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Pharmacology of Chloroquine and Hydroxychloroquine

Browning, D., Pharmacology of Chloroquine and Hydroxychloroquine, 2014, 35-63, doi:10.1007/978-1-4939-0597-3_2
Apr 2014  
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HCQ for COVID-19
1st treatment shown to reduce risk in March 2020
*, now with p < 0.00000000001 from 411 studies, recognized in 46 countries.
No treatment is 100% effective. Protocols combine treatments. * >10% efficacy, ≥3 studies.
4,300+ studies for 75 treatments.
Review of the pharmacology of CQ and HCQ. Some notable points:
- HCQ and CQ are equipotent but CQ is more toxic, the therapeutic ratio is higher for HCQ.
- Concentrations in different tissues can vary >10x, in particular the concentration in the lung is much higher in animal experiments.
- Tissue uptake as a function of dosage is nonlinear.
33 preclinical studies support the efficacy of HCQ for COVID-19:
Browning et al., 4 Apr 2014, peer-reviewed, 1 author.
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Abstract: 2 Pharmacology of Chloroquine and Hydroxychloroquine Abbreviations 4AQR 4AQs ABW APC BCVA C CpG ODN CV CYP DFE DNA ERK FP GVF HC HIV HMG-CoA IBW IFN IL LD50 LDL M mRNA NG RA RNA RPE 4-Aminoquinoline retinopathy 4-Aminoquinolines (chloroquine and hydroxychloroquine) Actual body weight Antigen presenting cell Best corrected visual acuity Chloroquine CpG oligodeoxynucleotide Color vision Cytochrome P450 enzymes Dilated fundus examination Deoxyribonucleic acid Extracellular signal-regulated kinases Ferriprotoporphyrin IX Goldmann visual fields Hydroxychloroquine Human immunodeficiency virus 3-Hydroxy-3-methylglutarylcoenzyme A reductase Ideal body weight Interferon Interleukin Lethal dose 50 Low-density lipoprotein Mole Mitochondrial ribonucleic acid Not given Rheumatoid arthritis Ribonucleic acid Retinal pigment epithelium SARS SLE TLR TNF TNF-α V Severe acute respiratory syndrome Systemic lupus erythematosus Toll-like receptor Tumor necrosis factor Tumor necrosis factor α Volume of distribution This chapter covers the pharmacology of chloroquine and hydroxychloroquine, which is similar for both drugs [1], but the details are different. For example, both drugs are partially excreted in feces, but the proportions differ slightly—8–10 % for chloroquine and 15–24 % for hydroxychloroquine. Generally, whatever is said in this chapter about one drug can be assumed to apply to the other unless otherwise specified [1, 2]. Because both drugs are derivatives of a 4-aminoquinoline (4AQ) nucleus, they are referred to as 4AQs, and the retinopathy that they can cause is termed 4-aminoquinoline retinopathy (4AQR) [3]. Commonly used abbreviations in this chapter are collected in “Abbreviations” for reference. Each term will be first used in its full form, along with its abbreviation. 2.1 History In the 1600s, the Jesuits who proselytized Chile discovered from the Incas that the bark of the cinchona tree can cure malaria [4, 5]. Additional medicinal qualities of cinchona bark were described in the 1700s, and the British and Dutch transplanted these trees to Javan plantations in the early 1900s D.J. Browning, Hydroxychloroquine and Chloroquine Retinopathy, DOI 10.1007/978-1-4939-0597-3_2, © Springer Science+Business Media New York 2014 35 2 Pharmacology of Chloroquine and Hydroxychloroquine for the production of quinine. In 1894, Payne described the use of quinine to treat systemic lupus erythematosus (SLE) [6]. Other alkaloids contained in cinchona bark, such as pamaquine, were also successfully used to treat SLE [5]. When the Japanese army occupied Java in World War II, the natural supply of quinine was lost, and synthesis of antimalarials was pursued in the United States [7]. Quinacrine, a 9-aminoacridine compound, was first used, but had the unpleasant side effect of staining the skin and sclera yellow in a manner indistinguishable from icterus [8–10]. The 4AQs, chloroquine and hydroxychloroquine, were found to be effective as antimalarials and did not discolor the skin. Chloroquine was first synthesized in 1934 by Andersag of I.G. Farbenindustrie in a German effort to find drugs better than quinine [11]. The Germans lost interest in the drug when they judged it to be too toxic for use in man, but the Americans restudied the drug and found it to be effective against malaria and sufficiently safe [3, 7, 12]. Hydroxychloroquine was synthesized in 1946 and proposed as a safer alternative to chloroquine in 1955 [13]. Resistance to..
