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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyHydroxychloroquine
Identification
- Name
- Hydroxychloroquine
- Accession Number
- DB01611
- Type
- Small Molecule
- Groups
- Approved
- Description
A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites.
- Structure
Structure for DB01611 (Hydroxychloroquine)
- Synonyms
- (+-)-Hydroxychloroquine
- (±)-hydroxychloroquine
- 2-((4-((7-chloro-4-Quinolyl)amino)pentyl)ethylamino)ethanol
- 2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol
- 7-chloro-4-(4-(Ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline
- 7-chloro-4-(4-(N-Ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline
- 7-chloro-4-[4-(N-Ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline
- 7-chloro-4-[5-(N-Ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline
- Hidroxicloroquina
- Hydroxychloroquinum
- NSC4375
- Oxichlorochine
- Oxichloroquine
- Polirreumin
- Product Ingredients
Ingredient UNII CAS InChI Key Hydroxychloroquine sulfate 8Q2869CNVH 747-36-4 JCBIVZZPXRZKTI-UHFFFAOYSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Plaquenil Tablet 200 mg/1 Oral Carilion Materials Management 2013-06-28 Not applicable US 
Plaquenil Tablet 200 mg/1 Oral Covis Pharmaceuticals, Inc. 2013-06-28 2017-12-31 US Plaquenil Tablet 200 mg/1 Oral Concordia Pharmaceuticals, Inc 2013-06-28 Not applicable US Plaquenil Tablet 200 mg/1 Oral Aphena Pharma Solutions Tennessee, Inc. 2013-06-28 Not applicable US Plaquenil Tablet 200 mg Oral Sanofi Aventis 1957-12-31 Not applicable Canada 
Plaquenil Tablet, film coated 200 mg/1 Oral Sanofi Aventis 1955-04-18 2017-12-22 US Plaquenil Tablet 200 mg/1 Oral Av Kare, Inc. 2016-07-14 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Apo-hydroxyquine Tablet 200 mg Oral Apotex Corporation 2002-12-13 Not applicable Canada Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Cardinal Health 1995-11-30 2018-01-31 US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral North Star Rx Llc 2015-12-18 Not applicable US Hydroxychloroquine Sulfate Tablet 200 mg/1 Oral Avera Mc Kennan Hospital 2015-03-24 2018-05-26 US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Directrx 2014-01-01 Not applicable US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Amneal Pharmaceuticals 2018-05-17 Not applicable US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Aphena Pharma Solutions Tennessee, Inc. 1995-11-30 Not applicable US Hydroxychloroquine Sulfate Tablet, coated 200 mg/1 Oral Watson Pharmaceuticals 1995-11-30 2016-03-05 US 
Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Enteral Mylan Pharmaceuticals 1998-06-18 Not applicable US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Sandoz 1995-11-30 Not applicable US - International/Other Brands
- Axokine (AstraZeneca) / Dolquine (Inmunosyn) / HCQS (Medigroup) / Polirreumin (TRB) / Quensyl (Sanofi)
- Categories
- Aminoquinolines
- Anti-Infective Agents
- Antimalarials
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Chloroquine
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Immunosuppressive Agents
- P-glycoprotein/ABCB1 Inhibitors
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Quinolines
- UNII
- 4QWG6N8QKH
- CAS number
- 118-42-3
- Weight
- Average: 335.872
Monoisotopic: 335.176440176 - Chemical Formula
- C18H26ClN3O
- InChI Key
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
- SMILES
- CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
Pharmacology
- Indication
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.
- Associated Conditions
- Pharmacodynamics
Hydroxychloroquine possesses antimalarial properties and also exerts a beneficial effect in lupus erythematosus (chronic discoid or systemic) and acute or chronic rheumatoid arthritis. The precise mechanism of action is not known.
- Mechanism of action
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.
Target Actions Organism ADNA cross-linking/alkylationHuman AToll-like receptor 7 antagonistHuman AToll-like receptor 9 antagonistHuman - Absorption
Very rapidly and completely absorbed following oral administration.
