroquine and azithromycin as a treatment of COVID-19: results of an open-label non-randomized clinical trial. Int J Antimicrob Agents 56:105949. https://doi.org/10.1016/j.ijantimicag.2020.105949 DOI |
123 | Jaeger A, Sauder P, Kopferschmitt J, Flesch F (1987) Clinical features and management of poisoning due to antimalarial drugs. Med Toxicol Adverse Drug Exp 2:242-273. https://doi.org/10.1007/BF03259868 DOI |
124 | Toennesmann E, Stroehmann I, Kandolf R, Wolburg H, Strach K, Musshoff F et al (2012) Cardiomyopathy caused by longterm treatment with chloroquine: a rare disease, or a rare diagnosis? J Rheumatol 39:1099-1103. https://doi.org/10.3899/jrheum.110959 DOI |
125 | Cervera A, Espinosa G, Cervera R, Font J, Ingelmo M (2001) Cardiac toxicity secondary to long term treatment with chloroquine. Ann Rheum Dis 60:301-302. https://doi.org/10.1136/ard.60.3.301 DOI |
126 | Chauhan A, Tikoo A (2015) The enigma of the clandestine association between chloroquine and HIV-1 infection. HIV Med 16:585-590. https://doi.org/10.1111/hiv.12295 DOI |
127 | Kim A, Sparks J, Liew J, Putman M, Berenbaum F, Duarte-Garcia A, COVID-19 Global Rheumatology Alliance et al (2020) A rush to judgment? Rapid reporting and dissemination of results and its consequences regarding the use of hydroxychloroquine for COVID-19. Ann Intern Med 30:M20-1223. https://doi.org/10.7326/M20-1223 DOI |
128 | Clemessy J-L, Taboulet P, Hoffman JR, Hantson P, Barriot P, Bismuth C et al (1996) Treatment of acute chloroquine poisoning: a 5-year experience. Crit Care Med 24:1189-1195. https://doi.org/10.1097/00003246-199607000-00021 DOI |
129 | Pastick KA, Okafor EC, Wang F, Lofgren SM, Skipper CP, Nicol MR, Pullen MF, Rajasingham R, McDonald EG, Lee TC, Schwartz IS (2020) Hydroxychloroquine and chloroquine for treatment of SARS-CoV-2 (COVID-19). Open Forum Infect Dis 7:ofaa130. https://doi.org/10.1093/ofid/ofaa130 DOI |
130 | Fossa AA, Wisialowski T, Duncan JN, Deng S, Dunne M (2007) Azithromycin/chloroquine combination does not increase cardiac instability despite an increase in monophasic action potential duration in the anesthetized guinea pig. Am J Trop Med Hyg 77:929-938. PMID: 17984356 DOI |
131 | Raoult D, Drancourt M, Vestris G (1990) Bactericidal effect of doxycycline associated with lysosomotropic agents on Coxiella burnetii in P388D1 cells. Antimicrob Agents Chemother 34:1512-1514. https://doi.org/10.1128/AAC.34.8.1512 DOI |
132 | Rolain J-M, Colson P, Raoult D (2007) Recycling of chloroquine and its hydroxyl analogue to face bacterial, fungal and viral infections in the 21st century. Int J Antimicrob Agents 30:297-308. https://doi.org/10.1016/j.ijantimicag.2007.05.015 DOI |
133 | Varki A (1997) Sialic acids as ligands in recognition phenomena. FASEB J 11(4):248-255. https://doi.org/10.1096/fasebj.11.4.9068613 DOI |
134 | Ladipo G, Essien E, Andy J (1983) Complete heart block in chronic chloroquine poisoning. Int J Cardiol 4:198-200. https://doi.org/10.1016/0167-5273(83)90136-5 DOI |
135 | Essien E, Ette E (1986) Effects of chloroquine and didesethylchloroquine on rabbit myocardium and mitochondria. J Pharm Pharmacol 38:543-546. https://doi.org/10.1111/j.2042-7158.1986.tb04620.x DOI |
136 | Bourrie M, Meunier V, Berger Y, Fabre G (1996) Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ther 277:321-332. PMID: 8613937 |
137 | McChesney E, Fasco M, Banks W, Kersch TB (1967) The metabolism of chloroquine in man during and after repeated oral dosage. J Pharmacol Exp Ther 158:323-331. PMID: 6065153 |
138 | Somer M, Kallio J, Pesonen U, Pyykko K, Huupponen R, Scheinin M (2000) Influence of hydroxychloroquine on the bioavailability of oral metoprolol. Br J Clin Pharmacol 49:549-554. https://doi.org/10.1046/j.1365-2125.2000.00197.x DOI |
139 | Marmor MF, Hu J (2014) Effect of disease stage on progression of hydroxychloroquine retinopathy. JAMA Ophthalmol 132:1105-1112. https://doi.org/10.1001/jamaophthalmol.2014.1099 DOI |
140 | Nampoory N, Nessim J, Gupta RK, Johny KV (1992) Drug interaction of chloroquine with ciclosporin. Nephron 62:108-109. https://doi.org/10.1159/000187007 DOI |
141 | Britton W, Kevau I (1978) Intentional chloroquine overdosage. Med J Aust 2:407-410. https://doi.org/10.5694/j.1326-5377.1978.tb76816.x DOI |
142 | Augustijns P, Geusens P, Verbeke N (1992) Chloroquine levels in blood during chronic treatment of patients with rheumatoid arthritis. Eur J Clin Pharmacol 42:429-433. https://doi.org/10.1007/BF00280130 DOI |
143 | Frisk-Holmberg M, Bergqvist Y, Termond E, Domeij-Nyberg B (1984) The single dose kinetics of chloroquine and its major metabolite desethylchloroquine in healthy subjects. Eur J Clin Pharmacol 26:521-530. https://doi.org/10.1007/BF00542151 DOI |
144 | Gustafsson L, Walker O, Alvan G, Beermann B, Estevez F, Gleisner L et al (1983) Disposition of chloroquine in man after single intravenous and oral doses. Br J Clin Pharmacol 15:471-479. https://doi.org/10.1111/j.1365-2125.1983.tb01532.x DOI |
145 | De Vries P, Oosterhuis B, Van Boxtel C (1994) Single-dose pharmacokinetics of chloroquine and its main metabolite in healthy volunteers. Drug Investig 8:143-149. https://doi.org/10.1007/BF03259430 DOI |
146 | Clemessy JL, Favier C, Borron SW, Hantson PE, Vicaut E, Baud FJ (1995) Hypokalaemia related to acute chloroquine ingestion. Lancet 346:877-880. https://doi.org/10.1016/S0140-6736(95)92711-5 DOI |
147 | Goyal V, Bordia A (1995) The hypoglycemic effect of chloroquine. J Assoc Physicians India 43:17-18. PMID: 9282631 |
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