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Am J Med. 1983;75:321–6.', 'journal-title': 'Am J Med'}, { 'key': '2_CR107', 'doi-asserted-by': 'crossref', 'first-page': '71', 'DOI': '10.1097/00000441-195322510-00012', 'volume': '225', 'author': 'GG Haydu', 'year': '1953', 'unstructured': 'Haydu GG. Rheumatoid arthritis therapy: a rationale and the use of ' 'chloroquine diphosphate. Am J Med Sci. 1953;225:71–5.', 'journal-title': 'Am J Med Sci'}, { 'key': '2_CR108', 'doi-asserted-by': 'crossref', 'first-page': '80', 'DOI': '10.1191/096120398678919778', 'volume': '7', 'author': 'E Tsakonas', 'year': '1998', 'unstructured': 'The Canadian Hydroxychloroquine Study Group, Tsakonas E, Joseph L, ' 'Esdaile JM, Choquette D, et al. A long-term study of hydroxychloroquine ' 'withdrawal on exacerbations in systemic lupus erythematosus. Lupus. ' '1998;7:80–5.', 'journal-title': 'Lupus'}, { 'key': '2_CR109', 'doi-asserted-by': 'crossref', 'first-page': '1067', 'DOI': '10.7326/0003-4819-119-11-199312010-00002', 'volume': '119', 'author': 'P Clark', 'year': '1993', 'unstructured': 'Clark P, Cases E, Tugwell R, Medina C, Gheno C, Tenorio G, Orozco JA. ' 'Hydroxychloroquine compared with placebo in rheumatoid arthritis. Ann ' 'Intern Med. 1993;119:1067–71.', 'journal-title': 'Ann Intern Med.'}, { 'key': '2_CR110', 'doi-asserted-by': 'crossref', 'first-page': '206', 'DOI': '10.1016/0049-0172(87)90023-0', 'volume': '16', 'author': 'W Maksymowych', 'year': '1987', 'unstructured': 'Maksymowych W, Russell AS. Antimalarials in rheumatology: efficacy and ' 'safety. Semin Arthritis Rheum. 1987;16:206–21.', 'journal-title': 'Semin Arthritis Rheum'}, { 'key': '2_CR111', 'doi-asserted-by': 'crossref', 'first-page': '251', 'DOI': '10.1136/ard.15.3.251', 'volume': '15', 'author': 'A Freedman', 'year': '1956', 'unstructured': 'Freedman A. Chloroquine and rheumatoid arthritis. A short-term ' 'controlled trial. Ann Rheum Dis. 1956;15:251–7.', 'journal-title': 'Ann Rheum Dis'}, { 'key': '2_CR112', 'doi-asserted-by': 'crossref', 'first-page': '35', 'DOI': '10.1016/0002-9343(83)91268-8', 'volume': '75', 'author': 'RI Rynes', 'year': '1983', 'unstructured': 'Rynes RI. Ophthalmologic safety of long-term hydroxychloroquine sulfate ' 'treatment. Am J Med. 1983;75:35–9.', 'journal-title': 'Am J Med'}, { 'key': '2_CR113', 'doi-asserted-by': 'crossref', 'first-page': '649', 'DOI': '10.1016/S0002-9394(02)01392-2', 'volume': '133', 'author': 'DJ Browning', 'year': '2002', 'unstructured': 'Browning DJ. Hydroxychloroquine and chloroquine retinopathy: screening ' 'for drug toxicity. Am J Ophthalmol. 2002;133:649–56.', 'journal-title': 'Am J Ophthalmol'}, { 'key': '2_CR114', 'first-page': '808', 'volume': '26', 'author': 'C Wang', 'year': '1999', 'unstructured': 'Wang C, Fortin PR, Li Y, Panaritis T, Gans M, Esdaile JM. ' 'Discontinuation of antimalarial drugs in systemic lupus erythematosus. J ' 'Rheumatol. 