- Volume of distribution
- Not Available
- Protein binding
Approximately 45%.
- Metabolism
Partially hepatic, to active de-ethylated metabolites.
- Route of elimination
- Not Available
- Half life
Terminal elimination half-life In blood is approximately 50 days. In plasma it is approximately 32 days.
- Clearance
- Not Available
- Toxicity
Symptoms of overdose include headache, drowsiness, visual disturbances, cardiovascular collapse, and convulsions, followed by sudden and early respiratory and cardiac arrest. The electrocardiogram may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, and progressive bradycardia leading to ventricular fibrillation and/or arrest.
- Affected organisms
- Plasmodium
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Acebutolol The metabolism of Acebutolol can be decreased when combined with Hydroxychloroquine. Approved, Investigational Acepromazine The serum concentration of Acepromazine can be increased when it is combined with Hydroxychloroquine. Approved, Vet Approved Aceprometazine The serum concentration of Aceprometazine can be increased when it is combined with Hydroxychloroquine. Approved Acetyldigitoxin The serum concentration of Acetyldigitoxin can be increased when it is combined with Hydroxychloroquine. Approved Acetyldigoxin The serum concentration of Acetyldigoxin can be increased when it is combined with Hydroxychloroquine. Experimental Albendazole The serum concentration of Albendazole can be decreased when it is combined with Hydroxychloroquine. Approved, Vet Approved Albendazole oxide The serum concentration of Albendazole oxide can be decreased when it is combined with Hydroxychloroquine. Experimental Alimemazine The serum concentration of Alimemazine can be increased when it is combined with Hydroxychloroquine. Approved, Vet Approved Alprenolol The metabolism of Alprenolol can be decreased when combined with Hydroxychloroquine. Approved, Withdrawn Amiodarone The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Amiodarone. Approved, Investigational Arotinolol The metabolism of Arotinolol can be decreased when combined with Hydroxychloroquine. Investigational Arsenamide The serum concentration of Arsenamide can be decreased when it is combined with Hydroxychloroquine. Vet Approved Artemether The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Artemether. Approved Artemotil The serum concentration of Artemotil can be decreased when it is combined with Hydroxychloroquine. Approved Asenapine The metabolism of Asenapine can be decreased when combined with Hydroxychloroquine. Approved Atenolol The metabolism of Atenolol can be decreased when combined with Hydroxychloroquine. Approved Beclomethasone dipropionate The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Beclomethasone dipropionate. Approved, Investigational Befunolol The metabolism of Befunolol can be decreased when combined with Hydroxychloroquine. Experimental Benzatropine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Benzatropine. Approved Benzimidazole The serum concentration of Benzimidazole can be decreased when it is combined with Hydroxychloroquine. Experimental, Investigational Bephenium The serum concentration of Bephenium can be decreased when it is combined with Hydroxychloroquine. Experimental Bepridil The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Bepridil. Approved, Withdrawn Betaxolol The metabolism of Betaxolol can be decreased when combined with Hydroxychloroquine. Approved, Investigational Bevantolol The metabolism of Bevantolol can be decreased when combined with Hydroxychloroquine. Approved Bisoprolol The metabolism of Bisoprolol can be decreased when combined with Hydroxychloroquine. Approved Bithionol The serum concentration of Bithionol can be decreased when it is combined with Hydroxychloroquine. Withdrawn BL-1020 The serum concentration of BL-1020 can be increased when it is combined with Hydroxychloroquine. Investigational Bopindolol The metabolism of Bopindolol can be decreased when combined with Hydroxychloroquine. Approved Brompheniramine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Brompheniramine. Approved Bucindolol The metabolism of Bucindolol can be decreased when combined with Hydroxychloroquine. Investigational Budesonide The risk or severity of adverse effects can be increased when Budesonide is combined with Hydroxychloroquine. Approved Bufuralol The metabolism of Bufuralol can be decreased when combined with Hydroxychloroquine. Experimental, Investigational Bunamidine The serum concentration of Bunamidine