Chemistry

Chloroquine (7-chloride-4-[4'-diethyleamino-1'-methyle-butylamino]-chinoline; molecular weight 319.89; chloroquine diphosphate molecular weight 515.9) is a white, crystalline, bitter-tasting powder. It is easily soluble in water and nearly unsoluble in ethanol and chloroform. Hydroxychloroquine is a derivative of chloroquine. As the latter does not significantly differ from chloroquine with respect to mode of action, pharmacokinetics, toxicology, side effects, and indications, both medicaments are discussed together.

One hundred fifty milligrams of the pure chloroquine base corresponds to approximately 250 mg of the commercially available chloroquine diphosphate, and 155 mg of hydroxychloroquine base corresponds to 200 mg of hydroxychloroquine sulfate. The conversion factor from chloroquine diphosphate to the base is approximately 0.6, and from the base to the salt is approximately 1.6. The factors for hydroxychloroquine are 0.77 and 1.29, respectively. The dosages in the text relate to the clinically relevant dosages of the salts.

Quinacrine (Atabrine, mepacrine, atebrin) (6-chloro-9-[1-methyl-4-diethyl-amine]butylamino-2-methoxyacridine) is available as the dihydrochloride. It is a

Table 26.1. Indications for chloroquine and hydroxychloroquine for the treatment of noninfectious diseases (according to Arneal et al. 2002, Barthel et al. 1996, Dereure and Guilhou 2002, Erhan et al. 2002, Khoury et al. 2003, Nguyen et al. 2002, Reeves et al. 2004, Wallace 1996, Ziering et al. 1993)

Proven effectivity

Strong indications for effectivity

Indication for effectivity in individual cases

Effectivity may evolve

Case records with positive effects

Lupus erythematodes

Chronic polyarthritis

Porphyria cutanea tarda Sarcoidosis (of the skin)

Hyperlipidemia (mainly during corticosteroid therapy)

Thromboembolic prophylaxis in case of antiphospholipid antibodies or intraopera-tively

Skin manifestations of dermatomyositis

Pseudogout

Primary Sjögren's syndrome

Polymorphous light eruption

REM syndrome Lymphocytic infiltration Interstitial or alveolear lung diseases in children Hypercalcemia Autoimmune thrombocyto-penia (with steroids)

Chronic fatigue syndrome Asthma

Giant cell arteriitis Lichen planus mucosae Atopic dermatitis Diabetes

Nonrheumatoid forms of inflammatory arthritis Prevention of acute GvHD

Proven by

Prospective controlled double-blind studies Prospective controlled double-blind studies Clinical studies Controlled clinical studies, partially double blind Controlled clinical studies

Controlled clinical studies

Large series of patients

Controlled double-blind study Controlled double-blind study (only laboratory improvement) Prospective double-blind study

Large series of patients Large series of patients Large series of patients

Large series of patients Patient series

Case reports Open clinical studies Large series of patients Open study Open study

Controlled clinical studies Large series of patients

Open clinical study

Sideroblastic anemia, chronic ulcerative stomatitis, epidermolysis bullosa, erythema anlare centrifugum, granuloma anulare, granulomatosis disciformis, light urticaria, Lyme disease, morphea, cutaneous mucinoses, panniculitis (Pfeiffer-Weber-Christian), pemphigus, polymyal-gia rheumatica, pseudolymphoma, pseudopelade Broq, chronic sinusitis, urticarial vasculitis, Well's syndrome, autoimmune urticaria, necrobiosis lipoidica

GvHD, graft versus host disease; REM, reticular erythematous mucinosis.

bright yellow, odorless, bitter crystalline, water-soluble powder that contains an approximately 80% quinacrine base. Tablets contain 100 mg of the dihydrochloride.

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