1999;26:808–15.', 'journal-title': 'J Rheumatol'}, { 'key': '2_CR115', 'doi-asserted-by': 'crossref', 'first-page': '26', 'DOI': '10.1136/ard.41.Suppl_1.26', 'volume': '41', 'author': 'HE Paulus', 'year': '1982', 'unstructured': 'Paulus HE. An overview of benefit/risk of disease modifying treatment of ' 'rheumatoid arthritis as of today. Ann Rheum Dis. 1982;41:26–9.', 'journal-title': 'Ann Rheum Dis'}, { 'key': '2_CR116', 'doi-asserted-by': 'crossref', 'first-page': '1168', 'DOI': '10.1136/ard.2006.068676', 'volume': '66', 'author': 'GS Alarcon', 'year': '2007', 'unstructured': 'Alarcon GS, McGwin G, Bertoli AM, Fessler BJ, Calvo-Alen J, Bastian HM, ' 'Vila LM, Reveille JD. Effect of hydroxychloroquine on the survival of ' 'patients with systemic lupus erythematosus: data from LUMINA, ' 'multiethnic US cohort (LUMINA L). Ann Rheum Dis. 2007;66:1168–72.', 'journal-title': 'Ann Rheum Dis'}, { 'key': '2_CR117', 'doi-asserted-by': 'crossref', 'first-page': 'S4', 'DOI': '10.1177/0961203396005001031', 'volume': '5', 'author': 'R Fox', 'year': '1996', 'unstructured': 'Fox R. Anti-malarial drugs: possible mechanisms of action in autoimmune ' 'disease and prospects for drug development. Lupus. 1996;5:S4–10.', 'journal-title': 'Lupus'}, { 'key': '2_CR118', 'doi-asserted-by': 'crossref', 'first-page': '705', 'DOI': '10.1517/14740338.2011.566555', 'volume': '10', 'author': 'C Abarientos', 'year': '2011', 'unstructured': 'Abarientos C, Sperber K, Shapiro DL, Aronow WS, Chao CP, Ash JY. ' 'Hydroxychloroquine in systemic lupus erythematosus and rheumatoid ' 'arthritis and its safety in pregnancy. Expert Opin Drug Saf. ' '2011;10:705–14.', 'journal-title': 'Expert Opin Drug Saf'}, { 'key': '2_CR119', 'doi-asserted-by': 'crossref', 'first-page': '713', 'DOI': '10.1002/art.1780390502', 'volume': '39', 'author': 'American College of Rheumatology Ad Hoc Committee on Clinical Guidelines', 'year': '1996', 'unstructured': 'American College of Rheumatology Ad Hoc Committee on Clinical ' 'Guidelines. Guidelines for the management of rheumatoid arthritis. ' 'Arthritis Rheum. 1996;39:713–22.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR120', 'doi-asserted-by': 'crossref', 'first-page': '357', 'DOI': '10.1002/1529-0131(199902)42:2<357::AID-ANR19>3.0.CO;2-J', 'volume': '42', 'author': 'DE Furst', 'year': '1999', 'unstructured': 'Furst DE, Lindsley H, Baethge B, Botstein GR, Caldwell J, Dietz F, ' 'Ettlinger R, Golden HE, McLaughlin GE, Moreland LW, et al. Dose-loading ' 'with hydroxychloroquine improves the rate of response in early, active ' 'rheumatoid arthritis. Arthritis Rheum. 1999;42:357–65.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR121', 'doi-asserted-by': 'crossref', 'first-page': '729', 'DOI': '10.1002/jps.20792', 'volume': '96', 'author': 'AM Kaufmann', 'year': '2007', 'unstructured': 'Kaufmann AM, Krise JP. Lysosomal sequestration of amine-containing ' 'drugs: analysis and therapeutic implications. J Pharm Sci. ' '2007;96:729–46.', 'journal-title': 'J Pharm Sci.'}, { 'key': '2_CR122', 'doi-asserted-by': 'crossref', 'first-page': '161', 'DOI': '10.3109/03009747609165456', 'volume': '5', 'author': 'A Elman', 'year': '1976', 'unstructured': 'Elman A, Gullberg R, Nillson E, Rendahl I, Wachtmeister L. Choroquine ' 'retinopathy in patients with rheumatoid arthritis. Scand J Rheumatol. ' '1976;5:161–6.', 'journal-title': 'Scand J Rheumatol'}, { 'key': '2_CR123', 'doi-asserted-by': 'crossref', 'first-page': '101', 'DOI': '10.1136/bjo.53.2.101', 'volume': '53', 'author': 'SPB Percival', 'year': '1969', 'unstructured': 'Percival SPB, Behrman J. Ophthalmological safety of chloroquine. Br J ' 'Ophthalmol. 