can be decreased when it is combined with Hydroxychloroquine. Vet Approved Bupranolol The metabolism of Bupranolol can be decreased when combined with Hydroxychloroquine. Approved Cambendazole The serum concentration of Cambendazole can be decreased when it is combined with Hydroxychloroquine. Vet Approved Carbamazepine The risk or severity of adverse effects can be increased when Carbamazepine is combined with Hydroxychloroquine. Approved, Investigational Carbendazim The serum concentration of Carbendazim can be decreased when it is combined with Hydroxychloroquine. Investigational Carteolol The metabolism of Carteolol can be decreased when combined with Hydroxychloroquine. Approved Carvedilol The risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Carvedilol. Approved, Investigational Celiprolol The metabolism of Celiprolol can be decreased when combined with Hydroxychloroquine. Approved, Investigational Cetirizine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Cetirizine. Approved Chloroquine The serum concentration of Chloroquine can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Chlorphenamine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Chlorphenamine. Approved Chlorproethazine The serum concentration of Chlorproethazine can be increased when it is combined with Hydroxychloroquine. Experimental Chlorpromazine The serum concentration of Chlorpromazine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Ciclobendazole The serum concentration of Ciclobendazole can be decreased when it is combined with Hydroxychloroquine. Experimental Cimetidine The serum concentration of Cimetidine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Cinnarizine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Cinnarizine. Approved, Investigational Ciprofloxacin The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Ciprofloxacin. Approved, Investigational Clemastine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Clemastine. Approved, Investigational Cloranolol The metabolism of Cloranolol can be decreased when combined with Hydroxychloroquine. Experimental Clorsulon The serum concentration of Clorsulon can be decreased when it is combined with Hydroxychloroquine. Vet Approved Coumaphos The serum concentration of Coumaphos can be decreased when it is combined with Hydroxychloroquine. Vet Approved Cyclosporine The risk or severity of adverse effects can be increased when Cyclosporine is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Cymarin The serum concentration of Cymarin can be increased when it is combined with Hydroxychloroquine. Experimental Dapagliflozin The serum concentration of Dapagliflozin can be increased when it is combined with Hydroxychloroquine. Approved Dapsone The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Dapsone. Approved, Investigational Desaspidin The serum concentration of Desaspidin can be decreased when it is combined with Hydroxychloroquine. Experimental Desipramine The metabolism of Desipramine can be decreased when combined with Hydroxychloroquine. Approved, Investigational Deslanoside The serum concentration of Deslanoside can be increased when it is combined with Hydroxychloroquine. Approved Dexamethasone The risk or severity of adverse effects can be increased when Dexamethasone is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Dexbrompheniramine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Dexbrompheniramine. Approved Dichlorophene The serum concentration of Dichlorophene can be decreased when it is combined with Hydroxychloroquine. Vet Approved Dichlorvos The serum concentration of Dichlorvos can be decreased when it is combined with Hydroxychloroquine. Vet Approved Diethylcarbamazine The serum concentration of Diethylcarbamazine can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Digitoxin The serum concentration of Digitoxin can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Digoxin The serum concentration of Digoxin can be increased when it is combined with Hydroxychloroquine. Approved Digoxin Immune Fab (Ovine) The serum concentration of Digoxin Immune Fab (Ovine) can be increased when it is combined with Hydroxychloroquine. Approved Diltiazem The serum concentration of Diltiazem can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Dimenhydrinate The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Dimenhydrinate. Approved Diphenhydramine The risk or severity of QTc prolongation can be increased when Diphenhydramine is combined with Hydroxychloroquine. Approved, Investigational