Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H26ClN3O |
Molecular Weight | 335.872 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
InChI
InChIKey=XXSMGPRMXLTPCZ-UHFFFAOYSA-N
InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)
Hydroxychloroquine possesses antimalarial properties and also exerts a beneficial effect in lupus erythematosus (chronic discoid or systemic) and acute or chronic rheumatoid arthritis. Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown. Hydroxychloroquine is used for the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Hydroxychloroquine-induced vertigo. | 1975 Sep 1 |
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Antimalarial drugs in systemic lupus erythematosus: use in pregnancy. | 2001 |
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[Amphiphilic cationic drug myopathy, drug-induced lysosomal storage lipidosis]. | 2001 |
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Management of hepatitis C virus-related arthritis. | 2001 |
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Combination therapy with disease modifying anti-rheumatic drugs in rheumatoid arthritis. | 2001 |
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Treatment of rheumatoid arthritis: unknown long-term effects. | 2001 Apr |
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Leflunomide and rheumatoid arthritis: new preparation. Neither the safest nor the most effective slow-acting antirheumatic drug. | 2001 Apr |
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Early hydroxychloroquine macular toxicity. | 2001 Aug |
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Bromocriptine in rheumatic and autoimmune diseases. | 2001 Aug |
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Effect of hydroxychloroquine on progression of dementia in early Alzheimer's disease: an 18-month randomised, double-blind, placebo-controlled study. | 2001 Aug 11 |
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Systemic lupus erythematosus: current management. | 2001 Aug 6 |
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Angiooedema due to acquired deficiency of C1-esterase inhibitor associated with leucocytoclastic vasculitis. | 2001 Aug-Sep |
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[Combined basic therapeutic drugs. From individual hope to targeted use]. | 2001 Dec |
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Hydroxychloroquine retinopathy. | 2001 Dec |
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Progress in the treatment of rheumatoid arthritis. | 2001 Dec 12 |
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Fatal toxic epidermal necrolysis associated with hydroxychloroquine. | 2001 Jul |
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[Lymphedema of the upper limb, a complication of rheumatoid polyarthritis]. | 2001 Jun 30 |
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Hydroxychloroquine sulphate inhibits in vitro apoptosis of circulating lymphocytes in patients with systemic lupus erythematosus. | 2001 Mar |
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Progression of hydroxychloroquine retinopathy after discontinuation of therapy: case report. | 2001 May |
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Vitamin D levels in women with systemic lupus erythematosus and fibromyalgia. | 2001 Nov |
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Dermatomyositis. | 2001 Nov 1 |
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[Psychiatric manifestations of lupus erythematosus systemic and Sjogren's syndrome]. | 2001 Nov-Dec |
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Modulation of hormones in the treatment of lupus. | 2001 Oct |
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Treatment of early seropositive rheumatoid arthritis: a two-year, double-blind comparison of minocycline and hydroxychloroquine. | 2001 Oct |
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Leflunomide for the treatment of systemic lupus erythematosus: comment on the article by McMurray. | 2001 Oct |
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Verrucous form of chilblain lupus erythematosus. | 2001 Sep |
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Treatment of hydroxychloroquine overdose. | 2001 Sep |
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Mycophenolate mofetil treatment of severe renal disease in pediatric onset systemic lupus erythematosus. | 2001 Sep |
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Ocular toxicity and antenatal exposure to chloroquine or hydroxychloroquine for rheumatic diseases. | 2001 Sep 8 |
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Dermatomyositis and Graves' disease. | 2001 Sep-Oct |
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Safety and efficacy of disease-modifying anti-rheumatic agents: focus on the benefits and risks of etanercept. | 2002 |
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Sustained normalization of cerebral blood-flow after iloprost therapy in a patient with neuropsychiatric systemic lupus erythematosus. | 2002 |
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Evidence of transplacental passage of hydroxychloroquine in humans. | 2002 Apr |
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Delay to institution of therapy and induction of remission using single-drug or combination-disease-modifying antirheumatic drug therapy in early rheumatoid arthritis. | 2002 Apr |
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Canadian Consensus Conference on hydroxychloroquine. | 2002 Apr |
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Randomized double blind trial of an extract from the pentacyclic alkaloid-chemotype of uncaria tomentosa for the treatment of rheumatoid arthritis. | 2002 Apr |
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Pharmacoeconomics of long-term treatment of rheumatoid arthritis. | 2002 Apr |
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[Primary Gougerot-Sjögren syndrome in a 13-year-old girl]. | 2002 Feb |
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How frequently and how soon should we screen our patients for the presence of antimalarial retinopathy? | 2002 Feb |
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Prescribing trends in disease modifying antirheumatic drugs for rheumatoid arthritis: a survey of practicing Canadian rheumatologists. | 2002 Feb |
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Antimalarial agents in pregnancy. | 2002 Feb 9 |
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Second-line drugs used in recent-onset rheumatoid arthritis in Brittany (France). | 2002 Jan |
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Chloroquine decreases cell-surface expression of tumour necrosis factor receptors in human histiocytic U-937 cells. | 2002 Jan |
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Treatment of severe immune thrombocytopenia associated with systemic lupus erythematosus: 59 cases. | 2002 Jan |
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Leflunomide induced fevers, thrombocytosis, and leukocytosis in a patient with relapsing polychondritis. | 2002 Jan |
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Hydroxychloroquine ototoxicity in a child with idiopathic pulmonary haemosiderosis. | 2002 Jan 11 |
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IgM antibodies against cytomegalovirus in SLE nephritis: viral infection or aspecific autoantibody? | 2002 Jan-Feb |
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Hydroxychloroquine reverses platelet activation induced by human IgG antiphospholipid antibodies. | 2002 Mar |
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Nonendemic pemphigus foliaceus in children. | 2002 Mar |
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The effectiveness of hydroxychloroquine in patients with type 2 diabetes mellitus who are refractory to sulfonylureas--a randomized trial. | 2002 Mar |
Patents
Sample Use Guides
Malaria: Suppression— In adults, 400 mg (=310 mg base) on exactly the same day of each week. In infants and children, the weekly suppressive dosage is 5 mg, calculated as base, per kg of body weight, but should not exceed the adult dose regardless of weight.
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/16/1820
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WHO-ESSENTIAL MEDICINES LIST |
2.4
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NCI_THESAURUS |
C271
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WHO-ATC |
P01BA02
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LIVERTOX |
489
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NDF-RT |
N0000175482
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NDF-RT |
N0000175713
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M6127
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HYDROXYCHLOROQUINE
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SUB08077MIG
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7198
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5521
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118-42-3
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D006886
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DB01611
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C557
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3652
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CHEMBL1535
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118-42-3
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204-249-8
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118-42-3
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796
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ACTIVE MOIETY