1969;53:101–9.', 'journal-title': 'Br J Ophthalmol.'}, { 'key': '2_CR124', 'doi-asserted-by': 'crossref', 'first-page': '188', 'DOI': '10.1136/ard.56.3.188', 'volume': '56', 'author': 'DJ Grierson', 'year': '1997', 'unstructured': 'Grierson DJ. Hydroxychloroquine and visual screening in a rheumatology ' 'outpatient clinic. Ann Rheum Dis. 1997;56:188–90.', 'journal-title': 'Ann Rheum Dis'}, { 'key': '2_CR125', 'doi-asserted-by': 'crossref', 'first-page': '418', 'DOI': '10.1016/j.ajo.2012.09.025', 'volume': '155', 'author': 'DJ Browning', 'year': '2013', 'unstructured': 'Browning DJ. Impact of the revised American Academy of Ophthalmology ' 'guidelines regarding hydroxychloroquine screening on actual practice. Am ' 'J Ophthalmol. 2013;155:418–28.', 'journal-title': 'Am J Ophthalmol'}, { 'key': '2_CR126', 'doi-asserted-by': 'crossref', 'first-page': '410', 'DOI': '10.1016/j.ajo.2013.04.011', 'volume': '156', 'author': 'DJ Browning', 'year': '2013', 'unstructured': 'Browning DJ. Reply to impact of the revised American Academy of ' 'Ophthalmology guidelines regarding hydroxychloroquine screening on ' 'actual practice. Am J Ophthalmol. 2013;156:410–1.', 'journal-title': 'Am J Ophthalmol'}, { 'key': '2_CR127', 'doi-asserted-by': 'crossref', 'first-page': '1318', 'DOI': '10.1136/ard.51.12.1318', 'volume': '51', 'author': 'EF Morand', 'year': '1992', 'unstructured': 'Morand EF, McCloud PI, Littlejohn GO. Continuation of long term ' 'treatment with hydroxychloroquine in systemic lupus erythematosus and ' 'rheumatoid arthritis. Ann Rheum Dis. 1992;51:1318–21.', 'journal-title': 'Ann Rheum Dis'}, { 'key': '2_CR128', 'doi-asserted-by': 'crossref', 'first-page': 'S16', 'DOI': '10.1177/0961203396005001051', 'volume': '5', 'author': 'M Petri', 'year': '1996', 'unstructured': 'Petri M. Hydroxychloroquine use in the Baltimore Lupus Cohort: effects ' 'on lipids, glucose and thrombosis. Lupus. 1996;5:S16–22.', 'journal-title': 'Lupus'}, { 'key': '2_CR129', 'doi-asserted-by': 'crossref', 'first-page': '1039', 'DOI': '10.1016/S0140-6736(68)91336-6', 'volume': '2', 'author': 'LJ Bruce-Chwatt', 'year': '1968', 'unstructured': 'Bruce-Chwatt LJ. Chloroquine blindness? Lancet. 1968;2:1039.', 'journal-title': 'Lancet'}, { 'key': '2_CR130', 'first-page': '176', 'volume': '86', 'author': 'H Reed', 'year': '1962', 'unstructured': 'Reed H, Campbell AA. Central scotomata following chloroquine therapy. ' 'Can Med Assoc J. 1962;86:176–8.', 'journal-title': 'Can Med Assoc J.'}, { 'key': '2_CR131', 'doi-asserted-by': 'crossref', 'first-page': '132', 'DOI': '10.1097/IEB.0b013e318220f383', 'volume': '12', 'author': 'M Easterbrook', 'year': '2011', 'unstructured': 'Easterbrook M. Clinical characteristics of hydroxychloroquine ' 'retinopathy. Evid Based ophthalmol. 2011;12:132–3.', 'journal-title': 'Evid Based ophthalmol.'}, { 'key': '2_CR132', 'doi-asserted-by': 'crossref', 'first-page': '1321', 'DOI': '10.1016/S0161-6420(03)00409-3', 'volume': '110', 'author': 'I Mavrikakis', 'year': '2003', 'unstructured': 'Mavrikakis I, Sfikakis PP, Mavrikakis E, Rougas K, Nikolaou A, ' 'Kostopoulos C, Mavrikakis M. The incidence of irreversible retinal ' 'toxicity in patients treated with hydroxychloroquine—a reappraisal. ' 'Ophthalmology. 