Dithiazanine The serum concentration of Dithiazanine can be decreased when it is combined with Hydroxychloroquine. Vet Approved Doramectin The serum concentration of Doramectin can be decreased when it is combined with Hydroxychloroquine. Vet Approved Doxylamine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Doxylamine. Approved, Vet Approved Emetine The serum concentration of Emetine can be decreased when it is combined with Hydroxychloroquine. Experimental Epanolol The metabolism of Epanolol can be decreased when combined with Hydroxychloroquine. Experimental Eprinomectin The serum concentration of Eprinomectin can be decreased when it is combined with Hydroxychloroquine. Vet Approved Esatenolol The metabolism of Esatenolol can be decreased when combined with Hydroxychloroquine. Experimental Esmolol The metabolism of Esmolol can be decreased when combined with Hydroxychloroquine. Approved Estradiol The serum concentration of Estradiol can be increased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Ethinyl Estradiol The serum concentration of Ethinyl Estradiol can be increased when it is combined with Hydroxychloroquine. Approved Everolimus The serum concentration of Everolimus can be increased when it is combined with Hydroxychloroquine. Approved Famotidine The risk or severity of QTc prolongation can be increased when Famotidine is combined with Hydroxychloroquine. Approved Febantel The serum concentration of Febantel can be decreased when it is combined with Hydroxychloroquine. Vet Approved Fenbendazole The serum concentration of Fenbendazole can be decreased when it is combined with Hydroxychloroquine. Vet Approved Fesoterodine The serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Hydroxychloroquine. Approved Flubendazole The serum concentration of Flubendazole can be decreased when it is combined with Hydroxychloroquine. Approved, Withdrawn Fluoxetine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Fluoxetine. Approved, Vet Approved Fluphenazine The serum concentration of Fluphenazine can be increased when it is combined with Hydroxychloroquine. Approved Fluticasone propionate The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Fluticasone propionate. Approved Gemcitabine The risk or severity of adverse effects can be increased when Gemcitabine is combined with Hydroxychloroquine. Approved Gitoformate The serum concentration of Gitoformate can be increased when it is combined with Hydroxychloroquine. Experimental Hexylresorcinol The serum concentration of Hexylresorcinol can be decreased when it is combined with Hydroxychloroquine. Approved Hydrocortisone The risk or severity of adverse effects can be increased when Hydrocortisone is combined with Hydroxychloroquine. Approved, Vet Approved Hydrocortisone acetate The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Hydrocortisone acetate. Approved, Vet Approved Hydrocortisone butyrate The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Hydrocortisone butyrate. Approved, Vet Approved Hydroxyzine The risk or severity of QTc prolongation can be increased when Hydroxyzine is combined with Hydroxychloroquine. Approved Hygromycin B The serum concentration of Hygromycin B can be decreased when it is combined with Hydroxychloroquine. Vet Approved Ibandronate The risk or severity of QTc prolongation can be increased when Ibandronate is combined with Hydroxychloroquine. Approved, Investigational Indenolol The metabolism of Indenolol can be decreased when combined with Hydroxychloroquine. Withdrawn Irinotecan The risk or severity of adverse effects can be increased when Irinotecan is combined with Hydroxychloroquine. Approved, Investigational Isradipine The risk or severity of QTc prolongation can be increased when Isradipine is combined with Hydroxychloroquine. Approved, Investigational Ivermectin The serum concentration of Ivermectin can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Labetalol The risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Labetalol. Approved Lamivudine The serum concentration of Lamivudine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Lamotrigine The serum concentration of Lamotrigine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Lanatoside C The serum concentration of Lanatoside C can be increased when it is combined with Hydroxychloroquine. Experimental Landiolol The metabolism of Landiolol can be decreased when combined with Hydroxychloroquine. Investigational Levamisole The serum concentration of Levamisole can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved, Withdrawn