2003;110:1321–6.', 'journal-title': 'Ophthalmology'}, { 'key': '2_CR133', 'doi-asserted-by': 'crossref', 'first-page': '270', 'DOI': '10.1136/bmj.1.5482.270', 'volume': '1', 'author': 'GB Arden', 'year': '1966', 'unstructured': 'Arden GB, Kolb H. Antimalarial therapy and early retinal changes in ' 'patients with rheumatoid arthritis. Br Med J. 1966;1:270–3.', 'journal-title': 'Br Med J'}, { 'key': '2_CR134', 'first-page': '692', 'volume': '12', 'author': 'DS Finbloom', 'year': '1985', 'unstructured': 'Finbloom DS, Silver K, Newsome DA, Gunkel R. Comparison of ' 'hydroxychloroquine and chloroquine use and the development of retinal ' 'toxicity. J Rheumatol. 1985;12:692–4.', 'journal-title': 'J Rheumatol'}, { 'key': '2_CR135', 'first-page': '67', 'volume': '6', 'author': 'A Savarino', 'year': '2006', 'unstructured': 'Savarino A, Trani LD, Donateli I, Cauda R, Cassone A. New insights into ' 'the antiviral effects of chloroquine. Reflection React. 2006;6:67–8.', 'journal-title': 'Reflection React'}, { 'key': '2_CR136', 'doi-asserted-by': 'crossref', 'first-page': '738', 'DOI': '10.1016/0002-9394(68)91300-7', 'volume': '66', 'author': 'RE Carr', 'year': '1968', 'unstructured': 'Carr RE, Henkind P, Rothfield N, Siegel IM. Ocular toxicity of ' 'antimalarial drugs-long-term follow-up. Am J Ophthalmol. 1968;66:738–44.', 'journal-title': 'Am J Ophthalmol'}, { 'key': '2_CR137', 'doi-asserted-by': 'crossref', 'first-page': '579', 'DOI': '10.1136/bmj.3.5618.579', 'volume': '3', 'author': 'SPB Percival', 'year': '1968', 'unstructured': 'Percival SPB, Meanock I. Chloroquine: ophthalmological safety and ' 'clinical assessment in rheumatoid arthritis. Br Med J. 1968;3:579–84.', 'journal-title': 'Br Med J'}, { 'key': '2_CR138', 'doi-asserted-by': 'crossref', 'first-page': '567', 'DOI': '10.1002/art.1780300512', 'volume': '30', 'author': 'DR Miller', 'year': '1987', 'unstructured': 'Miller DR, Fiechtner JJ, Carpenter JR, Brown RR, Stroshane RM, Stecher ' 'VJ. Plasma hydroxychloroquine concentrations and efficacy in rheumatoid ' 'arthritis. Arthritis Rheum. 1987;30:567–71.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR139', 'doi-asserted-by': 'crossref', 'first-page': '199', 'DOI': '10.1016/0090-6980(85)90185-6', 'volume': '30', 'author': 'JG Kench', 'year': '1985', 'unstructured': 'Kench JG, Seale JP, Temple DM, Tennant C. The effects of non-steroidal ' 'inhibitors of phospholipase A2 on leukotriene and histamine release from ' 'human and guinea-pig lung. Prostaglandins. 1985;30:199–208.', 'journal-title': 'Prostaglandins'}, { 'key': '2_CR140', 'first-page': '624P', 'volume': '14', 'author': 'M Frisk-Holmberg', 'year': '1982', 'unstructured': 'Frisk-Holmberg M, Bergqvist Y. Chloroquine disposition in man. Br J Clin ' 'Pharmacol. 1982;14:624P–6.', 'journal-title': 'Br J Clin Pharmacol'}, { 'key': '2_CR141', 'doi-asserted-by': 'crossref', 'first-page': '19', 'DOI': '10.1016/0002-9343(83)91266-4', 'volume': '75', 'author': 'G Salmeron', 'year': '1983', 'unstructured': 'Salmeron G, Lipsky PE. Immunosuppressive potential of antimalarials. Am ' 'J Med. 1983;75:19–24.', 'journal-title': 'Am J Med'}, { 'key': '2_CR142', 'first-page': '1874', 'volume': '20', 'author': 'SE Tett', 'year': '1993', 'unstructured': 'Tett SE, Day RO, Cutler DJ. Concentration-effect relationship of ' 'hydroxychloroquine in rheumatoid arthritis—a cross sectional study. J ' 'Rheumatol. 