Levetiracetam The serum concentration of Levetiracetam can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Levobetaxolol The metabolism of Levobetaxolol can be decreased when combined with Hydroxychloroquine. Approved, Investigational Levobunolol The metabolism of Levobunolol can be decreased when combined with Hydroxychloroquine. Approved Loperamide The serum concentration of Loperamide can be increased when it is combined with Hydroxychloroquine. Approved Loratadine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Loratadine. Approved, Investigational Losartan The serum concentration of Losartan can be increased when it is combined with Hydroxychloroquine. Approved Lucanthone The serum concentration of Lucanthone can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational Lumefantrine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Lumefantrine. Approved Mebendazole The serum concentration of Mebendazole can be decreased when it is combined with Hydroxychloroquine. Approved, Vet Approved Mefloquine The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Mefloquine. Approved, Investigational Mepindolol The metabolism of Mepindolol can be decreased when combined with Hydroxychloroquine. Experimental Mepyramine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Mepyramine. Approved, Vet Approved Mesoridazine The serum concentration of Mesoridazine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Methimazole The risk or severity of adverse effects can be increased when Methimazole is combined with Hydroxychloroquine. Approved Methotrimeprazine The serum concentration of Methotrimeprazine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Methylene blue The serum concentration of Methylene blue can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Methylprednisolone The risk or severity of adverse effects can be increased when Methylprednisolone is combined with Hydroxychloroquine. Approved, Vet Approved Metildigoxin The serum concentration of Metildigoxin can be increased when it is combined with Hydroxychloroquine. Experimental Metipranolol The metabolism of Metipranolol can be decreased when combined with Hydroxychloroquine. Approved Metoclopramide The risk or severity of QTc prolongation can be increased when Metoclopramide is combined with Hydroxychloroquine. Approved, Investigational Metoprolol The risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Metoprolol. Approved, Investigational Milbemycin oxime The serum concentration of Milbemycin oxime can be decreased when it is combined with Hydroxychloroquine. Vet Approved Morantel The serum concentration of Morantel can be decreased when it is combined with Hydroxychloroquine. Vet Approved Moricizine The serum concentration of Moricizine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational, Withdrawn Moxidectin The serum concentration of Moxidectin can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Moxifloxacin The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Moxifloxacin. Approved, Investigational Nadolol The metabolism of Nadolol can be decreased when combined with Hydroxychloroquine. Approved Nebivolol The metabolism of Nebivolol can be decreased when combined with Hydroxychloroquine. Approved, Investigational Nicardipine The serum concentration of Nicardipine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Niclosamide The serum concentration of Niclosamide can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Nifedipine The serum concentration of Nifedipine can be increased when it is combined with Hydroxychloroquine. Approved Niridazole The serum concentration of Niridazole can be decreased when it is combined with Hydroxychloroquine. Experimental Oleandrin The serum concentration of Oleandrin can be increased when it is combined with Hydroxychloroquine. Experimental, Investigational Oltipraz The serum concentration of Oltipraz can be decreased when it is combined with Hydroxychloroquine. Investigational Omeprazole The serum concentration of Omeprazole can be increased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Ondansetron The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Ondansetron. Approved Ouabain The serum concentration of Ouabain can be increased when it is combined with Hydroxychloroquine. Approved Oxamniquine The serum concentration of Oxamniquine can be decreased when it is combined with Hydroxychloroquine. Approved Oxantel The serum concentration of Oxantel can be decreased when it is combined with Hydroxychloroquine. Experimental