1993;20:1874–9.', 'journal-title': 'J Rheumatol'}, { 'key': '2_CR143', 'doi-asserted-by': 'crossref', 'first-page': '171', 'DOI': '10.3109/03009747809095649', 'volume': '7', 'author': 'FA Wollheim', 'year': '1978', 'unstructured': 'Wollheim FA, Hanson A, Laurell CB. Chloroquine treatment in rheumatoid ' 'arthritis. Scand J Rheumatol. 1978;7:171–6.', 'journal-title': 'Scand J Rheumatol'}, { 'key': '2_CR144', 'doi-asserted-by': 'crossref', 'first-page': '3284', 'DOI': '10.1002/art.22156', 'volume': '65', 'author': 'N Costedoat-Chalumeau', 'year': '2006', 'unstructured': 'Costedoat-Chalumeau N, Amoura Z, Hulot JS, Hummoud HA, Aymard G, Cacoub ' 'P, Frances C, Wechsler B, et al. Low blood concentration of ' 'hydroxychloroquine is a marker for and predictor of disease ' 'exacerbations in patients with systemic lupus erythematosus. Arthritis ' 'Rheum. 2006;65:3284–90.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR145', 'doi-asserted-by': 'crossref', 'first-page': '1257', 'DOI': '10.1038/2271257a0', 'volume': '227', 'author': 'S Ullberg', 'year': '1970', 'unstructured': 'Ullberg S, Lindquist NG, Sjostrand SE. Accumulation of ' 'chorio-retinotoxic drugs in the foetal eye. Nature. 1970;227:1257–8.', 'journal-title': 'Nature'}, { 'key': '2_CR146', 'doi-asserted-by': 'crossref', 'first-page': '3056', 'DOI': '10.1002/art.20648', 'volume': '50', 'author': 'R Cimaz', 'year': '2004', 'unstructured': 'Cimaz R, Brucato A, Meregalli E, Muscara M, Sergi P. Electroretinograms ' 'of children born to mothers treated with hydroxychloroquine during ' 'pregnancy and breast-feeding: comment on the article by ' 'Costedoat-Chalumeau et al. Arthritis Rheum. 2004;50:3056–7.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR147', 'doi-asserted-by': 'crossref', 'first-page': '1123', 'DOI': '10.1002/art.10150', 'volume': '46', 'author': 'N Costedoat-Chalumeau', 'year': '2002', 'unstructured': 'Costedoat-Chalumeau N, Amoura Z, Aymard G, Hong DLT, Wechsler B, et al. ' 'Evidence of transplacental passage of hydroxychloroquine in humans. ' 'Arthritis Rheum. 2002;46:1123–4.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR148', 'doi-asserted-by': 'crossref', 'first-page': '813', 'DOI': '10.1016/S0140-6736(01)06004-4', 'volume': '358', 'author': 'G Klinger', 'year': '2001', 'unstructured': 'Klinger G, Morad Y, Westall CA, Laskin C, Spitzer KA, Koren G, Buncic ' 'RJ. Ocular toxicity and antenatal exposure to chloroquine or ' 'hydroxychloroquine for rheumatic diseases. Lancet. 2001;358:813–4.', 'journal-title': 'Lancet'}, { 'key': '2_CR149', 'doi-asserted-by': 'crossref', 'first-page': '524', 'DOI': '10.1016/S0140-6736(02)07643-2', 'volume': '359', 'author': 'M Motta', 'year': '2002', 'unstructured': 'Motta M, Tincani A, Faden D, Zinzini E, Chirico G. Antimalarial agents ' 'in pregnancy. Lancet. 2002;359:524–5.', 'journal-title': 'Lancet'}, { 'key': '2_CR150', 'first-page': '1715', 'volume': '23', 'author': 'A Parke', 'year': '1996', 'unstructured': 'Parke A, West B. Hydroxychloroquine in pregnant patients with systemic ' 'lupus erythematosus. J Clin Rheumatol. 