Oxfendazole The serum concentration of Oxfendazole can be decreased when it is combined with Hydroxychloroquine. Investigational, Vet Approved Oxibendazole The serum concentration of Oxibendazole can be decreased when it is combined with Hydroxychloroquine. Investigational, Vet Approved Oxprenolol The metabolism of Oxprenolol can be decreased when combined with Hydroxychloroquine. Approved Paroxetine The risk or severity of QTc prolongation can be increased when Paroxetine is combined with Hydroxychloroquine. Approved, Investigational Penbutolol The metabolism of Penbutolol can be decreased when combined with Hydroxychloroquine. Approved, Investigational Perazine The serum concentration of Perazine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Perphenazine The serum concentration of Perphenazine can be increased when it is combined with Hydroxychloroquine. Approved Peruvoside The serum concentration of Peruvoside can be increased when it is combined with Hydroxychloroquine. Experimental Pheniramine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Pheniramine. Approved Phenobarbital The serum concentration of Phenobarbital can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Pindolol The metabolism of Pindolol can be decreased when combined with Hydroxychloroquine. Approved, Investigational Piperazine The serum concentration of Piperazine can be decreased when it is combined with Hydroxychloroquine. Approved, Vet Approved Pitolisant The serum concentration of Pitolisant can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Platelet Activating Factor The metabolism of Platelet Activating Factor can be decreased when combined with Hydroxychloroquine. Experimental Practolol The metabolism of Practolol can be decreased when combined with Hydroxychloroquine. Approved Praziquantel The serum concentration of Praziquantel can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational, Vet Approved Prednisolone The risk or severity of adverse effects can be increased when Prednisolone is combined with Hydroxychloroquine. Approved, Vet Approved Prochlorperazine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Prochlorperazine. Approved, Vet Approved Promazine The serum concentration of Promazine can be increased when it is combined with Hydroxychloroquine. Approved, Vet Approved Promethazine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Promethazine. Approved, Investigational Propafenone The risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Propafenone. Approved Propericiazine The serum concentration of Propericiazine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Propiopromazine The serum concentration of Propiopromazine can be increased when it is combined with Hydroxychloroquine. Vet Approved Propranolol The risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Propranolol. Approved, Investigational Proscillaridin The serum concentration of Proscillaridin can be increased when it is combined with Hydroxychloroquine. Experimental Pyrvinium The serum concentration of Pyrvinium can be decreased when it is combined with Hydroxychloroquine. Approved Quetiapine The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Quetiapine. Approved Quinacrine The serum concentration of Quinacrine can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational Ranitidine The serum concentration of Ranitidine can be increased when it is combined with Hydroxychloroquine. Approved Rifampicin The serum concentration of Rifampicin can be increased when it is combined with Hydroxychloroquine. Approved Salbutamol The risk or severity of QTc prolongation can be increased when Salbutamol is combined with Hydroxychloroquine. Approved, Vet Approved Salmeterol The risk or severity of QTc prolongation can be increased when Salmeterol is combined with Hydroxychloroquine. Approved Sarilumab Sarilumab may increase the immunosuppressive activities of Hydroxychloroquine. Approved, Investigational Sitagliptin The serum concentration of Sitagliptin can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Sodium stibogluconate The serum concentration of Sodium stibogluconate can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational Sotalol The metabolism of Sotalol can be decreased when combined with Hydroxychloroquine. Approved Stibophen The serum concentration of Stibophen can be decreased when it is combined with Hydroxychloroquine. Experimental Sulfasalazine The risk or severity of adverse effects can be increased when Sulfasalazine is combined with Hydroxychloroquine. Approved Sumatriptan The serum concentration of Sumatriptan can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Suramin The serum concentration of Suramin can be decreased when it is combined with Hydroxychloroquine. Approved, Investigational Talinolol The metabolism of Talinolol can be decreased when combined with Hydroxychloroquine. Investigational Terbutaline The metabolism of Terbutaline can be decreased when combined with Hydroxychloroquine. Approved Terodiline The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Terodiline. Experimental Tertatolol The metabolism of Tertatolol can be decreased when combined with Hydroxychloroquine. Experimental Tetracycline The serum concentration of Tetracycline can be increased when it is combined with Hydroxychloroquine. Approved, Vet Approved Tetrandrine The risk or severity of adverse effects can be increased when Tetrandrine is combined with Hydroxychloroquine. Experimental Thiabendazole The serum concentration of Thiabendazole can be decreased when it is combined with Hydroxychloroquine. Approved, Vet Approved Thiazinam The serum concentration of Thiazinam can be increased when it is combined with Hydroxychloroquine. Experimental Thiethylperazine The serum concentration of Thiethylperazine can be increased when it is combined with Hydroxychloroquine. Withdrawn Thioproperazine The serum concentration of Thioproperazine can be increased when it is combined with Hydroxychloroquine. Approved Thioridazine The serum concentration of Thioridazine can be increased when it is combined with Hydroxychloroquine. Approved, Withdrawn Timolol The metabolism of Timolol can be decreased when combined with Hydroxychloroquine. Approved Topiramate The serum concentration of Topiramate can be increased when it is combined with Hydroxychloroquine. Approved Trichlorfon The serum concentration of Trichlorfon can be decreased when it is combined with Hydroxychloroquine. Vet Approved Triclabendazole The serum concentration of Triclabendazole can be decreased when it is combined with Hydroxychloroquine. Investigational Trifluoperazine The serum concentration of Trifluoperazine can be increased when it is combined with Hydroxychloroquine. Approved, Investigational Triflupromazine The serum concentration of Triflupromazine can be increased when it is combined with Hydroxychloroquine. Approved, Vet Approved Valproic Acid The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Valproic Acid. Approved, Investigational Vecuronium The serum concentration of Vecuronium can be increased when it is combined with Hydroxychloroquine. Approved Vemurafenib The risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Hydroxychloroquine. Approved Venlafaxine The serum concentration of Venlafaxine can be increased when it is combined with Hydroxychloroquine. Approved Verapamil The serum concentration of Verapamil can be increased when it is combined with Hydroxychloroquine. Approved Zidovudine The risk or severity of adverse effects can be increased when Zidovudine is combined with Hydroxychloroquine. Approved - Food Interactions
- Not Available
References
- Synthesis Reference
U.S. Patent 2,546,658.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015549
- KEGG Drug
- D08050
- KEGG Compound
- C07043
- PubChem Compound
- 3652
- PubChem Substance
- 46508459
- ChemSpider
- 3526
- ChEBI
- 5801
- ChEMBL
- CHEMBL1535
- Therapeutic Targets Database
- DAP000878
- PharmGKB
- PA164777036
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Hydroxychloroquine
- ATC Codes
- P01BA02 — Hydroxychloroquine
- AHFS Codes
- 08:30.08 — Antimalarials
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apotheca Inc.
- A-S Medication Solutions LLC
- Cadila Healthcare Ltd.
- Cardinal Health
- Caremark LLC
- Comprehensive Consultant Services Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Ipca Laboratories Ltd.
- Kaiser Foundation Hospital
- Major Pharmaceuticals
- Mallinckrodt Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Nucare Pharmaceuticals Inc.
- Ohm Laboratories Inc.
- Pharmedix
- Physicians Total Care Inc.
- Professional Co.
- Qualitest
- Ranbaxy Laboratories
- Resource Optimization and Innovation LLC
- Sandoz
- Sanofi-Aventis Inc.
- Southwood Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- United Research Laboratories Inc.
- Watson Pharmaceuticals
- West-Ward Pharmaceuticals
- Winthrop Us
- Zydus Pharmaceuticals
- Dosage forms
Form Route Strength Tablet Oral 200 mg/1 Tablet, coated Oral 200 mg/1 Tablet, film coated Enteral 200 mg/1 Tablet, film coated Oral 200 mg/1 Tablet Oral 200 mg - Prices