1996;23:1715–8.', 'journal-title': 'J Clin Rheumatol'}, { 'key': '2_CR151', 'doi-asserted-by': 'crossref', 'first-page': '3640', 'DOI': '10.1002/art.22159', 'volume': '54', 'author': 'MEB Clowse', 'year': '2006', 'unstructured': 'Clowse MEB, Magder L, Witter F, Petri M. Hydroxychloroquine in lupus ' 'pregnancy. Arthritis Rheum. 2006;54:3640–7.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR152', 'doi-asserted-by': 'crossref', 'first-page': 'S65', 'DOI': '10.1177/0961203396005001141', 'volume': '5', 'author': 'MA Khamashta', 'year': '1996', 'unstructured': 'Khamashta MA, Buchanan NMM, Hughes GRV. The use of hydroxychloroquine in ' 'lupus pregnancy: the British experience. Lupus. 1996;5:S65–6.', 'journal-title': 'Lupus'}, { 'key': '2_CR153', 'doi-asserted-by': 'crossref', 'first-page': '3207', 'DOI': '10.1002/art.11304', 'volume': '48', 'author': 'N Costedoat-Chalumeau', 'year': '2003', 'unstructured': 'Costedoat-Chalumeau N, Amoura Z, Duhaut P, Huong DLT, Sebbough D, ' 'Wechsler B, et al. Safety of hydroxychloroquine in pregnant patients ' 'with connective tissue disease: a study of one hundred thirty-three ' 'cases compared with a control group. Arthritis Rheum. 2003;48:3207–11.', 'journal-title': 'Arthritis Rheum'}, { 'key': '2_CR154', 'doi-asserted-by': 'crossref', 'first-page': '1055', 'DOI': '10.2165/00002018-200124140-00004', 'volume': '24', 'author': 'MB Borden', 'year': '2001', 'unstructured': 'Borden MB, Parke AL. Antimalarial drugs in systemic lupus erythematosus: ' 'use in pregnancy. Drug Saf. 2001;24:1055–83.', 'journal-title': 'Drug Saf'}, { 'key': '2_CR155', 'doi-asserted-by': 'crossref', 'first-page': '30', 'DOI': '10.1016/0002-9343(88)90359-2', 'volume': '85', 'author': 'A Parke', 'year': '1988', 'unstructured': 'Parke A. Antimalarial drugs and pregnancy. Am J Med. 1988;85:30–3.', 'journal-title': 'Am J Med'}, { 'key': '2_CR156', 'doi-asserted-by': 'crossref', 'first-page': '407', 'DOI': '10.1001/archotol.1964.00750040419009', 'volume': '80', 'author': 'CW Hart', 'year': '1964', 'unstructured': 'Hart CW, Naunton RF. The ototoxicity of chloroquine phosphate. 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J Exp Med. 2005;202:817–28.', 'journal-title': 'J Exp Med'}], 'container-title': 'Hydroxychloroquine and Chloroquine Retinopathy', 'original-title': [], 'language': 'en', 'link': [ { 'URL': '', 'content-type': 'unspecified', 'content-version': 'vor', 'intended-application': 'similarity-checking'}], 'deposited': { 'date-parts': [[2023, 7, 13]], 'date-time': '2023-07-13T00:16:58Z', 'timestamp': 1689207418000}, 'score': 1, 'resource': {'primary': {'URL': ''}}, 'subtitle': [], 'short-title': [], 'issued': {'date-parts': [[2014]]}, 'ISBN': ['9781493905966', '9781493905973'], 'references-count': 225, 'URL': '', 'relation': {}, 'subject': [], 'published': {'date-parts': [[2014]]}, 'assertion': [ { 'value': '4 April 2014', 'order': 1, 'name': 'first_online', 'label': 'First Online', 'group': {'name': 'ChapterHistory', 'label': 'Chapter History'}}, { 'value': 'This content has been made available to all.', 'name': 'free', 'label': 'Free to read'}]}
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