Unit description Cost Unit Hydroxychloroquine sulf powder 4.8USD g Plaquenil 200 mg tablet 3.14USD tablet Hydroxychloroquine Sulfate 200 mg tablet 1.28USD tablet Hydroxychloroquine 200 mg tablet 1.17USD tablet Plaquenil Sulfate 200 mg Tablet 0.66USD tablet Apo-Hydroxyquine 200 mg Tablet 0.35USD tablet Mylan-Hydroxychloroquine 200 mg Tablet 0.35USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 89-91 U.S. Patent 2,546,658. - Predicted Properties
Property Value Source Water Solubility 0.0261 mg/mL ALOGPS logP 3.87 ALOGPS logP 2.89 ChemAxon logS -4.1 ALOGPS pKa (Strongest Acidic) 15.59 ChemAxon pKa (Strongest Basic) 9.76 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 48.39 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 97.97 m3·mol-1 ChemAxon Polarizability 38.3 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9892 Blood Brain Barrier + 0.5602 Caco-2 permeable - 0.5154 P-glycoprotein substrate Substrate 0.8348 P-glycoprotein inhibitor I Non-inhibitor 0.7297 P-glycoprotein inhibitor II Inhibitor 0.5106 Renal organic cation transporter Non-inhibitor 0.5742 CYP450 2C9 substrate Non-substrate 0.8239 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Non-substrate 0.5384 CYP450 1A2 substrate Non-inhibitor 0.5864 CYP450 2C9 inhibitor Non-inhibitor 0.8457 CYP450 2D6 inhibitor Non-inhibitor 0.6111 CYP450 2C19 inhibitor Non-inhibitor 0.8782 CYP450 3A4 inhibitor Non-inhibitor 0.6287 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7058 Ames test AMES toxic 0.6907 Carcinogenicity Non-carcinogens 0.837 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6348 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6798 hERG inhibition (predictor II) Inhibitor 0.7173
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0f6t-3972000000-7c193125680c0c9e276f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Aminoquinolines and derivatives
- Direct Parent
- 4-aminoquinolines
- Alternative Parents
- Chloroquinolines / Secondary alkylarylamines / Aminopyridines and derivatives / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / 1,2-aminoalcohols / Azacyclic compounds / Primary alcohols show 3 more
- Substituents
- Chloroquinoline / 4-aminoquinoline / Haloquinoline / Aminopyridine / Secondary aliphatic/aromatic amine / Aryl chloride / Aryl halide / Pyridine / Benzenoid / Heteroaromatic compound show 18 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amino compound, organochlorine compound, secondary amino compound, primary alcohol, aminoquinoline (CHEBI:5801)
Targets
1. DNA
Yes
Cross-linking/alkylation
- General Function:
- Used for biological information storage.
- Specific Function:
- DNA contains the instructions needed for an organism to develop, survive and reproduce.
- Molecular Weight:
- 2.15 x 1012 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Koranda FC: Antimalarials. J Am Acad Dermatol. 1981 Jun;4(6):650-5. [PubMed:6165744]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR7 i...
- Gene Name
- TLR7
- Uniprot ID
- Q9NYK1
- Uniprot Name
- Toll-like receptor 7
- Molecular Weight
- 120920.8 Da
References
- Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957]
- Trevani AS, Chorny A, Salamone G, Vermeulen M, Gamberale R, Schettini J, Raiden S, Geffner J: Bacterial DNA activates human neutrophils by a CpG-independent pathway. Eur J Immunol. 2003 Nov;33(11):3164-74. [PubMed:14579285]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR9 i...
- Gene Name
- TLR9
- Uniprot ID
- Q9NR96
- Uniprot Name
- Toll-like receptor 9
- Molecular Weight
- 115858.665 Da
References
- Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957]
- Trevani AS, Chorny A, Salamone G, Vermeulen M, Gamberale R, Schettini J, Raiden S, Geffner J: Bacterial DNA activates human neutrophils by a CpG-independent pathway. Eur J Immunol. 2003 Nov;33(11):3164-74. [PubMed:14579285]
Enzymes
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Somer M, Kallio J, Pesonen U, Pyykko K, Huupponen R, Scheinin M: Influence of hydroxychloroquine on the bioavailability of oral metoprolol. Br J Clin Pharmacol. 2000 Jun;49(6):549-54. [PubMed:10848718]
Transporters
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Crowe A, Ilett KF, Karunajeewa HA, Batty KT, Davis TM: Role of P glycoprotein in absorption of novel antimalarial drugs. Antimicrob Agents Chemother. 2006 Oct;50(10):3504-6. doi: 10.1128/AAC.00708-06. Epub 2006 Aug 17. [PubMed:16917012]
- Plaquenil (hydroxychloroquine sulfate) - Drug Summary [Link]
Drug created on August 29, 2007 14:00 / Updated on August 15, 2018 09:52